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  • CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/Heated Cocktail Pool
    From $645 per night (USD)

    HomeAway

    "CONCH HEAVEN" ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/Heated Cocktail Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    OLD TOWN LOCATION... A beautifully furnished and comfortable home, located a short distance from Duval Street.  Have bik ...

    From $645 per night (USD)

    HomeAway

    Details
  • CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
    From $495 per night (USD)

    VRBO

    "CAPTAIN'S QUARTERS" ~ A Vintage Key West Retreat that is full of Charm!!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    10

    HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE Once you step through the threshold of this Old Town ...

    From $495 per night (USD)

    VRBO

    Details
  • Key Largo 5/5, Pool, Jacuzzi, Outdoor Kitchen, Tiki Hut, 70’ wide dock, Ocean.
    From $975 per night (USD)

    HomeAway

    Key Largo 5/5, Pool, Jacuzzi, Outdoor Kitchen, Tiki Hut, 70’ wide dock, Ocean.

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    15

    This is a large 5 bed / 5 bath single family home which is located on a very quiet residential deep waterfront canal in ...

    From $975 per night (USD)

    HomeAway

    Details
  • ATLANTIC BREEZE ~ 2B/2BA Tropical Retreat w/ Pool, Fitness Area & Beach!
    From $245 per night (USD)

    VRBO

    "ATLANTIC BREEZE" ~ 2B/2BA Tropical Retreat w/ Pool, Fitness Area & Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...

    From $245 per night (USD)

    VRBO

    Details
  • SUNKISSED~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
    From $745 per night (USD)

    HomeAway

    "SUNKISSED"~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    JUST OFF DUVAL... Private single family home with three bedrooms and three bathrooms.  Open the rear French doors to a p ...

    From $745 per night (USD)

    HomeAway

    Details
  • Caribbean Fantazy 3bed 3bath with pool & dockage
    From $400 per night (USD)

    VRBO

    Caribbean Fantazy 3bed 3bath with pool & dockage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Seven Night Minimum NO EXCEPTIONS MAX OCCUPANCY: 8 (NO MATTER THE AGE) This rule is set by the City of Key Colony's res ...

    From $400 per night (USD)

    VRBO

    Details
  • Umbrella Drinks★Instaworthy Views★Ace Location +Free WIFI 2BR/2BA
    From $196 per night (USD)

    HomeAway

    Umbrella Drinks★Instaworthy Views★Ace Location +Free WIFI 2BR/2BA

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    **AVAILABLE AS A 1 BEDROOM- accommodating up to 4 people This beautiful one bedroom unit has been completely renovated ...

    From $196 per night (USD)

    HomeAway

    Details
  • P68 - 371 8th St in Key Colony Beach
    From $221 per night (USD)

    VRBO

    P68 - 371 8th St in Key Colony Beach

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    8

    This new construction duplex has it all! This beautiful home offers 3 bedrooms and 4 full bathrooms. A two story ...

    From $221 per night (USD)

    VRBO

    Details
  • Gorgeous Sunsets from Your Balcony in Moon Bay/Walk to nearby restaurants
    From $120 per night (USD)

    HomeAway

    Gorgeous Sunsets from Your Balcony in Moon Bay/Walk to nearby restaurants

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful condo located in Moonbay gated community with gorgeous sunsets from your private balcony. Enjoy kayaking, fis ...

    From $120 per night (USD)

    HomeAway

    Details
  • Doctors Arm waterfront home. 75 feet of dock with lots of privacy!
    From $209 per night (USD)

    VRBO

    Doctors Arm waterfront home. 75 feet of dock with lots of privacy!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    -2017 construction home on a 10,000 sf lot on a 40 foot wide canal. -Please note that there is a 28 day minimum rental p ...

    From $209 per night (USD)

    VRBO

    Details
  • Cuban Paradise-  Sleeps 6 on Duval-  One assigned parking space.
    From $290 per night (USD)

    HomeAway

    Cuban Paradise- Sleeps 6 on Duval- One assigned parking space.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape the stress and cares of your daily life with a vacation to the wonderful Cuban Paradise! This roomy 2 bedroom co ...

    From $290 per night (USD)

    HomeAway

    Details
  • Sunset Oasis at Moon Bay-perfect townhouse location, bay view
    From $95 per night (USD)

    VRBO

    Sunset Oasis at Moon Bay-perfect townhouse location, bay view

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Sunset Oasis is LOCATION, LOCATION, LOCATION LOCATION: Key Largo Florida, the perfect island with easy access to mainlan ...

    From $95 per night (USD)

    VRBO

    Details
  • P10 -  111A Alynn in Marathon
    From $154 per night (USD)

    HomeAway

    P10 - 111A Alynn in Marathon

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Canal Front, Marathon, Florida Escape to this luxurious paradise home designed for VIP guest. Relax and enjoy brea ...

    From $154 per night (USD)

    HomeAway

    Details
  • P51 - 751 98th St in Marathon
    From $234 per night (USD)

    VRBO

    P51 - 751 98th St in Marathon

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Oceanside, canal front home in Marathon. This 2 bedroom, 2 bath home has been beautifully updated inside and out. ...

    From $234 per night (USD)

    VRBO

    Details
  • P02 - 215 S Anglers in Marathon
    From $357 per night (USD)

    HomeAway

    P02 - 215 S Anglers in Marathon

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This 5 bedroom, 3-1/2 bath home is the ultimate in luxury! Built in true "Key West Style" with hardwood floors, tall cei ...

    From $357 per night (USD)

    HomeAway

    Details
  • P39 12399 Overseas Hwy Unit 10
    From $179 per night (USD)

    VRBO

    P39 12399 Overseas Hwy Unit 10

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Coral Lagoon Resort and Marina welcomes you to this immaculate 3 bedroom, 2.5 bath canal front townhome! This beau ...

    From $179 per night (USD)

    VRBO

    Details
  • P27 - 165 13th St in Key Colony Beach
    From $264 per night (USD)

    HomeAway

    P27 - 165 13th St in Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    This beautiful 3 bedroom, 2 bath home located in the very desirable Key Colony Beach, boasts a large open floor plan, pr ...

    From $264 per night (USD)

    HomeAway

    Details
  • Charming Craftsman Home in Key West
    From $250 per night (USD)

    VRBO

    Charming Craftsman Home in Key West

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy one of the most vibrant locations that Key West has to offer. The tropics meet historic craftsman charm at this ir ...

    From $250 per night (USD)

    VRBO

    Details
  • P62 - 262 Sadowksi, KCB
    From $179 per night (USD)

    HomeAway

    P62 - 262 Sadowksi, KCB

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Key Colony Beach, FL Beautiful duplex in Key Colony Beach with private fenced yard and private heat optional pool. ...

    From $179 per night (USD)

    HomeAway

    Details
  • P15 - 1330 Coury Dr in Key Colony Beach
    From $428 per night (USD)

    VRBO

    P15 - 1330 Coury Dr in Key Colony Beach

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    10

    Escape to this luxurious five bedroom paradise home designed for VIP guest. Enjoy the thirty foot dock with deep canal d ...

    From $428 per night (USD)

    VRBO

    Details
  • Tropical Breezes & Blowing Palm Trees Seaside Condo
    From $125 per night (USD)

    HomeAway

    Tropical Breezes & Blowing Palm Trees Seaside Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Paradise awaits you in this recently renovated, 2 bedroom and 2 bathroom, large CORNER UNIT in the highly desirable comm ...

    From $125 per night (USD)

    HomeAway

    Details
  • Lazy Tortuga 2 bed 2 bath Duplex
    From $125 per night (USD)

    VRBO

    Lazy Tortuga 2 bed 2 bath Duplex

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Seven Night Minimum, NO EXCEPTIONS. Maximum Occupancy: 4 (NO MATTER THE AGE) This is a regulation set up by Key Colony ...

    From $125 per night (USD)

    VRBO

    Details
  • P48 - 298 116th in Marathon
    From $171 per night (USD)

    HomeAway

    P48 - 298 116th in Marathon

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Charming two bedroom Keys Cottage. This single family, 2 bedroom 2 bath home is the perfect retreat to spend your ...

    From $171 per night (USD)

    HomeAway

    Details
  • OFF CALL ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!
    From $345 per night (USD)

    VRBO

    "OFF CALL" ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    GATED COMMUNITY CLOSE TO BOATING AND GOLFING... “OFF CALL” is a beautiful townhome in the Coral Hammock community; total ...

    From $345 per night (USD)

    VRBO

    Details
  • P63 - 250 4th Street
    From $171 per night (USD)

    HomeAway

    P63 - 250 4th Street

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    Offering a beautiful upscale duplex home in Key Colony Beach. Key Colony Beach is a small, friendly island with everythi ...

    From $171 per night (USD)

    HomeAway

    Details
  • P82 - 505 Corte Del Brisas
    From $321 per night (USD)

    VRBO

    P82 - 505 Corte Del Brisas

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    8

    Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! Completely remodeled an ...

    From $321 per night (USD)

    VRBO

    Details
  • MANGO MARGARITA~ 2 bedroom/2.5 bath close to the excitement of Duval!
    From $395 per night (USD)

    HomeAway

    "MANGO MARGARITA"~ 2 bedroom/2.5 bath close to the excitement of Duval!

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    LOCATION... Enjoy this convenient Old Town Location.  Located a block from Duval and a short walk or bike ride to everyt ...

    From $395 per night (USD)

    HomeAway

    Details
  • 'Oceanside Oasis' @ Kings Pointe: Direct Ocean Views & 3 BR'S
    From $150 per night (USD)

    VRBO

    'Oceanside Oasis' @ Kings Pointe: Direct Ocean Views & 3 BR'S

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this bea ...

    From $150 per night (USD)

    VRBO

    Details
  • Great feel of a home away from home.

You will enjoy a very clean and tidy house
    From $100 per night (USD)

    HomeAway

    Great feel of a home away from home. You will enjoy a very clean and tidy house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Guests are sure to enjoy a memorable vacation in style with a fully furnished, 3 bedroom/2 bath, custom built home that ...

    From $100 per night (USD)

    HomeAway

    Details
  • W01 - 837 97th Street
    From $236 per night (USD)

    VRBO

    W01 - 837 97th Street

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Fantastic Ocean Side Pool Home on Easy Access Canal! This home has a seven night minimum. Newly updated 3 b ...

    From $236 per night (USD)

    VRBO

    Details
  • P00 - 500 Corte De Luna
    From $307 per night (USD)

    HomeAway

    P00 - 500 Corte De Luna

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    8

    This beautiful 4 bedroom, 3.5 bath family home is located in the very desirable area of Sombrero Beach. This spectacular ...

    From $307 per night (USD)

    HomeAway

    Details
  • TURTLE COVE ~ Located in Desirable Casa Marina District Minutes from Beach!
    From $680 per night (USD)

    VRBO

    "TURTLE COVE" ~ Located in Desirable Casa Marina District Minutes from Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A SWEET RETREAT MINUTES AWAY FROM THE BEACH… Perfect apartment located in Old Town in the desired Casa Marina District. ...

    From $680 per night (USD)

    VRBO

    Details
  • P50 - 208 S Anglers Dr
    From $314 per night (USD)

    HomeAway

    P50 - 208 S Anglers Dr

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    Enjoy the Florida Keys in this lovely 3 bedroom 2 bath canal home with a pool located minutes away from Sombrero Beach! ...

    From $314 per night (USD)

    HomeAway

    Details
  • Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
    From $157 per night (USD)

    VRBO

    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...

    From $157 per night (USD)

    VRBO

    Details
  • P01 - 130 Mockingbird
    From $307 per night (USD)

    HomeAway

    P01 - 130 Mockingbird

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    8

    Sun Lovers Paradise! If you are looking for a sun-filled oasis, look no further. This home is spectacular inside and out ...

    From $307 per night (USD)

    HomeAway

    Details
  • P11 - 111B Alynn in Marathon
    From $154 per night (USD)

    VRBO

    P11 - 111B Alynn in Marathon

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Canal Front in Marathon, Florida Escape to this luxurious paradise home designed for VIP guest. Relax and enjoy br ...

    From $154 per night (USD)

    VRBO

    Details
  • New Listing! Beautiful Canal front , Key Deer and jacuzzi.
    From $200 per night (USD)

    HomeAway

    New Listing! Beautiful Canal front , Key Deer and jacuzzi.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    -Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - B ...

    From $200 per night (USD)

    HomeAway

    Details
  • P78 - 497 Sombrero Beach Rd
    From $221 per night (USD)

    VRBO

    P78 - 497 Sombrero Beach Rd

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    This charming 3 bedroom, 2 bath single family home is ideally located in the heart of Sombrero Beach and is an easy 7 mi ...

    From $221 per night (USD)

    VRBO

    Details
  • P41 - 135 Unit 4D Coco Plum
    From $164 per night (USD)

    HomeAway

    P41 - 135 Unit 4D Coco Plum

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Off the beaten path Condo that overlooks the natural beach of Coco Plum. Enjoy unrestricted views of the beach and dail ...

    From $164 per night (USD)

    HomeAway

    Details
  • 28 night minimum Key West 'Coral Hammock' - Poolside - 36 with a shared pool
    From $300 per night (USD)

    VRBO

    28 night minimum Key West 'Coral Hammock' - Poolside - 36 with a shared pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This minimum 28 day rental is located Coral Hammock is one of Key West gated communities. The unit has three bedrooms an ...

    From $300 per night (USD)

    VRBO

    Details
  • Paradise Vacation For Rent
    From $100 per night (USD)

    HomeAway

    Paradise Vacation For Rent

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    One bedroom one bathroom mobile home located Oceanside on beautiful Windley key in Islamorada Florida keys the sport fi ...

    From $100 per night (USD)

    HomeAway

    Details
  • P53 - 11242 First Avenue Gulf
    From $221 per night (USD)

    VRBO

    P53 - 11242 First Avenue Gulf

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Rents by the Week, Jan. & March-Dec.; Rents by the Month Only in Feb. Beautifully Maintained Pool Home offering 3 ...

    From $221 per night (USD)

    VRBO

    Details
  • P42 - 37 Indigo Reef
    From $179 per night (USD)

    HomeAway

    P42 - 37 Indigo Reef

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Enjoy this brand new luxury gulf front townhouse in the beautiful gated community of Indigo Reef. This home featur ...

    From $179 per night (USD)

    HomeAway

    Details
  • P49 - 63 Tingler in Marathon
    From $193 per night (USD)

    VRBO

    P49 - 63 Tingler in Marathon

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    A Showplace with complete updating throughout, offering 2 bedrooms, 2 bathrooms. Just one block from Sombrero Beach. Spe ...

    From $193 per night (USD)

    VRBO

    Details
  • P05 - 295 14th St in Key Colony Beach
    From $736 per night (USD)

    HomeAway

    P05 - 295 14th St in Key Colony Beach

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    10

    This custom designed Mediterranean style home is nothing less than exquisite! Located in very desirable Key Colony Beach ...

    From $736 per night (USD)

    HomeAway

    Details
  • Waterview, ground floor condo with 32' boat slip in Buttonwood Bay
    From $100 per night (USD)

    VRBO

    Waterview, ground floor condo with 32' boat slip in Buttonwood Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy breezy shady mornings on the terrace overlooking the water and stunning sunsets a few steps away. Buttonwood Bay o ...

    From $100 per night (USD)

    VRBO

    Details
  • P21 - 541 8th Street
    From $179 per night (USD)

    HomeAway

    P21 - 541 8th Street

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    8

    This is a beautiful 3 bedroom 3.5 bath duplex. This Mediterranean style home offers 37 feet of deep water dockage, washe ...

    From $179 per night (USD)

    HomeAway

    Details
  • @@ New Ownerss many upgrades, Tropical retreat on the ocean@@
    From $240 per night (USD)

    VRBO

    @@ New Ownerss many upgrades, Tropical retreat on the ocean@@

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...

    From $240 per night (USD)

    VRBO

    Details
  • P72 - 200 10th St in Key Colony Beach
    From $207 per night (USD)

    HomeAway

    P72 - 200 10th St in Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    Beautiful duplex in Key Colony Beach. Each side features 4 bed/2 bath being able to house 8 occupants per side. Upon ent ...

    From $207 per night (USD)

    HomeAway

    Details
  • Gem By the Sea, Beautiful Condo in Moon Bay Key Largo
    From $245 per night (USD)

    VRBO

    Gem By the Sea, Beautiful Condo in Moon Bay Key Largo

    Bedrooms:
    2.5
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful 2 Bedroom, 1 1/2 bathroom Condo with den with futon, located in Moon Bay located in Key Largo. Property is l ...

    From $245 per night (USD)

    VRBO

    Details
  • P31 - 230 11th St, KCB
    From $156 per night (USD)

    HomeAway

    P31 - 230 11th St, KCB

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Luxury duplex offering 2 bedrooms, 2 bathrooms, spacious open design with great room, dining area and kitchen. The home ...

    From $156 per night (USD)

    HomeAway

    Details
  • P17 - 296 Sadowski in Key Colony Beach
    From $179 per night (USD)

    VRBO

    P17 - 296 Sadowski in Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Paradise found in the tropical city of Key Colony Beach! This property was completely remodeled in 2018, post Hurricane ...

    From $179 per night (USD)

    VRBO

    Details
  • P59 - 11340 6th Ave Ocean
    From $179 per night (USD)

    HomeAway

    P59 - 11340 6th Ave Ocean

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Charming 2 bedroom, 2 bath single family home on a beautiful Oceanside canal. This home has been completely updat ...

    From $179 per night (USD)

    HomeAway

    Details
  • BOOMERANG BOATHOUSE ~ Relax in This Beautiful 4 Bedroom/4 Bath Location!
    From $1295 per night (USD)

    VRBO

    "BOOMERANG BOATHOUSE" ~ Relax in This Beautiful 4 Bedroom/4 Bath Location!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    8

    RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows.  T ...

    From $1295 per night (USD)

    VRBO

    Details
  • Ocean Views in Paradise!  5308 Ocean Pointe Suites
    From $300 per night (USD)

    HomeAway

    Ocean Views in Paradise! 5308 Ocean Pointe Suites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    All new, fully renovated, pictures are up-to-date! We are excited to present to you this pristine and upgraded 2 bedr ...

    From $300 per night (USD)

    HomeAway

    Details
  • Sun Kissed Keys 2 bed 2.5 bath Condo with shared pool & first come dockage
    From $125 per night (USD)

    VRBO

    Sun Kissed Keys 2 bed 2.5 bath Condo with shared pool & first come dockage

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Seven Night Minimum NO EXCEPTIONS. Maximum Occupancy: 6 (NO MATTER THE AGE) This is a regulation set up by The City of ...

    From $125 per night (USD)

    VRBO

    Details
  • Pirate`s Den 3bed/2bath single family with dockage
    From $350 per night (USD)

    HomeAway

    Pirate`s Den 3bed/2bath single family with dockage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 8 (NO MATTER THE AGE) This regulation is set by The City of Marathon ...

    From $350 per night (USD)

    HomeAway

    Details
  • Tropical Bayfront Home
    From $200 per night (USD)

    VRBO

    Tropical Bayfront Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautiful property located on Tarpon Basin in Key Largo with 45 feet of frontage. Our house has two bedrooms and two ba ...

    From $200 per night (USD)

    VRBO

    Details
  • 3/2 canal front minutes to open ocean
    From $209 per night (USD)

    HomeAway

    3/2 canal front minutes to open ocean

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 3/2 newly renovated all new bathrooms and furnishings. 40’ canal frontage with ocean access 2 mintues from the ...

    From $209 per night (USD)

    HomeAway

    Details
  • P74 - 23 Kyle Way in Marathon
    From $321 per night (USD)

    VRBO

    P74 - 23 Kyle Way in Marathon

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    8

    This beautiful, waterfront home is located at the south end of Marathon, near the base of the Seven Mile Bridge, directl ...

    From $321 per night (USD)

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  • P5657 800 and 810 10th St, KCB
    From $428 per night (USD)

    HomeAway

    P5657 800 and 810 10th St, KCB

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    14

    Twin Dolphins at Shelter Bay Great duplex in the very desirable Key Colony Beach! This well-appointed 6 bedroom, 5 ...

    From $428 per night (USD)

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  • P58 - 58039 Morton St
    From $428 per night (USD)

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    P58 - 58039 Morton St

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    8

    Grassy Key, Florida, Waterfront home GULF FRONT - Newly Remodeled! Breathtaking views! Gulf water front. Thi ...

    From $428 per night (USD)

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  • Sunset View in Key Largo
    From $140 per night (USD)

    HomeAway

    Sunset View in Key Largo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Are you looking for a Brand new 2017 trailer with high sealing will make you feel at home A place where you can arrive, ...

    From $140 per night (USD)

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    Details
  • Big Kahuna 5bed/4bath Pool House
    From $550 per night (USD)

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    Big Kahuna 5bed/4bath Pool House

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    7 night minimum, NO EXCEPTIONS Max Occupancy: 12 (NO MATTER THE AGE) Per the city of Marathon's rule of 2 per bedroom pl ...

    From $550 per night (USD)

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    Details
  • MEMORY MAKER ~This Property Was Featured on HGTV's show Island Life!
    From $645 per night (USD)

    HomeAway

    "MEMORY MAKER" ~This Property Was Featured on HGTV's show "Island Life"!

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    A STYLISH CARIBBEAN SURPRISE RIGHT OFF DUVAL... Private single-family home with peaceful porches totaling two bedrooms, ...

    From $645 per night (USD)

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  • P13 - 280 13th Street
    From $264 per night (USD)

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    P13 - 280 13th Street

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    A premier home in a premier location! This 3 bedroom, 2 bathroom home is one of a kind. An all ground level home boastin ...

    From $264 per night (USD)

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  • Luxury Vacation Home by the Water in Beautiful Key Largo, only 1 hour from Miami
    From $225 per night (USD)

    HomeAway

    Luxury Vacation Home by the Water in Beautiful Key Largo, only 1 hour from Miami

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    House has been totally remodeled , inside and out . Property has 2 bedrooms and 2 bathrooms , air condition , fully stoc ...

    From $225 per night (USD)

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    Details
  • P12 - 1235 101St St Ocean
    From $500 per night (USD)

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    P12 - 1235 101St St Ocean

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    2018 brought this rare open water-front home a complete remodel and the results are fabulous! This 3 bedroom, 2.5 ...

    From $500 per night (USD)

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    Details
  • P26 - 295 13th Street, KCB
    From $264 per night (USD)

    HomeAway

    P26 - 295 13th Street, KCB

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This 3 bedroom, 2 bathroom home is gorgeous inside and out and is comfortably set in the highly desirable Key Colony Bea ...

    From $264 per night (USD)

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    Details
  • P33 - 333 Calzada de Boug
    From $350 per night (USD)

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    P33 - 333 Calzada de Boug

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    8

    Tropical Isle - 4 bedroom home in Sombrero Beach with a private pool and amazing views! Looking for the perfect va ...

    From $350 per night (USD)

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    Details
  • *Searenity Beach House*  - Ocean Front Home with Views of the Atlantic Ocean
    From $359 per night (USD)

    HomeAway

    *Searenity Beach House* - Ocean Front Home with Views of the Atlantic Ocean

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Beautiful home, facing ocean views indoors and out! The house affords breath taking views of the atlantic ocean, Snorke ...

    From $359 per night (USD)

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    Details
  • Stunningly decorated 2 bedroom 1.5 bath in coveted Plantation Key, Islamorada
    From $150 per night (USD)

    VRBO

    Stunningly decorated 2 bedroom 1.5 bath in coveted Plantation Key, Islamorada

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    5

    Beautifully updated and decorated 2 bedroom, 1.5 bath in the heart of Plantation Key, Islamorada – the fishing capital o ...

    From $150 per night (USD)

    VRBO

    Details
  • QUIESCENT 2BR CONDO W/ LUSH VIEWS
    From $150 per night (USD)

    HomeAway

    QUIESCENT 2BR CONDO W/ LUSH VIEWS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RELAX & RECHARGE OR PLAN YOUR FAMILIES NEXT GREAT ADVENTURE AT OUR QUAINT CONDO WITH LUSH MANGROVE AND OCEAN VIEWS NESTL ...

    From $150 per night (USD)

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  • Ocean Front Islamorada Retreat
    From $425 per night (USD)

    VRBO

    Ocean Front Islamorada Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Ocean Front Retreat: Come enjoy this wonderful relaxing 3 bedroom 2 bath newly renovated cozy home in the Village of Isl ...

    From $425 per night (USD)

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  • SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
    From $680 per night (USD)

    HomeAway

    "SEAPORT SANCTUARY" ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town.  A great place for a coup ...

    From $680 per night (USD)

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  • M18 -1998 Overseas Highway A23
    From $150 per night (USD)

    VRBO

    M18 -1998 Overseas Highway A23

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Spacious 3 bedroom 2 bathroom, second floor unit, with split floor plan. Lounge on the large screened wrap aroun ...

    From $150 per night (USD)

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    Details
  • Beautiful 1 bedroom apartment with a Phenomenal direct bay view 312
    From $150 per night (USD)

    HomeAway

    Beautiful 1 bedroom apartment with a Phenomenal direct bay view 312

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This apartment has a million dollar view, the kind you have always dreamed of for a vacation of a lifetime! The apartmen ...

    From $150 per night (USD)

    HomeAway

    Details
  • Beautiful 2 bedroom upstairs home in Islamorada
    From $159 per night (USD)

    VRBO

    Beautiful 2 bedroom upstairs home in Islamorada

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    You'll love it here! The house is on a canal lot that's right off Tavernier Creek in a quiet neighborhood that's close t ...

    From $159 per night (USD)

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    Details
  • P76 - 401 Sombrero Beach Road
    From $321 per night (USD)

    HomeAway

    P76 - 401 Sombrero Beach Road

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    This desirable Sombrero area pool home just a short walk to Sombrero Beach. There is a pathway leading from the front th ...

    From $321 per night (USD)

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    Details
  • Angler`s Dream 2bed 2bath Duplex w/pool & dockage
    From $150 per night (USD)

    VRBO

    Angler`s Dream 2bed 2bath Duplex w/pool & dockage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 6 (NO MATTER THE AGE) This regulation is set by The City of Marathon ...

    From $150 per night (USD)

    VRBO

    Details
  • SPARROW'S LANDING ~ Casual Sophistication Located in a Quiet Neighborhood!
    From $1095 per night (USD)

    HomeAway

    "SPARROW'S LANDING" ~ Casual Sophistication Located in a Quiet Neighborhood!

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    STEP INTO PARADISE... Located in the peaceful neighborhood locals call The Meadows, this home is set away from the noise ...

    From $1095 per night (USD)

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    Details
  • SUGAR SHACK ~ 3 Bed/3 Bath Pet Friendly Townhome in Gated Community!
    From $250 per night (USD)

    VRBO

    "SUGAR SHACK" ~ 3 Bed/3 Bath Pet Friendly Townhome in Gated Community!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    PERFECT FAMILY RETREAT IN LUSH GATED COMMUNITY Enjoy this incredible family townhome in Coral Hammock’s lush community j ...

    From $250 per night (USD)

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    Details
  • CAPT JACK'S HIDEAWAY ~ Vintage Conch Cottage Located on a Quiet Lane!
    From $745 per night (USD)

    HomeAway

    "CAPT JACK'S HIDEAWAY" ~ Vintage Conch Cottage Located on a Quiet Lane!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    QUIET LOCATION, COMFORTABLE SPACE… Located in Old Town, this home sits on a quaint little lane.  With limited homes on t ...

    From $745 per night (USD)

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    Details
  • LUNA VERDE ~ 3 Bedroom, 2 Bath in a Quiet Neighborhood Near the Beach!
    From $745 per night (USD)

    VRBO

    "LUNA VERDE" ~ 3 Bedroom, 2 Bath in a Quiet Neighborhood Near the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    LUNA VERDE... This home is nicely situated in a quiet neighborhood just a few shorts blocks from Higgs Beach and White S ...

    From $745 per night (USD)

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    Details
  • MARGAUX'S HIDEAWAY~ Extraordinary, luxury home in Old Town Key West!
    From $1445 per night (USD)

    HomeAway

    "MARGAUX'S HIDEAWAY"~ Extraordinary, luxury home in Old Town Key West!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    ESCAPE TO THIS PEACEFUL PARADISE... "Margaux's Hideaway", is a luxury vacation rental named for its ties to the famous a ...

    From $1445 per night (USD)

    HomeAway

    Details
  • THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
    From $250 per night (USD)

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    "THE OLD SAPODILLA HOUSE" ~ Pet Friendly Home in Historic Bahama Village

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...

    From $250 per night (USD)

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    Details
  • MOJITO DREAMIN ~ Pet Friendly 3B/3Ba Condo Near Golf Course and Restaurants
    From $250 per night (USD)

    HomeAway

    "MOJITO DREAMIN" ~ Pet Friendly 3B/3Ba Condo Near Golf Course and Restaurants

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    WELL MANICURED COMMUNITY, SHORT DISTANCE FROM KEY WEST… Enjoy this modern, coastal inspired townhome that reflects the l ...

    From $250 per night (USD)

    HomeAway

    Details
  • ISLAND TIME ~ Fully Renovated Conch Home in a Great Old Town Location!
    From $550 per night (USD)

    VRBO

    "ISLAND TIME" ~ Fully Renovated Conch Home in a Great Old Town Location!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    EASE INTO ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pas ...

    From $550 per night (USD)

    VRBO

    Details
  • A Secluded Key Largo Retreat- An Hour From Miami, But World's Away.
    From $117 per night (USD)

    HomeAway

    A Secluded Key Largo Retreat- An Hour From Miami, But World's Away.

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    Available for three month minimum, the Sanctuary is a unique condo development that lives up to its name. A private gate ...

    From $117 per night (USD)

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    Details
  • Home Away From Home Keys Paradise Rental
    From $225 per night (USD)

    VRBO

    Home Away From Home Keys Paradise Rental

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Stay in a 2/1 trailer with washer and dryer. Master bedroom has queen and other bedroom has a twin bed with trundle, sle ...

    From $225 per night (USD)

    VRBO

    Details
  • P03 - 98 Ave E in Marathon
    From $321 per night (USD)

    HomeAway

    P03 - 98 Ave E in Marathon

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    10

    Spring of 2018 brought this home a complete remodel and the results are stunning! This beautiful home is located ...

    From $321 per night (USD)

    HomeAway

    Details
  • Harbor House 2bed 2bath Open water views & dockage
    From $125 per night (USD)

    VRBO

    Harbor House 2bed 2bath Open water views & dockage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 4 (NO MATTER THE AGE) This regulation is set by The City of Marathon ...

    From $125 per night (USD)

    VRBO

    Details
  • No Hurricane Damage 132 Anglers Reef Monthly Rental- new to rental pool  DOCK
    From $759 per night (USD)

    HomeAway

    No Hurricane Damage 132 Anglers Reef Monthly Rental- new to rental pool DOCK

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Please call me with questions. 305 . 240 . 0592 Anglers Reef had no substantial damage or flooding to the homes. They ...

    From $759 per night (USD)

    HomeAway

    Details
  • SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
    From $350 per night (USD)

    VRBO

    "SEAS THE DAY"~ Newly Built Townhome in Perfect Location with Community Pool!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...

    From $350 per night (USD)

    VRBO

    Details
  • Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
    From $164 per night (USD)

    HomeAway

    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...

    From $164 per night (USD)

    HomeAway

    Details
  • Latitude Adjustment 2bed/2bath UPDATED Duplex
    From $330 per night (USD)

    VRBO

    Latitude Adjustment 2bed/2bath UPDATED Duplex

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    SEVEN NIGHT MINIMUM (NO EXCEPETIONS) MAX OCCUPANCY: 4 (THIS RULE IS PER KEY COLONY’S RULE OF 1 PERSON PER 200 SQFT – NO ...

    From $330 per night (USD)

    VRBO

    Details
  • Quiet and Serene - Deep Water Oceanside 
30 Day Minimum Rental
    From $300 per night (USD)

    HomeAway

    Quiet and Serene - Deep Water Oceanside 30 Day Minimum Rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    kayak at house for guests use . Private two bedroom, two bath on beautiful little torch key (ocean side) on wooded c ...

    From $300 per night (USD)

    HomeAway

    Details
  • Hearts & Palms House-Quaint 3BD/3Bath Monthly Home Rental - Private Pool
    From $205 per night (USD)

    VRBO

    Hearts & Palms House-Quaint 3BD/3Bath Monthly Home Rental - Private Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    WELCOME TO HEARTS & PALMS HOUSE! We are complying with the directives listed on the Monroe County website. Please be ...

    From $205 per night (USD)

    VRBO

    Details
  • Beautiful Sunsets in Key Largo House 2br 1 bth
    From $200 per night (USD)

    HomeAway

    Beautiful Sunsets in Key Largo House 2br 1 bth

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    **3 Miles from John Pennekamp State Park! **Snorkeling/Dive charter right outside our neighborhood! Looking to vacatio ...

    From $200 per night (USD)

    HomeAway

    Details
  • Florida Keys Paradise
    From $350 per night (USD)

    VRBO

    Florida Keys Paradise

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    6

    Spacious vacation home on the water in the beautiful Florida Keys. Fully furnished with all amenities and many recreatio ...

    From $350 per night (USD)

    VRBO

    Details
  •  2 bedroom 2.5 bath town home in Old town Key West- Monthly Rental only
    From $200 per night (USD)

    HomeAway

    2 bedroom 2.5 bath town home in Old town Key West- Monthly Rental only

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    A CUT ABOVE II in OLD TOWN-PARK@YOUR DOOR Even though this is a 29 day rental-you can get together with friends or famil ...

    From $200 per night (USD)

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    Details
  • SEA LA VIE ~Living in Complete Luxury in This Elegant Three Story Home!
    From $1455 per night (USD)

    VRBO

    "SEA LA VIE" ~Living in Complete Luxury in This Elegant Three Story Home!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    THREE STORY GRANDEUR… Located in the Casa Marina District in Old Town.  This home is elegant, yet quite the tropical del ...

    From $1455 per night (USD)

    VRBO

    Details
  • THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
    From $1195 per night (USD)

    HomeAway

    "THE SEASHELL" ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    CLASSIC KEY When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dr ...

    From $1195 per night (USD)

    HomeAway

    Details
  • Key West-Coconut Beach Resort - Avail 11/14/20 to 11/21/20
    From $59 per night (USD)

    VRBO

    Key West-Coconut Beach Resort - Avail 11/14/20 to 11/21/20

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Book it before it's gone! 7 day rental - available from Saturday 11/14/20 to Saturday 11/21/20 only. Cozy and comforta ...

    From $59 per night (USD)

    VRBO

    Details
  • Spanish Galleon 2bed/2bath open water view condo with shared pool
    From $150 per night (USD)

    HomeAway

    Spanish Galleon 2bed/2bath open water view condo with shared pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    NEW PICTURES COMING SOON! UPDATED 2 bed 2 bath condo that over looks beautiful Boot Key Harbor! Enjoy watching beautiful ...

    From $150 per night (USD)

    HomeAway

    Details
  • Oceanfront Sunsets in the Florida Keys
    From $190 per night (USD)

    VRBO

    Oceanfront Sunsets in the Florida Keys

    Bedrooms:
    7
    Bathrooms:
    4
    Sleeps:
    8

    FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...

    From $190 per night (USD)

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    Details
  • P22 - 270 Sadowski in Key Colony Beach
    From $179 per night (USD)

    HomeAway

    P22 - 270 Sadowski in Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    7

    CANAL FRONT Beautiful duplex in Key Colony Beach with private fenced yard and private heat optional pool. Three b ...

    From $179 per night (USD)

    HomeAway

    Details
  • Great Yearly Rental at 1800 Atlantic next available May 2021
    From $125 per night (USD)

    VRBO

    Great Yearly Rental at 1800 Atlantic next available May 2021

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...

    From $125 per night (USD)

    VRBO

    Details
  • BEACH HOUSE~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
    From $300 per night (USD)

    HomeAway

    "BEACH HOUSE"~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...

    From $300 per night (USD)

    HomeAway

    Details
  • BLUE ROOSTER ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!
    From $1445 per night (USD)

    VRBO

    "BLUE ROOSTER" ~ Spectacular 4 Bed/4 Bath with Pool and Solarium in Old Town!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    OLD TOWN Paradise awaits in a quiet Old Town location.  This four bedroom home is set on a cozy lane that is off the be ...

    From $1445 per night (USD)

    VRBO

    Details
  • Sunset Ocean Views In Key Largo - Florida
    From $226 per night (CAD)

    HomeAway

    Sunset Ocean Views In Key Largo - Florida

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the panoramic view this tropically decorated, fifth-story penthouse unit has to offer of the Atlantic Ocean and th ...

    From $226 per night (CAD)

    HomeAway

    Details
  • Closer to Cuba than Walmart - Blu
    From $150 per night (USD)

    VRBO

    Closer to Cuba than Walmart - Blu

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This nightly rental i ...

    From $150 per night (USD)

    VRBO

    Details
  • NEW & BEAUTIFUL HOME WATERFRONT WITH HEATED POOL AND FULL OUTDOOR KITCHEN
    From $200 per night (USD)

    HomeAway

    NEW & BEAUTIFUL HOME WATERFRONT WITH HEATED POOL AND FULL OUTDOOR KITCHEN

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Home is located just south of John Pennekamp Park. Direct ocean access. Very clean canal that you can enjoy kayaking and ...

    From $200 per night (USD)

    HomeAway

    Details
  • CONNIE'S COTTAGE - Old-world charm and elegant tropical living
    From $150 per night (USD)

    VRBO

    CONNIE'S COTTAGE - Old-world charm and elegant tropical living

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    28 Day minimum Rental: Old-world charm and elegant tropical living are waiting for you in this classic old town conch h ...

    From $150 per night (USD)

    VRBO

    Details
  • Pink Flamingo 2bed/3bath Condo with Pool
    From $175 per night (USD)

    HomeAway

    Pink Flamingo 2bed/3bath Condo with Pool

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Seven Night Minimum, NO EXCEPTIONS. This condominium at The Reef in Marathon, Middle Keys is a true resort setting with ...

    From $175 per night (USD)

    HomeAway

    Details
  • Bring your Flip-Flops to this spacious tranquil home on a canal and bay view.
    From $125 per night (USD)

    VRBO

    Bring your Flip-Flops to this spacious tranquil home on a canal and bay view.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bring your sandals!!! Tucked at the turn of a spacious waterway is this tranquil and relaxing home just perfect for anyo ...

    From $125 per night (USD)

    VRBO

    Details
  • Paradise - updated Key Largo Waterfront home with Dock
    From $160 per night (USD)

    HomeAway

    Paradise - updated Key Largo Waterfront home with Dock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Make our Home your Vacation destination Don't miss out on this recently updated lovely 2 bedroom 2 bath, waterfront, poo ...

    From $160 per night (USD)

    HomeAway

    Details
  • SERENITY ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!
    From $1145 per night (USD)

    VRBO

    "SERENITY" ~ Relax in Ultimate Luxury and Comfort in Old Town Key West!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    LOCAL Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  3 bedroom home, with 3 ...

    From $1145 per night (USD)

    VRBO

    Details
  • Super Grouper - new, lux 5BR 7BA house with pool and dock
    From $428 per night (USD)

    HomeAway

    Super Grouper - new, lux 5BR 7BA house with pool and dock

    Bedrooms:
    7.5
    Bathrooms:
    5
    Sleeps:
    10

    Watch the game from the pool, read a good book in the daybed, take a quiet and private nap in the shaded hammock or spla ...

    From $428 per night (USD)

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    Details
  • Buttonwood Bay - Fully Remodeled - Boat Slip Available
    From $167 per night (USD)

    VRBO

    Buttonwood Bay - Fully Remodeled - Boat Slip Available

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Located in the beautiful gated community of Buttonwood Bay, this unit has been completely remodeled with no expenses spa ...

    From $167 per night (USD)

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    Details
  • Beautiful 2 bedroom 2.5 bath Condo on the water in upscale rental resort
    From $279 per night (USD)

    HomeAway

    Beautiful 2 bedroom 2.5 bath Condo on the water in upscale rental resort

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy the best, quiet condo in the Mariners Club community. The unit is a luxurious 2/2.5 condo on the oceanside are in ...

    From $279 per night (USD)

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    Details
  • 2 Bedroom 2 1/2 Bath Condo in Key Largo, FL with Boat Slip! Sept 2021
    From $75 per night (USD)

    VRBO

    2 Bedroom 2 1/2 Bath Condo in Key Largo, FL with Boat Slip! Sept 2021

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    2 Bedroom 2 1/2 Bath Condo in Key Largo, Florida with your own boat slip and Water Views from Balconies. Book for Augus ...

    From $75 per night (USD)

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    Details
  • Luxurious Keywest resort condominium unit
    From $184 per night (USD)

    HomeAway

    Luxurious Keywest resort condominium unit

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located in the Hyatt Windward Pointe and affords beautiful Atlantic Ocean views. This unit has two-bedrooms, 1 is a mast ...

    From $184 per night (USD)

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    Details
  • Quaint Old Town Key West Cottage with Heated  Pool and Private Parking
    From $140 per night (USD)

    VRBO

    Quaint Old Town Key West Cottage with Heated Pool and Private Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Conch Escape is a 2 bedroom 2 bath cottage situated in a private gated compound of ten homes in Old Town Key West. Thes ...

    From $140 per night (USD)

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    Details
  • Key Largo Condo--A bit of Tropical Paradise
    From $100 per night (USD)

    HomeAway

    Key Largo Condo--A bit of Tropical Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Swim, bike, boat, jog, walk or just relax and enjoy a little bit of paradise in our tropical setting at the gated commun ...

    From $100 per night (USD)

    HomeAway

    Details
  • SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
    From $995 per night (USD)

    VRBO

    "SEAHORSE COVE" ~ Tropical Luxury Located In The Heart Of Old Town Key West!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...

    From $995 per night (USD)

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    Details
  • Oceanfront Resort ~ Breathtaking Sunrise *
    From $399 per night (USD)

    HomeAway

    Oceanfront Resort ~ Breathtaking Sunrise *

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Ocean Pointe Suites! Come unwind in one of our tropically inspired one bedroom fully equipped suites. We ar ...

    From $399 per night (USD)

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    Details
  • Charming and Private
    From $190 per night (USD)

    VRBO

    Charming and Private

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    20 Miles from Key West and mini golf, private pool & hot tub, deluxe outdoor kitchen, outdoor shower, screened in porch ...

    From $190 per night (USD)

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    Details
  • Waterfront Slice of Paradise in the Florida Keys
    From $200 per night (USD)

    HomeAway

    Waterfront Slice of Paradise in the Florida Keys

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Bring your boat to this waterfront property in prestigious Venetian Shores. Get away to this perfectly situated 3 bedro ...

    From $200 per night (USD)

    HomeAway

    Details
  • LET THE SUN SHINE - 3/2 Tavernier Home Near Snake Creek Marina and Shopping
    From $159 per night (USD)

    VRBO

    LET THE SUN SHINE - 3/2 Tavernier Home Near Snake Creek Marina and Shopping

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Discover a tropical retreat at this Tavernier vacation spot. Boasting everything you'll need for the ideal Florida Keys ...

    From $159 per night (USD)

    VRBO

    Details
  • P64 - 260 4th Street
    From $171 per night (USD)

    HomeAway

    P64 - 260 4th Street

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    8

    Beautiful Bungalow Duplex in Key Colony Beach! Delight in this island paradise where the weather is beautiful year round ...

    From $171 per night (USD)

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    Details
  • P69 - 669 Corte Del Brisas
    From $321 per night (USD)

    VRBO

    P69 - 669 Corte Del Brisas

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    10

    Spring of 2019 brought this home a complete remodel and the results are fabulous! This home is located in the very ...

    From $321 per night (USD)

    VRBO

    Details
  • W04 - 209 Sombrero Beach
    From $286 per night (USD)

    HomeAway

    W04 - 209 Sombrero Beach

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This home is a Saturday through Saturday vacation rental during peak weeks with a seven night minimum. Newer buil ...

    From $286 per night (USD)

    HomeAway

    Details
  • P60 - 201 East Bruce Court
    From $285 per night (USD)

    VRBO

    P60 - 201 East Bruce Court

    Bedrooms:
    4
    Bathrooms:
    1
    Sleeps:
    10

    Fresh and fabulous best describe this newest addition to our gorgeous gulf side community! This brand new home, a ...

    From $285 per night (USD)

    VRBO

    Details
  • W07 - 2390 Coco Plum Dr Unit 1
    From $714 per night (USD)

    HomeAway

    W07 - 2390 Coco Plum Dr Unit 1

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Brand new construction built in 2019. Be one of the first to stay in this luxury home. 6 Bedrooms 6.5 Bathro ...

    From $714 per night (USD)

    HomeAway

    Details
  • W09 - 2394 Coco Plum Dr Unit 3
    From $714 per night (USD)

    VRBO

    W09 - 2394 Coco Plum Dr Unit 3

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Brand new construction built in 2019. Be one of the first to stay in this luxury home. 6 Bedrooms 6.5 Bathro ...

    From $714 per night (USD)

    VRBO

    Details
  • W08 - 2394 Coco Plum Dr Unit 2
    From $714 per night (USD)

    HomeAway

    W08 - 2394 Coco Plum Dr Unit 2

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    Brand new construction built in 2019. Be one of the first to stay in this luxury home. 6 Bedrooms 6.5 Bathro ...

    From $714 per night (USD)

    HomeAway

    Details
  • W05 - 122 W Bruce Court
    From $139 per night (USD)

    VRBO

    W05 - 122 W Bruce Court

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Light and bright canal front home on the Gulf. Plenty of dockage and fantastic views. 2 bedroom, 2 bath home with tropic ...

    From $139 per night (USD)

    VRBO

    Details
  • Tropical Breeze & Sunsets Moon Bay Town Home
    From $100 per night (USD)

    HomeAway

    Tropical Breeze & Sunsets Moon Bay Town Home

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This boutique condo townhouse is kept in pristine condition and has everything you will need to make your stay feel lik ...

    From $100 per night (USD)

    HomeAway

    Details
  • Fishing Capital of the World
    From $159 per night (USD)

    VRBO

    Fishing Capital of the World

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    2450sf split level home in the heart of the Florida Keys. This home has 60' of PRIVATE deep water dockage 100 yards from ...

    From $159 per night (USD)

    VRBO

    Details
  • Social distance, work remote (or not at all) in paradise at this beachy condo!
    From $150 per night (USD)

    HomeAway

    Social distance, work remote (or not at all) in paradise at this beachy condo!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Very flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, ...

    From $150 per night (USD)

    HomeAway

    Details
  • Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car,  Great Value!
    From $300 per night (USD)

    VRBO

    Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private b ...

    From $300 per night (USD)

    VRBO

    Details
  • Key Largo Vacation Paradise-KAWAMA TOWER
    From $400 per night (USD)

    HomeAway

    Key Largo Vacation Paradise-KAWAMA TOWER

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Keys are open and my condo is available for Short Term Rental. In Addition to Noted Enhanced Cleaning Procedures, UV ...

    From $400 per night (USD)

    HomeAway

    Details
  • 2 Incredible Waterfront Homes - One Low Price!
    From $375 per night (USD)

    VRBO

    2 Incredible Waterfront Homes - One Low Price!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Full Duplex with two 2-bedroom, 2-bath homes both with unobstructed view of the Gulf of Mexico. This is a great property ...

    From $375 per night (USD)

    VRBO

    Details
  • Newly redone condo with spectacular 5th floor open bay view.
    From $173 per night (USD)

    HomeAway

    Newly redone condo with spectacular 5th floor open bay view.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Clean and newly refurbished condo, with very nice accommodations. 2 Bedrooms with 2 bathroom/Showers, and also murphy be ...

    From $173 per night (USD)

    HomeAway

    Details
  • Rum And Coconuts - Coastal Living Boater's Paradise
    From $209 per night (USD)

    VRBO

    Rum And Coconuts - Coastal Living Boater's Paradise

    Bedrooms:
    2.5
    Bathrooms:
    4
    Sleeps:
    6

    Ocean access through Tavernier Creek is minutes away. Direct bay access for sunset cruises and backcountry fishing. 2 Be ...

    From $209 per night (USD)

    VRBO

    Details
  •  Eddie Griffiths Overnight Charters and  Vacation Rentals!!!!!
    From $25 per night (USD)

    HomeAway

    Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Its a custom built 43 ft sport fish made for overnight trips with all the comforts of home. Sleeps six and is kept in to ...

    From $25 per night (USD)

    HomeAway

    Details
  • Florida Keys Gem with Impressive Views
    From $150 per night (USD)

    VRBO

    Florida Keys Gem with Impressive Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Great renovated 1 bdrm condo with view of Boot Key Harbor. Relax on the balcony and watch the boats go by or sit on fron ...

    From $150 per night (USD)

    VRBO

    Details
  • Absolutely Stunning 4 Bedroom, 4 Bath Pool Home With Excellent Boating!!
    From $250 per night (USD)

    HomeAway

    Absolutely Stunning 4 Bedroom, 4 Bath Pool Home With Excellent Boating!!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Spectacular Ocean Front Estate located on beautiful Summerland Key!! This large 4 bedroom 4 bath home with heated pool h ...

    From $250 per night (USD)

    HomeAway

    Details
  • New Renovation - Condo in KCB Ocean Front Complex, Private Beach - 3 night min
    From $141 per night (USD)

    VRBO

    New Renovation - Condo in KCB Ocean Front Complex, Private Beach - 3 night min

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Everything is newly renovated in this gorgeous private studio condo that sleeps 2 people. Kitchen is all new with modern ...

    From $141 per night (USD)

    VRBO

    Details
  • One bedroom, one bath in Old Town with off street parking- Monthly Rental
    From $200 per night (USD)

    HomeAway

    One bedroom, one bath in Old Town with off street parking- Monthly Rental

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in the White Street Gallery district, this beautiful, recently-renovated 1.5 bedroom, one bathroom condo is perf ...

    From $200 per night (USD)

    HomeAway

    Details