Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 767 Rentals

  • Bayview House Apt 2
    From $90 per night (USD)

    VRBO

    Bayview House Apt 2

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...

    From $90 per night (USD)

    VRBO

    Details
  • A Sunset View
    From $207 per night (USD)

    VRBO

    A Sunset View

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $207 per night (USD)

    VRBO

    Details
  • MOJITO DREAMIN~Coastal Flair!
    From $250 per night (USD)

    VRBO

    "MOJITO DREAMIN"~Coastal Flair!

    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)

    VRBO

    Details
  • Frost Free at 1800 Atlantic Cayo Hueso C439
    From $288 per night (USD)

    VRBO

    Frost Free at 1800 Atlantic Cayo Hueso C439

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    1800 Atlantic Condominiums Unit C439 Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, two bath pent ...

    From $288 per night (USD)

    VRBO

    Details
  • MANGO MARGARITA~ Hideaway!
    From $395 per night (USD)

    VRBO

    "MANGO MARGARITA"~ Hideaway!

    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)

    VRBO

    Details
  • SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)
    From $480 per night (USD)

    VRBO

    SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST HARBOR, SUNSET KE ...

    From $480 per night (USD)

    VRBO

    Details
  • Captain's Daughter
    From $749 per night (USD)

    VRBO

    Captain's Daughter

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    "Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...

    From $749 per night (USD)

    VRBO

    Details
  • Paris Mango
    From $321 per night (USD)

    VRBO

    Paris Mango

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...

    From $321 per night (USD)

    VRBO

    Details
  • Seaside Retreat
    From $250 per night (USD)

    VRBO

    Seaside Retreat

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...

    From $250 per night (USD)

    VRBO

    Details
  • Tropical Paradise Key West A113
    From $240 per night (USD)

    VRBO

    Tropical Paradise Key West A113

    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
  • Pelican Landing St. Thomas Penthouse
    From $500 per night (USD)

    VRBO

    Pelican Landing St. Thomas Penthouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $500 per night (USD)

    VRBO

    Details
  • Jungle Breeze
    From $168 per night (USD)

    VRBO

    Jungle Breeze

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Jungle Breeze condo at LaBrisa Condominiums. *Ocean View *Free WiFi * Free Covered Parking * Final cleaning included ...

    From $168 per night (USD)

    VRBO

    Details
  • BLUE ROOSTER ~ Paradise!
    From $1445 per night (USD)

    VRBO

    "BLUE ROOSTER" ~ Paradise!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

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

    From $1445 per night (USD)

    VRBO

    Details
  • Island Time @ the Truman Annex
    From $207 per night (USD)

    VRBO

    Island Time @ the Truman Annex

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...

    From $207 per night (USD)

    VRBO

    Details
  • Octopus's Garden
    From $240 per night (USD)

    VRBO

    Octopus's Garden

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! OCTOPUS'S GAR ...

    From $240 per night (USD)

    VRBO

    Details
  • Nautical Wheeler
    From $250 per night (USD)

    VRBO

    Nautical Wheeler

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...

    From $250 per night (USD)

    VRBO

    Details
  • Aqua Oasis
    From $207 per night (USD)

    VRBO

    Aqua Oasis

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $207 per night (USD)

    VRBO

    Details
  • Splish Splash
    From $100 per night (USD)

    VRBO

    Splish Splash

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This jewel-li ...

    From $100 per night (USD)

    VRBO

    Details
  • Heavenly Hideaway
    From $205 per night (USD)

    VRBO

    Heavenly Hideaway

    Bedrooms:
    2.5
    Bathrooms:
    3
    Sleeps:
    6

    HEAVENLY HIDEAWAY! We are complying with the directives listed on the Monroe County website. Please be aware that info ...

    From $205 per night (USD)

    VRBO

    Details
  • Key West Beach Luxury Rental
    From $319 per night (USD)

    VRBO

    Key West Beach Luxury Rental

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all thr ...

    From $319 per night (USD)

    VRBO

    Details
  • Key West Suites Hotel #205
    Click For Pricing

    VRBO

    Key West Suites Hotel #205

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...

    Click For Pricing

    VRBO

    Details
  • ISLAND TIME ~ Conch Charm!
    From $550 per night (USD)

    VRBO

    "ISLAND TIME" ~ Conch Charm!

    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
  • Bimini  Key West Penthouse C424
    From $288 per night (USD)

    VRBO

    Bimini Key West Penthouse C424

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility Brand new living room furniture ...

    From $288 per night (USD)

    VRBO

    Details
  • Marlin Blue
    From $171 per night (USD)

    VRBO

    Marlin Blue

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...

    From $171 per night (USD)

    VRBO

    Details
  • Ocean Hideaway on the Atlantic A206
    From $270 per night (USD)

    VRBO

    Ocean Hideaway on the Atlantic A206

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Where the Ocean Meets the Windswept is nothing like . You don't have to spend a fortune to enjoy a spacious, clean and ...

    From $270 per night (USD)

    VRBO

    Details
  • A Sunrise Cottage
    From $279 per night (USD)

    VRBO

    A Sunrise Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...

    From $279 per night (USD)

    VRBO

    Details
  • Darling of Duval
    From $409 per night (USD)

    VRBO

    Darling of Duval

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Don't miss an ...

    From $409 per night (USD)

    VRBO

    Details
  • Susan's Key West Condo
    From $140 per night (USD)

    VRBO

    Susan's Key West Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...

    From $140 per night (USD)

    VRBO

    Details
  • Swept Away
    From $394 per night (USD)

    VRBO

    Swept Away

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SWEPT AWAY is ...

    From $394 per night (USD)

    VRBO

    Details
  • Seafarer's Refuge
    From $599 per night (USD)

    VRBO

    Seafarer's Refuge

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    10

    "Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...

    From $599 per night (USD)

    VRBO

    Details
  • Anchor Drop Key West A307
    From $300 per night (USD)

    VRBO

    Anchor Drop Key West A307

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...

    From $300 per night (USD)

    VRBO

    Details
  • Bohemian Rhapsody
    From $195 per night (USD)

    VRBO

    Bohemian Rhapsody

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! You might ask ...

    From $195 per night (USD)

    VRBO

    Details
  • Summer Solstice
    From $1522 per night (USD)

    VRBO

    Summer Solstice

    Bedrooms:
    10.5
    Bathrooms:
    9
    Sleeps:
    22

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! In Key West, ...

    From $1522 per night (USD)

    VRBO

    Details
  • Maison Tropicale
    From $683 per night (USD)

    VRBO

    Maison Tropicale

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Imagine a tra ...

    From $683 per night (USD)

    VRBO

    Details
  • CAPTAIN'S QUARTERS ~ A Gem!
    From $495 per night (USD)

    VRBO

    "CAPTAIN'S QUARTERS" ~ A Gem!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    10

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

    From $495 per night (USD)

    VRBO

    Details
  • Island Chic
    From $524 per night (USD)

    VRBO

    Island Chic

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...

    From $524 per night (USD)

    VRBO

    Details
  • Galleon Resort
    From $393 per night (USD)

    VRBO

    Galleon Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...

    From $393 per night (USD)

    VRBO

    Details
  • Sunset Point
    From $223 per night (USD)

    VRBO

    Sunset Point

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SUNSET POINT ...

    From $223 per night (USD)

    VRBO

    Details
  • STUDIO ROYALE - Welcome Pets
    From $309 per night (USD)

    VRBO

    STUDIO ROYALE - Welcome Pets

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Welcome to charming Studio Royale, a monthly Vacation Rental located in quirky Old Town Key West. Heated in ground pool. ...

    From $309 per night (USD)

    VRBO

    Details
  • My Florida Escape
    From $125 per night (USD)

    VRBO

    My Florida Escape

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...

    From $125 per night (USD)

    VRBO

    Details
  • Follow the Sun
    From $218 per night (USD)

    VRBO

    Follow the Sun

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! FOLLOW THE SU ...

    From $218 per night (USD)

    VRBO

    Details
  • Southernmost Hospitality VII
    From $981 per night (USD)

    VRBO

    Southernmost Hospitality VII

    Bedrooms:
    8.5
    Bathrooms:
    7
    Sleeps:
    16

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SOUTHERNMOST ...

    From $981 per night (USD)

    VRBO

    Details
  • Villa Mer at Shipyard Condominiums
    Click For Pricing

    VRBO

    Villa Mer at Shipyard Condominiums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...

    Click For Pricing

    VRBO

    Details
  • Paradise Found Cayo Hueso A111
    From $240 per night (USD)

    VRBO

    Paradise Found Cayo Hueso A111

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a ...

    From $240 per night (USD)

    VRBO

    Details
  • Bayview House Apt 1
    From $90 per night (USD)

    VRBO

    Bayview House Apt 1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...

    From $90 per night (USD)

    VRBO

    Details
  • Coconut Beach Resort
    From $243 per night (USD)

    VRBO

    Coconut Beach Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    PLEASE READ CAREFULLY BEFORE YOU EMAIL OWNER This is a Timeshare and I only own 1 week. This rental is for a FULL WEEK ...

    From $243 per night (USD)

    VRBO

    Details
  • Layover In Paradise
    From $218 per night (USD)

    VRBO

    Layover In Paradise

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! A home design ...

    From $218 per night (USD)

    VRBO

    Details
  • THE OLD SAPODILLA HOUSE~Peaceful!
    From $250 per night (USD)

    VRBO

    "THE OLD SAPODILLA HOUSE"~Peaceful!

    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)

    VRBO

    Details
  • Key West's Crown Jewel
    From $374 per night (USD)

    VRBO

    Key West's Crown Jewel

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We know that you will enjoy staying in this little piece of this island Paradise - Key West's Crown Jewel. This is a tw ...

    From $374 per night (USD)

    VRBO

    Details
  • Southern Comfort
    From $357 per night (USD)

    VRBO

    Southern Comfort

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...

    From $357 per night (USD)

    VRBO

    Details
  • Turtle Cay Island Delight C327
    From $240 per night (USD)

    VRBO

    Turtle Cay Island Delight C327

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fabulous 2 bedroom island view condominium, fully equipped unit. Full kitchen and washer dryer. There is a king in the m ...

    From $240 per night (USD)

    VRBO

    Details
  • **True Love Key West**
    Click For Pricing

    VRBO

    **True Love Key West**

    Bedrooms:
    6
    Bathrooms:
    3
    Sleeps:
    8

    **28-NIGHT MINIMUM PER CITY OF KEY WEST ORDINANCES** Fall in love with Key West while staying in our newly remodeled, g ...

    Click For Pricing

    VRBO

    Details
  • Jasmine Place
    From $378 per night (USD)

    VRBO

    Jasmine Place

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    WELCOME TO JASMINE PLACE! We are complying with the directives listed on the Monroe County website. Please be aware th ...

    From $378 per night (USD)

    VRBO

    Details
  • ORCHID ESCAPE~ Historic!
    From $500 per night (USD)

    VRBO

    "ORCHID ESCAPE"~ Historic!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...

    From $500 per night (USD)

    VRBO

    Details
  • It's A Salt Life After All
    From $83 per night (USD)

    VRBO

    It's A Salt Life After All

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...

    From $83 per night (USD)

    VRBO

    Details
  • Key West Sailing Adventure
    From $215 per night (USD)

    VRBO

    Key West Sailing Adventure

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Hurry book last minute summer vacation dates that just opened up now! This 37 foot boat is available Key West! This is ...

    From $215 per night (USD)

    VRBO

    Details
  • SEAPORT PANORAMA at Galleon Resort, Key West, FL (Beach-Pool-BBQ)
    Click For Pricing

    VRBO

    SEAPORT PANORAMA at Galleon Resort, Key West, FL (Beach-Pool-BBQ)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...

    Click For Pricing

    VRBO

    Details
  • Nassau Suite Key West
    From $168 per night (USD)

    VRBO

    Nassau Suite Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...

    From $168 per night (USD)

    VRBO

    Details
  • Sea Breeze Cottage
    From $100 per night (USD)

    VRBO

    Sea Breeze Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the beautiful Truman Annex. Get ready ...

    From $100 per night (USD)

    VRBO

    Details
  • Annie's Hideaway
    From $171 per night (USD)

    VRBO

    Annie's Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...

    From $171 per night (USD)

    VRBO

    Details
  • Pelican Landing Flamingo Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Flamingo Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Tranquility by the Beach C129
    From $240 per night (USD)

    VRBO

    Tranquility by the Beach C129

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...

    From $240 per night (USD)

    VRBO

    Details
  • Cigar Makers Tropical Cottage
    From $500 per night (USD)

    VRBO

    Cigar Makers Tropical Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Your tropical oasis in Historic Old Town Key West awaits for your monthly rental! 1890 Cigar Maker's Tropical Cottage re ...

    From $500 per night (USD)

    VRBO

    Details
  • THE QUARTERDECK ~ Vibrant!
    From $245 per night (USD)

    VRBO

    "THE QUARTERDECK" ~ Vibrant!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of ...

    From $245 per night (USD)

    VRBO

    Details
  • @@ Sunrise on the Atlantic @@
    From $335 per night (USD)

    VRBO

    @@ Sunrise on the Atlantic @@

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the ...

    From $335 per night (USD)

    VRBO

    Details
  • Hemingways Atlantic Retreat C339
    From $288 per night (USD)

    VRBO

    Hemingways Atlantic Retreat C339

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...

    From $288 per night (USD)

    VRBO

    Details
  • High Tide at Key West 1800 Atlantic Condos
    From $240 per night (USD)

    VRBO

    High Tide at Key West 1800 Atlantic Condos

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...

    From $240 per night (USD)

    VRBO

    Details
  • Luxury Island Gem A109
    From $125 per night (USD)

    VRBO

    Luxury Island Gem A109

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Garden View. 2 bedroom 2 full bathrooms, sleeps a max of 6. Luxurious tropical courtyard view two bedroom condo. This e ...

    From $125 per night (USD)

    VRBO

    Details
  • Puerta Coralina
    From $273 per night (USD)

    VRBO

    Puerta Coralina

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This precious ...

    From $273 per night (USD)

    VRBO

    Details
  • Old Town Charm Key West
    Click For Pricing

    VRBO

    Old Town Charm Key West

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...

    Click For Pricing

    VRBO

    Details
  • Beautiful Downtown Truman Annex Condo
    From $225 per night (USD)

    VRBO

    Beautiful Downtown Truman Annex Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...

    From $225 per night (USD)

    VRBO

    Details
  • Villa Fleur at Shipyard Condominiums
    From $79 per night (USD)

    VRBO

    Villa Fleur at Shipyard Condominiums

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...

    From $79 per night (USD)

    VRBO

    Details
  • IN GOOD SPIRITS ~ It's a Deal!
    From $193 per night (USD)

    VRBO

    "IN GOOD SPIRITS" ~ It's a Deal!

    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 $193 per night (USD)

    VRBO

    Details
  • Magic Ocean Penthouse
    From $274 per night (USD)

    VRBO

    Magic Ocean Penthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling wind ...

    From $274 per night (USD)

    VRBO

    Details
  • Blue Heron's Cove
    From $202 per night (USD)

    VRBO

    Blue Heron's Cove

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! BLUE HERON'S ...

    From $202 per night (USD)

    VRBO

    Details
  • Another Three Hour Tour
    From $207 per night (USD)

    VRBO

    Another Three Hour Tour

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $207 per night (USD)

    VRBO

    Details
  • Atlantic Docks Paradise C433
    From $134 per night (USD)

    VRBO

    Atlantic Docks Paradise C433

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths Elegant sophistication abound in this fabulous 2 bedroom 2 ...

    From $134 per night (USD)

    VRBO

    Details
  • Bayview Retreat
    From $599 per night (USD)

    VRBO

    Bayview Retreat

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...

    From $599 per night (USD)

    VRBO

    Details
  • Seventh Heaven
    From $496 per night (USD)

    VRBO

    Seventh Heaven

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! As if a vacat ...

    From $496 per night (USD)

    VRBO

    Details
  • THE SEASHELL ~ Spectacular!
    From $1195 per night (USD)

    VRBO

    "THE SEASHELL" ~ Spectacular!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $1195 per night (USD)

    VRBO

    Details
  • Bird of Paradise
    From $168 per night (USD)

    VRBO

    Bird of Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Like witnessi ...

    From $168 per night (USD)

    VRBO

    Details
  • A Key West Cottage
    From $517 per night (USD)

    VRBO

    A Key West Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is small ...

    From $517 per night (USD)

    VRBO

    Details
  • Shipyard 197
    From $214 per night (USD)

    VRBO

    Shipyard 197

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    7 night minimum rental. Paradise is definitely found in this Non-Smoking, first floor condo only two short blocks off of ...

    From $214 per night (USD)

    VRBO

    Details
  • STONE'S THROW ~ Delightful!
    From $89 per night (USD)

    VRBO

    "STONE'S THROW" ~ Delightful!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    CLOSE TO THE FUN.... This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer!  Liter ...

    From $89 per night (USD)

    VRBO

    Details
  • A Mangrove Snapper
    From $293 per night (USD)

    VRBO

    A Mangrove Snapper

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. ...

    From $293 per night (USD)

    VRBO

    Details
  • Driftwood Buoy
    From $414 per night (USD)

    VRBO

    Driftwood Buoy

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    A luxury, ocean front, 2 bedroom, (king in master, twins or twins as king in guest bedroom, queen sleeper in living room ...

    From $414 per night (USD)

    VRBO

    Details
  • Havana Daydream
    From $321 per night (USD)

    VRBO

    Havana Daydream

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...

    From $321 per night (USD)

    VRBO

    Details
  • Villa Vista
    From $50 per night (USD)

    VRBO

    Villa Vista

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...

    From $50 per night (USD)

    VRBO

    Details
  • ATLANTIC BREEZE ~ The Good Life!
    From $245 per night (USD)

    VRBO

    "ATLANTIC BREEZE" ~ The Good Life!

    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
  • The Plantation
    From $443 per night (USD)

    VRBO

    The Plantation

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    ‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...

    From $443 per night (USD)

    VRBO

    Details
  • Cool Breeze
    From $150 per night (USD)

    VRBO

    Cool Breeze

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...

    From $150 per night (USD)

    VRBO

    Details
  • A Bella Capri
    From $233 per night (USD)

    VRBO

    A Bella Capri

    Bedrooms:
    4.5
    Bathrooms:
    5
    Sleeps:
    10

    This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...

    From $233 per night (USD)

    VRBO

    Details
  • Tropical Breezes @ Truman Annex
    From $207 per night (USD)

    VRBO

    Tropical Breezes @ Truman Annex

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...

    From $207 per night (USD)

    VRBO

    Details
  • 42' Catamaran Lucy
    From $208 per night (USD)

    VRBO

    42' Catamaran "Lucy"

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    As you starting reading about my boat, I would like to tell you what we doing to protect traveling public from Covid-1 ...

    From $208 per night (USD)

    VRBO

    Details
  • Conch Retreat Condo
    From $100 per night (USD)

    VRBO

    Conch Retreat Condo

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of ...

    From $100 per night (USD)

    VRBO

    Details
  • Oyster's Pearl
    From $171 per night (USD)

    VRBO

    Oyster's Pearl

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...

    From $171 per night (USD)

    VRBO

    Details
  • Free Island Spirit  Escape A311
    From $125 per night (USD)

    VRBO

    Free Island Spirit Escape A311

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...

    From $125 per night (USD)

    VRBO

    Details
  • Elizabeth's Secret
    From $378 per night (USD)

    VRBO

    Elizabeth's Secret

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Elizabeth's Secret! NOW A 3 Bedroom home! A tranquil and secluded flourishing tropical oasis awaits you be ...

    From $378 per night (USD)

    VRBO

    Details
  • Pelican Landing Bonaire Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Bonaire Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Forever Young
    From $343 per night (USD)

    VRBO

    Forever Young

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    5

    This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...

    From $343 per night (USD)

    VRBO

    Details