Florida Keys Rentals
From $975 per night (USD)HomeAway
Key Largo 5/5, Pool, Jacuzzi, Outdoor Kitchen, Tiki Hut, 70 ft 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
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
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
From $221 per night (USD)VRBO
P68 - 371 8th St in Key Colony Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- 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
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
From $209 per night (USD)VRBO
Doctors Arm waterfront home. 75 feet of dock with plenty 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
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
From $154 per night (USD)VRBO
P10 - 111A Alynn in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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)VRBO
From $95 per night (USD)HomeAway
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)HomeAway
From $234 per night (USD)VRBO
P51 - 751 98th St in Marathon
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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
From $250 per night (USD)HomeAway
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)HomeAway
From $379 per night (USD)VRBO
P28 - 320 13th Street
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautifully remodeled, gourmet kitchen, granite counter tops throughout, new kitchen, all new appliances , new bathrooms ...
From $379 per night (USD)VRBO
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
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
From $345 per night (USD)HomeAway
"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)HomeAway
From $650 per night (USD)VRBO
"GARDEN HIDEAWAY"~ Beautiful lush landscaped oasis located in the Casa Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
PARADISE AWAITS... Newly renovation and furnished, charming home is located in one of the most desirable locations in Ke ...
From $650 per night (USD)VRBO
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
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
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. - D ...
From $200 per night (USD)HomeAway
From $221 per night (USD)VRBO
P78 - 497 Sombrero Beach Rd
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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
From $100 per night (USD)HomeAway
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)HomeAway
From $200 per night (USD)VRBO
Sunrise Retreat 3bed/2bath with private pool & dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Seven Night Minimum, NO EXCEPTIONS. Max Occupancy: 8 (NO MATTER THE AGE) This is a regulation set up by Key Colony Beac ...
From $200 per night (USD)VRBO
From $245 per night (USD)HomeAway
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)HomeAway
From $156 per night (USD)VRBO
P31 - 230 11th St, KCB
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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)VRBO
From $1295 per night (USD)HomeAway
"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)HomeAway
From $525 per night (USD)VRBO
"STARS" ~4 bedroom, 2 Bath Condo, Pool Heat, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $525 per night (USD)VRBO
From $300 per night (USD)HomeAway
Ocean Views in Paradise! 5308 Ocean Pointe Suites 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 bedroo ...
From $300 per night (USD)HomeAway
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
From $200 per night (USD)HomeAway
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)HomeAway
From $285 per night (USD)VRBO
P34 - 201 8th St, KCB
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Key Colony Beach, Florida One of Key Colony's finest: Exquisite and spacious 4 bedroom, 2 bathroom, private pool h ...
From $285 per night (USD)VRBO
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
From $321 per night (USD)VRBO
P74 - 23 Kyle Way in Marathon
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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)VRBO
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)HomeAway
From $550 per night (USD)VRBO
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 p ...
From $550 per night (USD)VRBO
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)HomeAway
From $500 per night (USD)VRBO
P12 - 1235 101St St Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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)VRBO
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)HomeAway
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
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)HomeAway
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)VRBO
From $209 per night (USD)HomeAway
Islamorada Home Plus Bunkhouse
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
New listing. Best location in the Florida Keys! Our home has 2 bedrooms with queen beds and pull out sofa in living room ...
From $209 per night (USD)HomeAway
From $150 per night (USD)VRBO
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)VRBO
From $159 per night (USD)HomeAway
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)HomeAway
From $150 per night (USD)VRBO
Pet Friendly/Fishing/Boating/Kayaking/Dining/Partial water views/Shopping/Bars
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
Book now don't wait. Dates are going fast. MM 90 This charming home is surrounded by mature trees making it very priv ...
From $150 per night (USD)VRBO
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)HomeAway
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)VRBO
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)HomeAway
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)VRBO
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
From $250 per night (USD)VRBO
"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)VRBO
From $249 per night (USD)HomeAway
Paradise In Key Largo: Recently Renovated Canal Front 3 Bedroom/3 Bath Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in a completely renovated canal front 3 bedroom/3 bath home with a new custom kitchen, bathrooms, cathedral ceiling ...
From $249 per night (USD)HomeAway
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
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
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
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
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
From $99 per night (USD)HomeAway
Beautiful & Tranquil Spacious Key Largo Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Very spacious double mobile home, built in 2014. Square footage of indoor living is 1500, 3 bedrooms, Master has a kin ...
From $99 per night (USD)HomeAway
From $300 per night (USD)VRBO
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)VRBO
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
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
From $200 per night (USD)HomeAway
Beautiful home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy all that Islamorada has to offer! Live the Keys life in this beautiful deep water canal front home. Lo ...
From $200 per night (USD)HomeAway
From $1195 per night (USD)VRBO
"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)VRBO
From $1455 per night (USD)HomeAway
"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)HomeAway
From $250 per night (USD)VRBO
"BELLA VITA" ~2/1.5 located in the Truman Annex with a community pool!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President`s Walk at Truman Annex. This well manicured commu ...
From $250 per night (USD)VRBO
From $125 per night (USD)HomeAway
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)HomeAway
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
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
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
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
From $200 per night (USD)VRBO
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)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
From $175 per night (USD)VRBO
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)VRBO
From $125 per night (USD)HomeAway
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)HomeAway
From $234 per night (USD)VRBO
Feb./March NOW OPEN Oceanfront Condo, Private Beach, Adult Community, Huge Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy Prestigious Castillo del Sol 2nd floor condo! Relax on one of the many lounge chairs on our private sandy beach or ...
From $234 per night (USD)VRBO
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
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
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)HomeAway
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)VRBO
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
From $207 per night (USD)VRBO
W13 - NEW HOME 794 26th Street
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Easy Access to Boot Key Harbor and Atlantic This perfectly situated rental is exactly what you've been searching f ...
From $207 per night (USD)VRBO
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
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
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
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
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
From $259 per night (USD)VRBO
Oceanside - Open Ocean Views - Modern Cottage With Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The recently renovated Oceanside House is located directly on the ocean with amazing morning sunrises over the ocean. T ...
From $259 per night (USD)VRBO
From $150 per night (USD)HomeAway
Your own Sunset from our own Private Balcony Directly over the Bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime co ...
From $150 per night (USD)HomeAway
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
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
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
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
From $141 per night (USD)VRBO
Key Colony Beach Condo 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
From $300 per night (USD)HomeAway
Clean Large 5BR Sleeps 12 Waterfront Home Ocean Side Deep Canal 68ft Dock Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to Marathon in this large 5 bedroom 3 bath waterfront home in the heart of Marathon Florida. This clean home is b ...
From $300 per night (USD)HomeAway
From $150 per night (USD)VRBO
IMMACULATE ONE BEDROOM CONDO WITH OCEAN VIEWS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come unwind at our newly renovated oceanfront condo in Islamorada. Enjoy breathtaking sunrises and sunsets, or scan the ...
From $150 per night (USD)VRBO
From $400 per night (USD)HomeAway
For the most discriminating traveler...525 Mariners Club Key Largo For the most discriminating traveler...525 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This sumptuous four bedroom oceanfront villa exudes luxury in every detail...the finest leather furnishings...custom woo ...
From $400 per night (USD)HomeAway
From $85 per night (USD)VRBO
Palm Island Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $125 per night (USD)HomeAway
Key Colony Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2/2 half duplex located on West Ocean Dr in Key Colony Beach. This unit has a king bed in the master and two twins in th ...
From $125 per night (USD)HomeAway
From $180 per night (USD)VRBO
Colony Poolside: A charming bungalow near the historic cemetery
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter th ...
From $180 per night (USD)VRBO
From $200 per night (USD)HomeAway
2 Bedroom 2.5 Bath Luxury Townhome in the Keys
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy memorable sunsets, magnificent bay / ocean views and revel in all the local charm and activities the Keys have to ...
From $200 per night (USD)HomeAway
From $175 per night (USD)VRBO
Villages at Hawks Cay Villa with Spa
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
In response to COVID-19, our villa will be disinfected and sanitized professionally prior to all check-ins. We offer ni ...
From $175 per night (USD)VRBO
From $749 per night (USD)HomeAway
~ CLOUD 9 ~ Perfect Home In Heart of Downtown KW w/ Heated Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
THE PROPERTY: The Absolute Best Luxury Private Vacation Rental Home by Duval Street In Old Town. Just a half block off ...
From $749 per night (USD)HomeAway