Florida Keys Rentals
- From $144 per night (USD)
VRBO
Key Largo, Calusa, 2 bedroom 1.5 bath with screened in patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Calusa resort is a gated community located in Key Largo. Community rests on Buttonwood bay. Guests are sure to enjoy a m ...
From $144 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Quiet canal-front 3\/3 Single-Family with Private Pool & Cabana Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron House. Enjoy and relax in our ground-level 3 bedroom / 3 bathroom private, single-family home whi ...
From $415 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Easy Ocean Access House 30' Dock & Pool at Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our Beach House in the prestigious Key Colony Beach. 30 FT dock house in a 90 FT canal with easy access to th ...
From $303 per night (USD)VRBO
- From $476 per night (USD)
Expedia
Amazing Views in Florida Keys Bayside BAY BREEZES, SUNSETS, SAILBOATS n SEAGULLS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make memories that last a lifetime at Anchors Aweigh - experience Bay Breezes, Sunsets, Sailboats n Seagulls with this p ...
From $476 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Tropical oasis near all the action with central AC & balcony
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Villa #7103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $251 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Inspired by home...115 Mariners Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Key Largo’s coastal setting beckons from inside your marina-front villa as you enter through the front door with a spect ...
From $450 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Poolside Suite by Brightwild | Pvt Pool & Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Poolside Suite is the PERFECT vacation home for family and friends looking for a fun-filled getaway in the hear ...
From $328 per night (USD)VRBO
- From $309 per night (USD)
Expedia
Cozy Home!!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated half duplex on a quiet street in Marathon. Conveniently located in the heart of Marathon, on a canal jus ...
From $309 per night (USD)Expedia
- From $150 per night (USD)
VRBO
PARADISE FOUND - ISLAMORADA FLORIDA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
BEAUTIFUL THREE BEDROOM, 2 FULL SIZE BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VI ...
From $150 per night (USD)VRBO
- From $307 per night (USD)
Expedia
AWAY FROM IT ALL at The Truman Annex in Key West
- 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 $307 per night (USD)Expedia
- From $473 per night (USD)
VRBO
Keys Vacation Price Drop! Book Now! New lower rates for Sep 5 - Nov 4, 2023
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
** CHECK OUT OUR REVIEWS!..... Come see why The BeachComer is truly "Paradise" in the Keys! ** Thank you for your inter ...
From $473 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Galleon Resort beach hotel luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $395 per night (USD)Expedia
- From $290 per night (USD)
VRBO
*New Modern* 3br\/2ba Duplex\/37' Dock\/Cabana\/Kayaks\/Bikes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly situated in KCB w/ 37.5 feet of dockage on a wide and pristine canal that leads easy access to both the Ocean ...
From $290 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $315 per night (USD)Expedia
- From $415 per night (USD)
VRBO
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $415 per night (USD)VRBO
- From $444 per night (USD)
Expedia
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please check out our other properties in Kawama by entering the following property numbers in the section "where do you ...
From $444 per night (USD)Expedia
- From $982 per night (USD)
VRBO
P18 - 261 12th St in Key Colony Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely 4 bedroom, 4 bath home is located in the highly desirable area of Key Colony Beach. *Please be ...
From $982 per night (USD)VRBO
- From $1491 per night (USD)
Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1491 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Gorgeous 3\/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Townhome with all extras. Keys style with beautiful furnishings, newly remodeled with three bedrooms plus oversized lof ...
From $300 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Enjoy this relaxing beachy house on a canal flowing into sexton cove bay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy this cozy home with a beautiful water front terrace. Conveniently located close to grocery stores, great restaura ...
From $175 per night (USD)Expedia
- Click For Pricing
VRBO
Vibrant Family Condo \/ Pool & Ocean Panorama
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy vibrant living at our 2-bedroom Colourful Keys Condo, where fun meets relaxation. Boasting pool and ocean views, t ...
Click For PricingVRBO
- From $564 per night (USD)
Expedia
P82 - Sombrero Beach - 4 bedroom pool home with dock and private ramp.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4- ...
From $564 per night (USD)Expedia
- From $554 per night (USD)
VRBO
3bed 3bth 3story ocean side townhome 2pools,marina,lagoon,golf cart,BBQ MM100
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Brand new appliances,floors, decor and more.. This upgraded Key Largo townhouse has 2 living rooms. This offers a uniqu ...
From $554 per night (USD)VRBO
- From $799 per night (USD)
Expedia
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is k ...
From $799 per night (USD)Expedia
- From $287 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ a patio 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 $287 per night (USD)VRBO
- From $392 per night (USD)
Expedia
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $392 per night (USD)Expedia
- From $209 per night (USD)
VRBO
Pool View & Pvt Balcony | Samana Cay Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $209 per night (USD)VRBO
- From $213 per night (USD)
Expedia
The Grand Turk by Brightwild | Sunset View & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the fun-filled Sunrise Suites complex located on the quiet side of Key West. - Just 1 mile from th ...
From $213 per night (USD)Expedia
- From $285 per night (USD)
VRBO
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Salty Sailfish, a magnificent canal-front home nestled on Cudjoe Key. With updated furnishings and a comm ...
From $285 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Paradise in Key Colony with Cabana Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This is a fisherman's dream rental. 3/2 half duplex in Key Colony Beach. By water 5 min. to the Atlantic and 15 min. to ...
From $298 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Reel Paradise I 2bed\/2bath updated half duplex with brand new private pool, deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This two bedroom two bath half duplex is recently remodeled and updated with brand new everything! The kitchen & living ...
From $320 per night (USD)VRBO
- From $667 per night (USD)
Expedia
P87 - New Construction house. 4 bedrooms, open water view - Sombrero Beach home!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning views with premier Sombrero Beach location set this home apart from all others. This ocean front home is specta ...
From $667 per night (USD)Expedia
- From $115 per night (USD)
VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $115 per night (USD)VRBO
- From $1237 per night (USD)
Expedia
Costamar 5 bed 7 bath pool boat dock bikes
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Brand new! Mediterranean Style Residential Home - 5 bedrooms, 5 full bathrooms, 2 half bathroom, pool/spa boat dock, o ...
From $1237 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Moon Bay, a piece of paradise! It is located on Blackwater Sound in Key Largo, Florida. Unit A210 is an end ...
From $375 per night (USD)VRBO
- Click For Pricing
Expedia
Key Largo Beautiful House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream vacation in a gorgeous 3 bedroom, 2 bathroom house, with bay views on one side and a canal view on ...
Click For PricingExpedia
- From $257 per night (USD)
VRBO
Duval Street Suite full kitchen Old Town with pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key Lime Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and full kitchen complete w ...
From $257 per night (USD)VRBO
- From $528 per night (USD)
Expedia
GREAT LOCATION! VILLA R5,MARINA, BEACH, LAGOON, 2POOLS,TENNIS,KAYAKS&BIKES
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
IF YOUR DATES ARE NOT AVAILABLE, PLEASE SEE OUR OTHER PROPERTIES AND REVIEWS in Kawama by entering the following propert ...
From $528 per night (USD)Expedia
- From $1699 per night (USD)
VRBO
BEAUTIFUL SANTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 20
A Castle on an Island On A Privately Owned Key West Island Private Bridge for Cars and Trucks connected to Key West Fr ...
From $1699 per night (USD)VRBO
- From $204 per night (USD)
Expedia
Oceanfront escape with pool, hot tub, marina, & central AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Aqua Vista: Ocean Pointe #3307 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $204 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Relax in Paradise! Enjoy a tropical lifestyle.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Impeccable 42' Luxury RV: One bedroom, loft with 3 beds,1 Bath stylish kitchen and living areas. Welcoming and spacious ...
From $199 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Historic Caroline Street Condo!1 Bedroom 2 Bath, Pool, Amazing Old Town Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history ...
From $275 per night (USD)Expedia
- Click For Pricing
Expedia
Sunrise Retreat 3bed\/2bath | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the Keys in style and comfort! This luxurious 3 bedroom 2 bath canal front home is located in prestigious and fam ...
Click For PricingExpedia
- From $782 per night (USD)
Expedia
Luxurious waterfront home with panoramic views, pool, spa, & dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Plein Air Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $782 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the "Keys Life Cottage!" This beautifully updated and spacious two bedroom, one bath home is tucked away on ...
From $140 per night (USD)VRBO
- From $322 per night (USD)
Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- 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 $322 per night (USD)Expedia
- From $423 per night (USD)
VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Caribbean Conch is a fantastic rental with a great location close to the pool. This unit features an extra large floor p ...
From $423 per night (USD)VRBO
- From $693 per night (USD)
Expedia
BEST LOCATION! VILLA 3, BOAT SLIP, POOL, KAYAKS, BIKES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
THIS PROPERTY HAS THE REQUIRED PERMITS PER MONROE COUNTY FOR VACATION RENTALS LOW FEES! NO HIDDEN FEES OR EXTRA CHARGES ...
From $693 per night (USD)Expedia
- Click For Pricing
VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For PricingVRBO
- From $213 per night (USD)
Expedia
The Trinidad by Brightwild | Pool View & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $213 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Coral Club Condo - Your Slice of Paradise in the Sombrero Beach Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Club Condo is your tropical haven in the serene Sombrero Beach Neighborhood, just a brief 10-minute walk from the ...
From $179 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Casa de Coco - Beautiful Ground Level Ocean Front Home.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This rental encompasses the ground-level 2-bedroom section of the residence, ensuring your exclusive occupancy of the pr ...
From $450 per night (USD)Expedia
- From $264 per night (USD)
VRBO
P11 - Charming 2 bedroom 2 bath duplex with private pool and dock -...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely 2 bedroom, 2 bath home is located on the gulfside with immediate Gulf water access and near the Vaca Cut for ...
From $264 per night (USD)VRBO
- From $567 per night (USD)
Expedia
Irresistible Ocean View! 335 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Infinite horizons...from this third floor, luxury, three-bedroom, two and one-half bath villa! A peaceful, relaxing get ...
From $567 per night (USD)Expedia
- From $673 per night (USD)
VRBO
Beautiful Marina Villa in Mariner's Club. Best New Listing November 2021.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 3 bathroom Luxurious Villa remodeled in 2021 in the exclusive Mariner's Club of Key Largo, Florida. This prop ...
From $673 per night (USD)VRBO
- From $900 per night (USD)
Expedia
Waterfront, 100ft Boat Dock, Kayaks, Paddle boards, Bikes, Private Pool, Sunsets
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Coco Plum on the Bay, your private waterfront single family home in Marathon, FL. You will enjoy a spacious ...
From $900 per night (USD)Expedia
- From $250 per night (USD)
VRBO
RV Camper in the heart of Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A beautiful RV camper right in the middle of paradise. A beautiful ambiance with such friendly neighbors. You wake up an ...
From $250 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $270 per night (USD)Expedia
- From $836 per night (USD)
VRBO
W09 - New Luxury Property! Breathtaking Canal Front Pool Home - Sleeps 14
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to paradise! Escape to this luxurious 6 bedroom/6.5 bathroom home designed for VIP guests. Each bedroom i ...
From $836 per night (USD)VRBO
- From $187 per night (USD)
Expedia
Charming dog-friendly home surrounded by palm trees Close to attractions
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Barefoot Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $187 per night (USD)Expedia
- From $305 per night (USD)
VRBO
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $305 per night (USD)VRBO
- From $231 per night (USD)
Expedia
Tropical Getaway in Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bedr ...
From $231 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Beautiful 4 Bedroom, 3 Bath, Spacious Pool\/SPA Home with 200' wide Canal.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Casa del Cielo. Enjoy breathtaking views of the Gulf and Ocean from this beautiful canal front home. Bring y ...
From $600 per night (USD)VRBO
- From $248 per night (USD)
Expedia
Airy, dog-friendly condo with pool, AC, high-speed WiFi, balcony, & hot tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Butterfly Nest 107 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $248 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Little Island Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have you been dreaming of a get away in the Florida Keys in Key Colony Beach. A little piece of heaven with a brand ne ...
From $304 per night (USD)VRBO
- From $293 per night (USD)
Expedia
Unique design! 3-bedroom townhouse includes studio apartment and boat dockage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
7-night minimum stay requirement. Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor and a stu ...
From $293 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Great Location , Great Vibes
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Quiet, secluded Keys house ideal for larger groups of friends and family's. Equal distance to Marathon and Key West. ...
From $400 per night (USD)VRBO
- From $434 per night (USD)
Expedia
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $434 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $304 per night (USD)VRBO
- From $393 per night (USD)
Expedia
BEST LOCATION! VILLA 1, BOAT SLIP, POOL, KAYAKS, BIKES, DIRECT OCEAN ACCESS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
THIS PROPERTY HAS THE REQUIRED PERMITS FROM MONROE COUNTY FOR VACATION RENTALS. LOW FEES! NO HIDDEN FEES OR EXTRA CHAR ...
From $393 per night (USD)Expedia
- From $308 per night (USD)
VRBO
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a TROPICAL ISLAND villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 2 villas ...
From $308 per night (USD)VRBO
- From $474 per night (USD)
Expedia
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $474 per night (USD)Expedia
- From $263 per night (USD)
VRBO
Marina, Resort Pool, Tiki Bar & Restaurant, Pickleball, Beach, Waterfront & more
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE DAPPER DOLPIN updated coastal themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete ...
From $263 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Efficient Oceanfront Condo W\/ Boat Dock, Private Balcony, & Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
98th Street Retreat Side B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $175 per night (USD)Expedia
- From $286 per night (USD)
VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a month i ...
From $286 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Marina front townhouse with garage! 207 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly located along the picture perfect marina front overlooking the beautifully landscaped gardens of Mariners Club ...
From $475 per night (USD)Expedia
- From $627 per night (USD)
VRBO
4 bed 4 bath - Sleeps 10! 611 Mariners Club Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This luxury Key Largo vacation townhome rental (Unit 611) is a 4 bedroom/4 bath unit. Ideal accommodations for the Flori ...
From $627 per night (USD)VRBO
- From $809 per night (USD)
Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $809 per night (USD)Expedia
- From $339 per night (USD)
VRBO
P63 - Beautiful, waterfront Key Colony Duplex. Short walk to the Cabana Beach...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $339 per night (USD)VRBO
- From $549 per night (USD)
Expedia
M12 - Beautiful new construction house offering 4 bedrooms, pool and on the...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 3 bathroom home in the heart of the Florida Keys is located in the very desirable Key Colony Beach and w ...
From $549 per night (USD)Expedia
- From $281 per night (USD)
VRBO
M18 - Spacious 3 bedroom, 2 bath Gulf side condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious 3 bedroom, 2 bathroom, second floor condo, with split floor plan. Large screened wrap around porc ...
From $281 per night (USD)VRBO
- From $217 per night (USD)
Expedia
M123 - Cabana Beach Duplex! Premier location across the street from Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This comfy, cozy 2 bedroom, 2 bathroom duplex is ideally located in the heart of the Keys in Key Colony Beach. ...
From $217 per night (USD)Expedia
- From $523 per night (USD)
VRBO
Luxury and Lovely Water Front House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of M ...
From $523 per night (USD)VRBO
- From $224 per night (USD)
Expedia
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $224 per night (USD)Expedia
- Click For Pricing
VRBO
Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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- Click For Pricing
Expedia
Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
Click For PricingExpedia
- Click For Pricing
VRBO
Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
Click For PricingVRBO
- Click For Pricing
Expedia
Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
Click For PricingExpedia
- Click For Pricing
VRBO
Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large living room with water view and deck. Deck off Master Bedroom overlooking the Adams cut waterway and pool. Relax ...
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- Click For Pricing
Expedia
Water front property with bar, tennis, market place, and restaurants close by.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Comfortable home with 2 bedrooms and a bath on both upper level and lower level. Great for fishing and kayaking, has a d ...
Click For PricingExpedia
- From $280 per night (USD)
VRBO
Ocean Pointes Finest Master Suite W\/ Endless Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Beautifully designed 1 bedroom 2 bath corner suite in Ocean Pointe Suites; a private gated community nestled on the Atla ...
From $280 per night (USD)VRBO
- From $238 per night (USD)
Expedia
The Barbados by Brightwild | Balcony & Pool View!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $238 per night (USD)Expedia
- From $159 per night (USD)
VRBO
Immaculate oceanfront townhouse with ocean view & private beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Duck Key Retreat Villa #5105 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $159 per night (USD)VRBO
- From $286 per night (USD)
Expedia
Dog-Friendly, Waterfront Duplex with Dock, WiFi, and Private Washer\/Dryer!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Teal Macaw Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $286 per night (USD)Expedia
- From $165 per night (USD)
VRBO
**FAIRWAY TO HEAVEN @ THE GOLF CLUB** Lavish Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ‘There’s a fe ...
From $165 per night (USD)VRBO
- Click For Pricing
Expedia
Modern Key Largo Waterfront Bayside Home - Dock your boat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WWW.MEETMEINKEYLARGO.COM Impeccable Waterfront Home in Key Largo on the bayside. This beautiful stilted home is new co ...
Click For PricingExpedia
- From $392 per night (USD)
VRBO
Atocha Cottage by Brightwild | Amazing Find!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport district of ...
From $392 per night (USD)VRBO
- Click For Pricing
Expedia
Affordable, Adorable home waiting for you in Cudjoe Key
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelv ...
Click For PricingExpedia
- From $346 per night (USD)
VRBO
Waterfront luxury Villa (42) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $346 per night (USD)VRBO
- From $413 per night (USD)
Expedia
The most set up home in BPK TIKI HUT ,POOL ,GRILL ,CANAL FRONT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Enjoy having ONLY1 neighbors directly next to you on top of being Just 6 houses from the open water. This Beautiful ful ...
From $413 per night (USD)Expedia