Florida Keys Rentals
From $317 per night (USD)VRBO
Blue Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $317 per night (USD)VRBO
From $326 per night (USD)Expedia
Green Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $326 per night (USD)Expedia
From $498 per night (USD)VRBO
SPECTACULAR Indigo Reef Waterfront Home #41 - Marathon, Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Indigo Reef #41 is the BEST KEPT SECRET in the Florida Keys!! This home is spectacular in every sense of the word and no ...
From $498 per night (USD)VRBO
From $452 per night (USD)Expedia
Angler's Retreat updated 3-bedroom, 2-bath home just minutes from Sombrero Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the Florida Keys in this beautifully updated 3-bedroom, 2-bath home just minutes from Sombrero Beach! The fully eq ...
From $452 per night (USD)Expedia
From $473 per night (USD)VRBO
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay with us at VENTURE OUT, a fantastic gated, activity filled community in Cudjoe Key, Fl- only 20 miles north of ...
From $473 per night (USD)VRBO
From $417 per night (USD)Expedia
Poolside King Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $417 per night (USD)Expedia
From $412 per night (USD)VRBO
Poolside Queen Room Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $412 per night (USD)VRBO
From $498 per night (USD)Expedia
One Bedroom Deck Villa Steps from Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $498 per night (USD)Expedia
From $607 per night (USD)VRBO
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $607 per night (USD)VRBO
From $4327 per night (USD)VRBO
Beautiful Florida Keys Oasis, private beach with magnificent sunsets
- Bedrooms:
- 11
- Bathrooms:
- 10
- Sleeps:
- 44
Nestled along the picturesque shores of Key Largo, Florida, Bahia Bay is a luxurious waterfront estate offering an unpar ...
From $4327 per night (USD)VRBO
From $181 per night (USD)VRBO
The Hideaway: Lose Yourself At This Recently Decorated Canal Front Home on Big Torch Key, Dockage!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $181 per night (USD)VRBO
From $548 per night (USD)Expedia
Sombrero Island Breeze 4BD Pool Paradise (M#9)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Indulge in five-star waterfront luxury at this stunning 4BR, 3BA retreat in one of the Keys' most unique island communit ...
From $548 per night (USD)Expedia
From $244 per night (USD)VRBO
Duval Street Suites on Duval Free Parking and heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duva ...
From $244 per night (USD)VRBO
From $296 per night (USD)Expedia
Duval Street Suites full kitchen, free parking, & heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic ...
From $296 per night (USD)Expedia
From $269 per night (USD)VRBO
Duval Street Suites full kitchen, free parking, heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Paradise Suite is a one bedroom (king bed) 1 bath suite with a murphy bed (queen) and kitchen. In historic Ol ...
From $269 per night (USD)VRBO
From $257 per night (USD)Expedia
Duval Street Suites full kitchen and pool view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and kitchen. Overlookin ...
From $257 per night (USD)Expedia
From $271 per night (USD)VRBO
Duval Street Suites with full kitchen heated pool, free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Mile Zero Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (king) and full kitchen. Overlooking ...
From $271 per night (USD)VRBO
From $1935 per night (USD)Expedia
6 BR 6 BA Duval Street Suites free parking & pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: This can accommodate 24 people, each apartment has 2 beds. You'll have privacy with six individual suites each ...
From $1935 per night (USD)Expedia
From $714 per night (USD)VRBO
P60 - 4 bedroom 4 bathroom home with pool and dockage. Amazing outside living space!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This fabulous 4 bedroom, 4.5 bathroom home was designed and built for comfort and style! Guests love the different theme ...
From $714 per night (USD)VRBO
From $1167 per night (USD)Expedia
Sombrero Beach house with private dock and pool
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 8
Casa MarBella @ Sombrero Beach offers plenty of indoor and outdoor space. Enjoy our beautiful pool with flowing waterfal ...
From $1167 per night (USD)Expedia
From $880 per night (USD)VRBO
ATLANTIS...Ocean Front Cottage Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need ...
From $880 per night (USD)VRBO
From $195 per night (USD)Expedia
MONTHLY Rental, JAN, FEB, MAR 2027 just opened, Old Town, pets ok
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Sea Monkey and The Mermaid! Our home is a duplex located in Old Town and full of Key West charm. Both unit ...
From $195 per night (USD)Expedia
From $552 per night (USD)VRBO
Sunset Villas: Bayfront Beach Compound<br>**28 Night Min**
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Sunset Villas is a boutique resort boasting 4 private villas on a Bayfront acre with one of the few swimmable sandy beac ...
From $552 per night (USD)VRBO
From $248 per night (USD)VRBO
Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Calusa resort is a gated community located in Key Largo. The resort rests on the peaceful edge of Buttonwood bay. Guests ...
From $248 per night (USD)VRBO
From $593 per night (USD)VRBO
Peaceful canal-front 3/3 Single-Family Home w/ Private Pool & Cabana Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Heron House, your private canal-front escape in the heart of Key Colony Beach. This ground-level, single ...
From $593 per night (USD)VRBO
From $204 per night (USD)Expedia
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 $204 per night (USD)Expedia
From $665 per night (USD)VRBO
Amazing Sunsets, Bay Breezes in the beautiful Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience ultimate relaxation at Anchors Aweigh, a modern 3-bedroom Key Largo home in the beautiful Florida Keys. Co ...
From $665 per night (USD)VRBO
From $610 per night (USD)Expedia
115 Mariners Club Spacious Villa with Resort Pools
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
As you enter this marina-front villa in Key Largo, the coastal view captivates you, showcasing the private yacht harbor ...
From $610 per night (USD)Expedia
From $490 per night (USD)VRBO
Poolside Suite - Pool & Close to Duval Street
- 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 hea ...
From $490 per night (USD)VRBO
From $354 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 $354 per night (USD)Expedia
From $209 per night (USD)VRBO
Away From It All @ The 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 $209 per night (USD)VRBO
From $555 per night (USD)Expedia
Coral Lagoon #13: Heated Pool, Views, easy Gulf & Atlantic Access via Vaca Cut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coral Lagoon #13: Pool, Water Views, Located just off Vaca Cut with easy Gulf & Atlantic Access. ** CHECK OUT OUR REVIE ...
From $555 per night (USD)Expedia
From $596 per night (USD)VRBO
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 $596 per night (USD)VRBO
From $375 per night (USD)Expedia
*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 $375 per night (USD)Expedia
From $440 per night (USD)VRBO
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 $440 per night (USD)VRBO
From $451 per night (USD)Expedia
Lagoon View Retreat • 2 Kings• Pickleball• Marina
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
TAKE A VIRTUAL TOUR OF THE ENTIRE UNIT BEFORE BOOKING http:www.youtube.com/@Keylargotravels This property is managed b ...
From $451 per night (USD)Expedia
From $717 per night (USD)VRBO
P18 - Spectacular 4 bedroom home with dockage and oversized private pool in Key Colony!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Boat Drinks Bungalow This lovely 4 bedroom, 4 bath home is located in the highly desirable area of Key Colony Beach. ...
From $717 per night (USD)VRBO
From $1636 per night (USD)Expedia
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Seaside Place welcomes guests from all states and follows all cleanliness and safety guidelines. Your safety and comfor ...
From $1636 per night (USD)Expedia
From $157 per night (USD)VRBO
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 $157 per night (USD)VRBO
From $337 per night (USD)Expedia
Vibrant Family Condo with Pool & Ocean Panorama U3
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy vibrant living at our 2-bedroom Colourful Keys Condo, where fun meets relaxation. Boasting pool and ocea ...
From $337 per night (USD)Expedia
From $633 per night (USD)VRBO
P82 - Sombrero Beach - 4 bedroom pool home with dock and private ramp.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sombrero Beach Sea-clusion awaits our guests! Get ready to create great vacation memories! This spacious 4-bedroom, 3 a ...
From $633 per night (USD)VRBO
From $859 per night (USD)Expedia
3bed vacation ocean side townhome 2pools,marina,lagoon,golf cart,bikes,kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Family and Friends vacation in mind - beautiful Key Largo townhouse with 2 separate living rooms which that offers a un ...
From $859 per night (USD)Expedia
From $940 per night (USD)VRBO
**THE ZESTY LIME @ OLD TOWN** Restored Home + Last Key White Glove Service...
- Bedrooms:
- 3
- 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 $940 per night (USD)VRBO
From $370 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 $370 per night (USD)Expedia
From $282 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
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $282 per night (USD)VRBO
From $486 per night (USD)Expedia
Reel Paradise I - 2bed/2bath half duplex with private pool & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Reel Paradise 1, a charming 2-bedroom, 2-bath half duplex designed for the perfect Florida Keys getaway. This ...
From $486 per night (USD)Expedia
From $853 per night (USD)VRBO
P87 - Modern 4 bedroom, 4 bath home on open water in Sombrero Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning views with premier Sombrero Beach location sets this home apart from all others! This ocean front home is spect ...
From $853 per night (USD)VRBO
From $1398 per night (USD)Expedia
Elev • 5BR/8BA • Game Room • 75’ Deep Canal Dock • Ice Maker • Kayaks • Bikes
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your private Mediterranean-style paradise in Key Colony Beach, proudly known as the Gem of the Keys. This lux ...
From $1398 per night (USD)Expedia
From $413 per night (USD)VRBO
Waterfront Community in Key Largo, Florida - Moon Bay Condo A210 Sunsets
- Bedrooms:
- 1
- 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 $413 per night (USD)VRBO
From $256 per night (USD)Expedia
Duval Street Suites full kitchen Old Town with heated 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 ...
From $256 per night (USD)Expedia
From $628 per night (USD)VRBO
Oceanside Kawama Villa R5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Come experience ultimate relaxation and comfort in this stunning three-story vacation home. On the first floor, you will ...
From $628 per night (USD)VRBO
From $2112 per night (USD)Expedia
Thompson Island - Private Island Estate in Key West
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 20
Thompson Island is the only private island in Key West with direct bridge access. Guests drive across a private bridge, ...
From $2112 per night (USD)Expedia
From $237 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Keys Life Cottage! Experience the laid-back charm of Islamorada at Keys Life Cottage, a beautifully coastal- ...
From $237 per night (USD)VRBO
From $492 per night (USD)Expedia
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront Oasis in Key West – Steps from Smathers Beach Escape to paradise in this spacious 2-bedroom, 2-bath condo wi ...
From $492 per night (USD)Expedia
From $405 per night (USD)VRBO
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Caribbean Conch – Your Island Retreat Awaits Escape to the serene beauty of Caribbean Conch, a spacious and ...
From $405 per night (USD)VRBO
From $596 per night (USD)Expedia
Key Largo Ocean Shore Villa 3 with pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This centrally located boater`s paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $596 per night (USD)Expedia
From $324 per night (USD)VRBO
P11 - Charming 2 bedroom 2 bath duplex with private pool and dock - Completely updated.
- 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 $324 per night (USD)VRBO
From $900 per night (USD)Expedia
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Best vacation rental to explore the Florida keys. Marina Villa 210 (3b/3b) with Marina and ocean views. Escape to pa ...
From $900 per night (USD)Expedia
From $1125 per night (USD)VRBO
Waterfront, 100ft Dock, Kayaks, Bikes, Pool, Hot Tub, Basketball & Pickleball
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
WELCOME TO COCO PLUM ON THE BAY - MARATHON, FLORIDA KEYS Welcome to Coco Plum on the Bay, your private waterfront retre ...
From $1125 per night (USD)VRBO
From $385 per night (USD)Expedia
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 $385 per night (USD)Expedia
From $395 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 2
- 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 $395 per night (USD)VRBO
From $1007 per night (USD)Expedia
W09 - New Luxury Property! Breathtaking Canal Front Pool Home - Sleeps 14
- Bedrooms:
- 6
- 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 $1007 per night (USD)Expedia
From $459 per night (USD)VRBO
**TIDEWATER VIEWS** Cottage + Boat Slip + Pool + Last Key White Glove Service...
- 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 $459 per night (USD)VRBO
From $783 per night (USD)Expedia
Beautiful 4 Bedroom, 3 Bath, Spacious Pool/SPA Home with 200' wide Canal.
- Bedrooms:
- 3
- 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 $783 per night (USD)Expedia
From $438 per night (USD)VRBO
Little Island Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Paradise in Key Colony Beach, Florida Keys Dreaming of a relaxing getaway in the beautiful Florida Keys? Welc ...
From $438 per night (USD)VRBO
From $384 per night (USD)Expedia
B105 Moon Bay - 3 bedroom townhouse includes studio apartment and boat dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor, and a studio apartment on the ground floor with ...
From $384 per night (USD)Expedia
From $575 per night (USD)VRBO
Great Location , Great Vibes, Great Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon an ...
From $575 per night (USD)VRBO
From $379 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 $379 per night (USD)Expedia
From $499 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 $499 per night (USD)VRBO
From $542 per night (USD)Expedia
Key Largo Ocean Shore Villa 1 with pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in the heart of the Florida Keys, this one-of-a-kind vacation rental offers the perfect combination of luxury an ...
From $542 per night (USD)Expedia
From $382 per night (USD)VRBO
Resort Condo with Marina Views, Pool, Tiki, Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, is the perfect getaway, accommodating up to 4 ...
From $382 per night (USD)VRBO
From $395 per night (USD)Expedia
**DANCE OF THE BUTTERFLIES** New Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For a month i ...
From $395 per night (USD)Expedia
From $502 per night (USD)VRBO
207 Mariners Club - Well appointed 3 bedroom, 3 Bath Townhome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly located along the picture-perfect marina front overlooking the beautifully landscaped gardens of Mariners Club ...
From $502 per night (USD)VRBO
From $670 per night (USD)Expedia
611 Mariners Club - 4 bedroom townhome, spacious luxury for friends and family
- 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 $670 per night (USD)Expedia
From $892 per night (USD)VRBO
**THE TOASTED COCONUT @ OLD TOWN** Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $892 per night (USD)VRBO
From $344 per night (USD)Expedia
P63 - Beautiful, waterfront duplex, walking distance to The Cabana Club!
- 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 $344 per night (USD)Expedia
From $566 per night (USD)VRBO
M12 - Beautiful house in Key Colony offering 4 bedrooms, pool and dockage!
- 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 $566 per night (USD)VRBO
From $297 per night (USD)Expedia
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 $297 per night (USD)Expedia
From $265 per night (USD)VRBO
M123 - Cabana Beach Duplex! Premier location across the street from Cabana Beach Club!
- 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 $265 per night (USD)VRBO
From $270 per night (USD)Expedia
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 $270 per night (USD)Expedia
From $263 per night (USD)VRBO
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 $263 per night (USD)VRBO
From $545 per night (USD)Expedia
Key Lime Villa #42 Indigo Reef | Boat Slip + Sunset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom features its own televisi ...
From $545 per night (USD)Expedia
From $409 per night (USD)VRBO
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This Private Canal front Pool/TIKI home with Dock, sits in Port Pine Heights BIG PINE KEY FL. See key deer every day wa ...
From $409 per night (USD)VRBO
From $440 per night (USD)Expedia
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Sea Biscuit houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $440 per night (USD)Expedia
From $203 per night (USD)VRBO
2 Bdrm Ocean Breezes Tropical Island Key West Sunrises Resort amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Elegant Ocean-View Condo at 1800 Atlantic – Fully Renovated 2BR/2BA Experience refined coastal living in this beautiful ...
From $203 per night (USD)VRBO
From $172 per night (USD)Expedia
Florida Escape 2 bdrm monthly spacious resort amenities Key West Mid Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our piece of paradise in Key West! Our beautifully maintained, fully tiled 2-bedroom condo is your perfect ho ...
From $172 per night (USD)Expedia
From $859 per night (USD)VRBO
409 Mariners Club - 3 bedroom townhome with breathtaking ocean views
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Instantly feel the warmth of the island spirit as you enter this recently renovated and refreshed 3-bedroom, 4-bath, tri ...
From $859 per night (USD)VRBO
From $236 per night (USD)Expedia
Condo in the Keys, Peaceful ocean view retreat!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
<p>Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Ke ...
From $236 per night (USD)Expedia
From $1453 per night (USD)VRBO
Contra House - Private Pool & Steps to Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home ...
From $1453 per night (USD)VRBO
From $567 per night (USD)Expedia
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming Historic Bungalow with Private Pool & Detached Cottage – Steps from Duval Street! Experience the best of Key W ...
From $567 per night (USD)Expedia
From $442 per night (USD)VRBO
Fishermen's Paradise- Private Pool, Hot Tub, Quick Access To Ocean, 60 ft Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
NO PETS. NO SMOKING NO EXCEPTIONS... This is a pet free and smoke free property. If you show up with a pet you will no ...
From $442 per night (USD)VRBO
From $419 per night (USD)Expedia
Modern Nautical Townhome on Moonbay Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to a piece of paradise! This is a beautiful two-story townhouse that has been newly furnished. Upstairs you will ...
From $419 per night (USD)Expedia
From $512 per night (USD)VRBO
🌸Home(#3) BIKINI👙 BOTTOM (Partial View Property-approximately 200 ft from private beach entrance🌸
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
🌸Home(#3) BIKINI👙 BOTTOM (Partial View Property-approximately 200 ft from private beach entrance 👙Totally Private😉- ...
From $512 per night (USD)VRBO
From $359 per night (USD)Expedia
Paradise Found – Oceanfront Condo w/ Pool Views & Private Beach in Key Colony!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Competently remodeled from quartz countertops in kitchen and both full bathrooms. New doors throughout the unit with up ...
From $359 per night (USD)Expedia
From $471 per night (USD)VRBO
Summer Vacation at Gulf side Gem! 45 ft. Dock, pool , hot tub and more
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape Winter and experience Warm Florida Key Weather and Calm Water for Fishing! Great Getaway for couples and a group ...
From $471 per night (USD)VRBO
From $496 per night (USD)Expedia
DUPLEX IN DUCK KEY, 2 Bedroom /2 Bath w/40' Dock, Trailer Storage Incl.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $496 per night (USD)Expedia
From $835 per night (USD)VRBO
Waterfront Luxury Villa (62) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This renovated and spacious 3BD, 3.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom includes it ...
From $835 per night (USD)VRBO
From $1073 per night (USD)Expedia
Beautiful Ocean Front View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunni ...
From $1073 per night (USD)Expedia
From $396 per night (USD)VRBO
Ocean view condo with balcony/marina view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in ...
From $396 per night (USD)VRBO
From $962 per night (USD)Expedia
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $962 per night (USD)Expedia