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Vacation rental houses in Key West

Vacation rental houses in Key West

Book beachfront vacation rental houses, houseboats, and more on Airbnb

Top-rated houses in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Big Blu - 5 bedroom, 4 bath in old town
SUPERHOST
Entire house · 12 guests · 5 beds · 4 baths

Big Blu - 5 bedroom, 4 bath in old townNEW ON THE RENTAL MARKET Big Blu is a recently renovated five bedroom, four bathroom traditional shotgun house with a twist! In addition to the three bedrooms in the main house, Big Blu has two master suites that have both common and private entrances. The main living area is a large and spacious space with a vaulted, post and beam ceiling that opens onto the backyard with a large heated pool with jacuzzi jets! Play bocce on the back lawn or sip Gin and Tonics while lounging poolside.

Old Town - Room Opens to Private Pool and Garden
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Old Town - Room Opens to Private Pool and GardenLocated in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Bring Your Boat! 2 BR/2BA Waterfront Paradise!
SUPERHOST
Entire house · 4 guests · 2 beds · 2 baths

Bring Your Boat! 2 BR/2BA Waterfront Paradise!Bring your boat and enjoy the ideal Florida Keys waterfront location! SLACK TIDE is located on Cudjoe Key, on the Atlantic side of the Overseas Highway at mile marker 23. Situated on a 60 ft wide, deep water canal with direct access to the Atlantic Ocean, it's easy to relax and enjoy the incredible open water views and 35 ft of dock space for your boat. We encourage you to use the 2 kayaks and 1 paddle board we keep onsite to explore the gorgeous Florida Keys waters right outside the back door.

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Apartments
  • Unique stays

Popular house amenities in Key West

  • Pool
  • Air conditioning
  • Kitchen
  • Wifi
  • Pets allowed

Apartments in Key West

1 bedroom Cottage
SUPERHOSTEntire apartment
1 bedroom Cottage
Price:R3,546 ZAR / night
Duval Street Duplex w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Duplex w/ Balcony and Parking
Price:R4,488 ZAR / night
Key West Suites Hotel #205
SUPERHOSTEntire apartment
Key West Suites Hotel #205
Price:R3,091 ZAR / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Price:R3,844 ZAR / night
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
Price:R2,957 ZAR / night
Key West - Sunrise ❀ The Green House
SUPERHOSTEntire apartment
Key West - Sunrise ❀ The Green House
Price:R2,619 ZAR / night
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
Price:R2,980 ZAR / night
Duval Balcony Spanky's Retreat
SUPERHOSTEntire apartment
Duval Balcony Spanky's Retreat
Price:R2,443 ZAR / night
Key West - Sunset ❀ The Green House
SUPERHOSTEntire apartment
Key West - Sunset ❀ The Green House
Price:R2,802 ZAR / night
Historic Caroline St. Apartment 1
Entire apartment
Historic Caroline St. Apartment 1
Price:R2,543 ZAR / night
Duval Street Apartment w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Apartment w/ Balcony and Parking
Price:R3,309 ZAR / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
Price:R5,732 ZAR / night

Pet-friendly houses

Big Bertha
Entire house
Big Bertha
Price:R3,502 ZAR / night
Pet Friendly Monthly Key West Rental
Entire house
Pet Friendly Monthly Key West Rental
Price:R5,330 ZAR / night
**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Entire house
**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Price:R4,172 ZAR / night
Clean and Bright Key West Inspired Home
SUPERHOSTEntire house
Clean and Bright Key West Inspired Home
Price:R4,879 ZAR / night
Paradise in Summerland Key Cove
Entire house
Paradise in Summerland Key Cove
Price:R2,878 ZAR / night
Our home is your home Key West Dreaming!
Entire house
Our home is your home Key West Dreaming!
Price:R3,204 ZAR / night
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Price:R5,451 ZAR / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
Price:R7,283 ZAR / night
Work or Home School from Paradise
SUPERHOSTEntire house
Work or Home School from Paradise
Price:R6,700 ZAR / night
Casa Cristol - Family Friendly Classic KW Charm
SUPERHOSTEntire house
Casa Cristol - Family Friendly Classic KW Charm
Price:R8,142 ZAR / night
Living the dream!
Entire house
Living the dream!
Price:R3,426 ZAR / night
Duval Delight
Entire house
Duval Delight
Price:R4,003 ZAR / night

Houses with pools

Sunrise Beach Escape
SUPERHOSTEntire house
Sunrise Beach Escape
Price:R4,264 ZAR / night
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Price:R3,574 ZAR / night
Palm Breezes! Room for Everyone on the Ocean.
SUPERHOSTEntire house
Palm Breezes! Room for Everyone on the Ocean.
Price:R6,841 ZAR / night
Daisy Space on a Cudjoe Key Canal
SUPERHOSTEntire house
Daisy Space on a Cudjoe Key Canal
Price:R2,871 ZAR / night
Newly Renovated Oceanside House with Pool
SUPERHOSTEntire house
Newly Renovated Oceanside House with Pool
Price:R4,518 ZAR / night
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
Entire house
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
Price:R2,443 ZAR / night
Plant-filled home with private pool and great central location!
Entire house
Plant-filled home with private pool and great central location!
Price:R1,803 ZAR / night
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOSTEntire house
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
Price:R7,279 ZAR / night
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOSTEntire house
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Price:R5,234 ZAR / night
Heart of KW, Resort  RENOVATED, private pool wifi.
SUPERHOSTEntire house
Heart of KW, Resort RENOVATED, private pool wifi.
Price:R7,538 ZAR / night
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
SUPERHOSTEntire house
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
Price:R16,900 ZAR / night
Forever Gem in Key West with Swimming Pool
Entire house
Forever Gem in Key West with Swimming Pool
Price:R8,756 ZAR / night

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