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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.

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.

Newly Renovated Oceanside House with Pool
SUPERHOST
Entire house · 6 guests · 2 beds · 3 baths

Newly Renovated Oceanside House with PoolThis luxurious home overlooking the Atlantic side is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be s​een from the pool and dock.

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

SUPERHOST
  1. Entire apartment
  2. Key West
Duval Retreat- Contemporary Duval Street Condo
G$84,672 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
G$76,961 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Duval Street Duplex w/ Balcony and Parking
G$188,012 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Island Color Suite
G$67,103 per night
  1. Entire apartment
  2. Key West
Key West - Sunrise ❀ The Green House
G$44,857 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Key West Suites Hotel -Adam Scott Rote Suite #203
G$62,531 per night
  1. Entire apartment
  2. Key West
Key West - Sunset ❀ The Green House
G$42,197 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Bella Vita - 1B/1B Condo Just Steps from Duval
G$52,284 per night
SUPERHOST
  1. Private room
  2. Key West
Mallory House Room #1
G$37,644 per night
SUPERHOST
  1. Entire apartment
  2. Key West
Key west in town studio with free bikes
G$30,624 per night
SUPERHOST
  1. Private room
  2. Key West
The Galleria~Unit 11 -- Recently Remodeled!
G$39,227 per night
  1. Entire apartment
  2. Key West
Luxurious apartment with pool #2
G$73,197 per night

Pet-friendly houses

SUPERHOST
  1. Entire house
  2. Cudjoe Key
Cudjoe Key Home with a View
G$58,558 per night
SUPERHOST
  1. Entire house
  2. Key West
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
G$231,721 per night
SUPERHOST
  1. Entire house
  2. Key West
Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
G$53,777 per night
SUPERHOST
  1. Entire house
  2. Upper Sugarloaf Key
Palms Resort at Sugarloaf / Green House
G$202,143 per night
SUPERHOST
  1. Entire house
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
G$88,882 per night
SUPERHOST
  1. Entire house
  2. Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
G$99,966 per night
  1. Entire house
  2. Key West
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
G$172,118 per night
SUPERHOST
  1. Entire house
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
G$74,870 per night
  1. Entire house
  2. Key West
Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
G$32,625 per night
SUPERHOST
  1. Entire house
  2. Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
G$74,870 per night
  1. Entire house
  2. Cudjoe Key
Beautiful & Private Pool with Atlantic Ocean view
G$94,372 per night
  1. Entire house
  2. Key West
Duval Delight
G$131,177 per night

Houses with pools

SUPERHOST
  1. Entire house
  2. Cudjoe Key
Sunrise Beach Escape
G$58,558 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Paradise at Cudjoe Bay
G$65,877 per night
  1. Entire house
  2. Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
G$56,257 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Erin Go Bronx canal-front mid-rise
G$47,085 per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Daisy Space on a Cudjoe Key Canal *Plz read sumry*
G$53,957 per night
  1. Entire house
  2. Cudjoe Key
Fabulous Florida Keys!
G$44,964 per night
  1. Entire house
  2. Cudjoe Key
Sunrise Supreme Paradise: your 2bdrm2bath vacation
G$44,606 per night
  1. Entire house
  2. Cudjoe Key
OCEAN VIEW PARADISE AT VENTURE OUT + BIKES/KAYAKS
G$49,086 per night
SUPERHOST
  1. Entire house
  2. Key West
Royal Escape
G$203,906 per night
SUPERHOST
  1. Entire house
  2. Key West
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
G$79,172 per night
SUPERHOST
  1. Entire house
  2. Key West
Clean and Relaxing! 3 King Suites! With everything
G$104,567 per night
SUPERHOST
  1. Entire house
  2. Key West
Robinson Crusoe Cottage
G$64,413 per night

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