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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
SUPERHOST
  1. Entire apartment
  2. Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
SUPERHOST
  1. Entire apartment
  2. Key West
Duval Street Duplex w/ Balcony and Parking
SUPERHOST
  1. Entire apartment
  2. Key West
Island Color Suite
  1. Entire apartment
  2. Key West
Key West - Sunrise ❀ The Green House
SUPERHOST
  1. Entire apartment
  2. Key West
Key West Suites Hotel -Adam Scott Rote Suite #203
  1. Entire apartment
  2. Key West
Key West - Sunset ❀ The Green House
SUPERHOST
  1. Entire apartment
  2. Key West
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOST
  1. Private room
  2. Key West
Mallory House Room #1
SUPERHOST
  1. Entire apartment
  2. Key West
Key west in town studio with free bikes
SUPERHOST
  1. Private room
  2. Key West
The Galleria~Unit 11 -- Recently Remodeled!
  1. Entire apartment
  2. Key West
Luxurious apartment with pool #2

Pet-friendly houses

SUPERHOST
  1. Entire house
  2. Cudjoe Key
Cudjoe Key Home with a View
SUPERHOST
  1. Entire house
  2. Key West
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
SUPERHOST
  1. Entire house
  2. Key West
Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
SUPERHOST
  1. Entire house
  2. Upper Sugarloaf Key
Palms Resort at Sugarloaf / Green House
SUPERHOST
  1. Entire house
  2. Key West
WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
  1. Entire house
  2. Key West
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
SUPERHOST
  1. Entire house
  2. Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
SUPERHOST
  1. Entire house
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
  1. Entire house
  2. Key West
Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
SUPERHOST
  1. Entire house
  2. Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
  1. Entire house
  2. Cudjoe Key
Beautiful & Private Pool with Atlantic Ocean view
  1. Entire house
  2. Key West
Duval Delight

Houses with pools

SUPERHOST
  1. Entire house
  2. Cudjoe Key
Sunrise Beach Escape
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Paradise at Cudjoe Bay
  1. Entire house
  2. Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Erin Go Bronx canal-front mid-rise
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Daisy Space on a Cudjoe Key Canal *Plz read sumry*
  1. Entire house
  2. Cudjoe Key
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
  1. Entire house
  2. Cudjoe Key
Fabulous Florida Keys!
  1. Entire house
  2. Cudjoe Key
Sunrise Supreme Paradise: your 2bdrm2bath vacation
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Erin Go "Spaaagh" canal-front mid-rise
SUPERHOST
  1. Entire house
  2. Key West
Royal Escape
SUPERHOST
  1. Entire house
  2. Key West
Clean and Relaxing! 3 King Suites! With everything
SUPERHOST
  1. Entire house
  2. Key West
Robinson Crusoe Cottage

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