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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.

Sunrise Beach Escape
SUPERHOST
Entire house · 6 guests · 2 beds · 3 baths

Sunrise Beach EscapeFor your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

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

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  2. Key West
Studio suite w/ shared hot tubs, patio, kitchenette - steps from beach. Dogs OK!
R2,058 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
R5,570 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Stock Island
Studio Apartment in Friendly Marina
R2,061 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Conch Life Condo
R5,827 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Studio Blu
R3,705 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Old Town Studio Apartment • Walk Everywhere!
R1,816 ZAR per night
  1. Entire apartment
  2. Key West
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!
R5,176 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Bella Vita - 1B/1B Condo Just Steps from Duval
R3,784 ZAR per night
  1. Entire apartment
  2. Key West
Studio condo w/ entertainment, full kitchen & private parking - central location
R2,134 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
Historic Caroline St. Apartment 1
R2,528 ZAR per night
SUPERHOST
  1. Entire apartment
  2. Key West
KW Luxury 2/2 Beachfront resort Tropical Oasis
R6,861 ZAR per night
SUPERHOST
  1. Private room
  2. Key West
Mallory House Room #2
R2,951 ZAR per night

Pet-friendly houses

SUPERHOST
  1. Entire house
  2. Key West
Big Blu - 5 bedroom, 4 bath in old town
R10,837 ZAR per night
  1. Entire house
  2. Key West
Pet Friendly Monthly Key West Rental
R5,297 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Clean and Bright Key West Inspired Home
R4,525 ZAR per night
  1. Entire house
  2. Key West
Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
R11,851 ZAR per night
  1. Entire house
  2. Key West
Dog-friendly home in Old Town - walk to shops, restaurants, & more
R1,922 ZAR per night
No reviews yet
  1. Entire house
  2. Summerland Key
Wonderful, pet friendly home for rent with direct (no bridge) access to Atlantic
R2,376 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
R5,418 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
R5,418 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Royal Escape
R14,757 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Blu on White - Work or Home School from Paradise!
R8,324 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Casa Cristol - Family Friendly Classic KW Charm
R8,484 ZAR per night
  1. Entire house
  2. Key West
Living the dream!
R3,405 ZAR per night

Houses with pools

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  2. Key West
The Palm Villa, Island Oasis steps from Duval
R10,541 ZAR per night
  1. Entire house
  2. Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
R4,071 ZAR per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
R7,367 ZAR per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Daisy Space on a Cudjoe Key Canal
R3,723 ZAR per night
No reviews yet
  1. Entire house
  2. Key West
Trendy dog-friendly family home w/ gas grill, outdoor shower, and private pool!
R3,981 ZAR per night
SUPERHOST
  1. Entire house
  2. Cudjoe Key
Newly Renovated Oceanside House with Pool
R4,389 ZAR per night
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  2. Key West
Gorgeous home w/lush patio & private pool-two blocks to Higgs Beach
R3,875 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Heart of KW, Resort RENOVATED, private pool wifi.
R15,574 ZAR per night
SUPERHOST
  1. Entire house
  2. Key West
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
R21,931 ZAR per night
  1. Entire house
  2. Key West
Forever Gem in Key West with outdoor Swimming Pool
R8,703 ZAR per night
  1. Entire house
  2. Key West
Angela’s Cottage/Private Pool/Pets Welcome/OldTown
R6,205 ZAR per night
  1. Entire house
  2. Key West
Clean and Relaxing! 3 King Suites! With everything
R6,433 ZAR per night

Nearby destinations