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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.

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.

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

Cute, Convenient, Oldtown, Parking
SUPERHOSTEntire apartment
Cute, Convenient, Oldtown, Parking
Duval Street Duplex w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Duplex w/ Balcony and Parking
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
Old Town Studio Apartment • Walk Everywhere!
SUPERHOSTEntire apartment
Old Town Studio Apartment • Walk Everywhere!
Key West - Sunrise ❀ The Green House
SUPERHOSTEntire apartment
Key West - Sunrise ❀ The Green House
Key West - Sunset ❀ The Green House
SUPERHOSTEntire apartment
Key West - Sunset ❀ The Green House
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
Historic Caroline St. Apartment 1
SUPERHOSTEntire apartment
Historic Caroline St. Apartment 1
Location, Location, Location! Cute and Convenient!
Entire apartment
Location, Location, Location! Cute and Convenient!
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
Mallory House Room #2
SUPERHOSTPrivate room
Mallory House Room #2

Pet-friendly houses

Pet Friendly Monthly Key West Rental
Entire house
Pet Friendly Monthly Key West Rental
**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Entire house
**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Dog-friendly home in Old Town - walk to shops, restaurants, & more
Entire house
Dog-friendly home in Old Town - walk to shops, restaurants, & more
Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
Entire house
Family-friendly home w/ private pool, furnished patio, and parking - Dogs OK!
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
SUPERHOSTEntire house
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Live Like a Local in this Key West Conch Cottage
Entire house
Live Like a Local in this Key West Conch Cottage
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Royal Escape
SUPERHOSTEntire house
Royal Escape
Work or Home School from Paradise
SUPERHOSTEntire house
Work or Home School from Paradise
Casa Cristol - Family Friendly Classic KW Charm
SUPERHOSTEntire house
Casa Cristol - Family Friendly Classic KW Charm
Living the dream!
Entire house
Living the dream!
Duval Delight
Entire house
Duval Delight

Houses with pools

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Club Riviera House on Water IN KEY WEST
SUPERHOSTEntire house
Club Riviera House on Water IN KEY WEST
Oceanfront House
Entire house
Oceanfront House
Palm Breezes! Room for Everyone on the Ocean.
SUPERHOSTEntire house
Palm Breezes! Room for Everyone on the Ocean.
Bring Your Boat! 2 BR/2BA Waterfront Paradise!
SUPERHOSTEntire house
Bring Your Boat! 2 BR/2BA Waterfront Paradise!
Daisy Space on a Cudjoe Key Canal
SUPERHOSTEntire house
Daisy Space on a Cudjoe Key Canal
Newly Renovated Oceanside House with Pool
SUPERHOSTEntire house
Newly Renovated Oceanside House with Pool
Inviting home near the ocean w/private outdoor pool, deck, and gas grill
Entire house
Inviting home near the ocean w/private outdoor pool, deck, and gas grill
Plant-filled home with private pool and great central location!
Entire house
Plant-filled home with private pool and great central location!
Heart of KW, Resort  RENOVATED, private pool wifi.
SUPERHOSTEntire house
Heart of KW, Resort RENOVATED, private pool wifi.
Keys Pool Home, minutes from Key West
Entire house
Keys Pool Home, minutes from Key West
Clean and Relaxing! 3 King Suites! With everything
Entire house
Clean and Relaxing! 3 King Suites! With everything

Nearby destinations