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

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

Located 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.

What guests are saying:

“Joe's place is incredible! A great location close enough to everything yet a quiet and private feeling patio area. It's about a 20ish minute walk to town which we did many times. This is an extremely cozy and relaxing place to stay for two people, definitely not more. Awesome suggestions for local food and activities and great hospitality all around. I hope to come back here to stay again.”

Work or Home School from Paradise
SUPERHOSTEntire house · 8 guests · 4 beds · 3 baths
Work or Home School from Paradise

As we face school closures and shift toward remote work, why not choose to do it from paradise? This family-friendly home offers fast wifi, a comfortable workspace, and/or is suitable for children.

What guests are saying:

“We were lucky enough to snag this place for the month of October and we could not have been more pleased! Plenty of room for multiple couples and the location was perfect. Romi and Shawn were very helpful during our stay and very responsive to any questions we had along the way. In my opinion this is THE place to stay in Key West and we hope to be back for our next trip to the Keys!”

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:$256 / night
Duval Balcony - Suite Mischief
SUPERHOSTEntire apartment
Duval Balcony - Suite Mischief
Price:$170 / night
Duval Street Duplex w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Duplex w/ Balcony and Parking
Price:$378 / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Price:$255 / night
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
Price:$200 / night
Key West - Sunrise ❀ The Green House
SUPERHOSTEntire apartment
Key West - Sunrise ❀ The Green House
Price:$184 / night
Duval Balcony - Street Suite
SUPERHOSTEntire apartment
Duval Balcony - Street Suite
Price:$175 / night
Bella Vita - 1B/1B Condo Just Steps from Duval
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Bella Vita - 1B/1B Condo Just Steps from Duval
Price:$215 / night
The Bartlum
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The Bartlum
Price:$206 / night
Historic Caroline St. Apartment 1
Entire apartment
Historic Caroline St. Apartment 1
Price:$167 / night
Duval Street Apartment w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Apartment w/ Balcony and Parking
Price:$218 / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
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KW Luxury 2/2 Beachfront resort Tropical Oasis
Price:$344 / night
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Pet-friendly houses

Pet Friendly Monthly Key West Rental
Entire house
Pet Friendly Monthly Key West Rental
Price:$350 / night
Dog-friendly home in Old Town - walk to shops, restaurants, & more
Entire house
Dog-friendly home in Old Town - walk to shops, restaurants, & more
Price:$140 / 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:$494 / night
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
Entire house
Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool
Price:$783 / night
Paradise in Summerland Key Cove
Entire house
Paradise in Summerland Key Cove
Price:$189 / night
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!
Price:$684 / 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:$349 / night
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Price:$358 / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
Price:$672 / night
Casa Cristol - Family Friendly Classic KW Charm
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Casa Cristol - Family Friendly Classic KW Charm
Price:$535 / night
Living the dream!
Entire house
Living the dream!
Price:$225 / night
Duval Delight
Entire house
Duval Delight
Price:$248 / night
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Houses with pools

Sunrise Beach Escape
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Sunrise Beach Escape
Price:$280 / night
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Price:$250 / night
Palm Breezes! Room for Everyone on the Ocean.
SUPERHOSTEntire house
Palm Breezes! Room for Everyone on the Ocean.
Price:$449 / night
Bring Your Boat! 2 BR/2BA Waterfront Paradise!
SUPERHOSTEntire house
Bring Your Boat! 2 BR/2BA Waterfront Paradise!
Price:$225 / night
Newly Renovated Oceanside House with Pool
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Newly Renovated Oceanside House with Pool
Price:$293 / night
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Entire house
WATERFRONT PARADISE AT VENTURE OUT+ BIKES & KAYAKS
Price:$218 / night
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
SUPERHOSTEntire house
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
Price:$184 / night
Plant-filled home with private pool and great central location!
Entire house
Plant-filled home with private pool and great central location!
Price:$134 / night
Heart of KW, Resort  RENOVATED, private pool wifi.
SUPERHOSTEntire house
Heart of KW, Resort RENOVATED, private pool wifi.
Price:$524 / 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:$1,110 / night
Forever Gem in Key West with Swimming Pool
Entire house
Forever Gem in Key West with Swimming Pool
Price:$575 / night
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
SUPERHOSTEntire house
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
Price:$378 / night
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Nearby destinations