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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
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.

Pet Friendly Monthly Key West Rental
Entire house · 6 guests · 3 beds · 2 baths

Pet Friendly Monthly Key West RentalLush tropical grounds greet you upon entrance of this enhanced 3/2. This adorable retreat is located in what locals call “Mid Town” offering a true local’s experience and plenty of quiet time away from your hustle and bustle. Just minutes away from the beaches and ocean boulevard that have the best views of the sunrise. Only 2 miles from Duval Street but just far enough away to have some peace and quiet.

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

1 bedroom Cottage
SUPERHOSTEntire apartment
1 bedroom Cottage
Price:$278 / night
Cute, Convenient, Oldtown, Parking
SUPERHOSTEntire apartment
Cute, Convenient, Oldtown, Parking
Price:$155 / night
Duval Street Duplex w/ Balcony and Parking
SUPERHOSTEntire apartment
Duval Street Duplex w/ Balcony and Parking
Price:$498 / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
Price:$307 / night
Old Town Studio Apartment • Walk Everywhere!
SUPERHOSTEntire apartment
Old Town Studio Apartment • Walk Everywhere!
Price:$120 / night
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
Price:$250 / night
Duval Balcony Spanky's Retreat
SUPERHOSTEntire apartment
Duval Balcony Spanky's Retreat
Price:$179 / night
Historic Caroline St. Apartment 1
SUPERHOSTEntire apartment
Historic Caroline St. Apartment 1
Price:$167 / night
Location, Location, Location! Cute and Convenient!
Entire apartment
Location, Location, Location! Cute and Convenient!
Price:$93 / night
Happy Harbor Walk Apartment • Old Town
SUPERHOSTEntire apartment
Happy Harbor Walk Apartment • Old Town
Price:$185 / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
Price:$335 / night
Mallory House Room #2
SUPERHOSTPrivate room
Mallory House Room #2
Price:$156 / night

Pet-friendly houses

**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Entire house
**CAPTAIN'S CHOICE** ISLAND RETREAT IN OLD TOWN!
Price:$225 / night
Lennon's Lodge, Luxury Accommodations for up to 6!
SUPERHOSTEntire house
Lennon's Lodge, Luxury Accommodations for up to 6!
Price:$488 / night
Clean and Bright Key West Inspired Home
SUPERHOSTEntire house
Clean and Bright Key West Inspired Home
Price:$299 / 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:$137 / 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:$358 / night
Live Like a Local in this Key West Conch Cottage
Entire house
Live Like a Local in this Key West Conch Cottage
Price:$112 / 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:$975 / night
Work or Home School from Paradise
SUPERHOSTEntire house
Work or Home School from Paradise
Price:$496 / night
Casa Cristol - Family Friendly Classic KW Charm
SUPERHOSTEntire house
Casa Cristol - Family Friendly Classic KW Charm
Price:$549 / night
Living the dream!
Entire house
Living the dream!
Price:$225 / night
Duval Delight
Entire house
Duval Delight
Price:$375 / night

Houses with pools

Sunrise Beach Escape
SUPERHOSTEntire house
Sunrise Beach Escape
Price:$280 / night
Pink Beach Paradise
SUPERHOSTEntire house
Pink Beach Paradise
Price:$625 / night
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Price:$269 / night
Club Riviera House on Water IN KEY WEST
SUPERHOSTEntire house
Club Riviera House on Water IN KEY WEST
Price:$300 / night
Oceanfront House
Entire house
Oceanfront House
Price:$417 / 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
SUPERHOSTEntire house
Newly Renovated Oceanside House with Pool
Price:$291 / night
Paradise in Summerland Key Cove
Entire house
Paradise in Summerland Key Cove
Price:$189 / night
Heart of KW, Resort  RENOVATED, private pool wifi.
SUPERHOSTEntire house
Heart of KW, Resort RENOVATED, private pool wifi.
Price:$583 / night
Keys Pool Home, minutes from Key West
Entire house
Keys Pool Home, minutes from Key West
Price:$225 / night
Clean and Relaxing! 3 King Suites! With everything
Entire house
Clean and Relaxing! 3 King Suites! With everything
Price:$425 / night

Nearby destinations