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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.

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 down 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.

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.

Living the dream!
Entire house · 4 guests · 2 beds · 2 baths

Living the dream!Our beautiful home is located in Key Haven on a canal for easy boating access. We are just minutes away from all the best Key West has to offer. We have a master bedroom and large master bath with double vanity and cable TV. A guest bedroom with full size bed with large closet and cable TV. Additional full bath. Large gourmet kitchen. Living area and entertainment room. Our back yard is a little slice of paradise. In ground pool, Jacuzzi with lots of seating for outdoor entertaining. Gas grill.

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

Studio suite w/ shared hot tubs, patio, kitchenette - steps from beach. Dogs OK!
Entire apartment
Studio suite w/ shared hot tubs, patio, kitchenette - steps from beach. Dogs OK!
$134 / night
Studio Apartment in Friendly Marina
SUPERHOSTEntire apartment
Studio Apartment in Friendly Marina
$136 / night
Conch Life Condo
SUPERHOSTEntire apartment
Conch Life Condo
$385 / night
Studio Blu
SUPERHOSTEntire apartment
Studio Blu
$249 / night
Old Town Studio Apartment • Walk Everywhere!
SUPERHOSTEntire apartment
Old Town Studio Apartment • Walk Everywhere!
$120 / night
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!
Entire apartment
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis!
$344 / night
Bella Vita - 1B/1B Condo Just Steps from Duval
SUPERHOSTEntire apartment
Bella Vita - 1B/1B Condo Just Steps from Duval
$250 / night
Studio condo w/ entertainment, full kitchen & private parking - central location
Entire apartment
Studio condo w/ entertainment, full kitchen & private parking - central location
$140 / night
Location, Location, Location! Cute and Convenient!
Entire apartment
Location, Location, Location! Cute and Convenient!
$110 / night
Historic Caroline St. Apartment 1
SUPERHOSTEntire apartment
Historic Caroline St. Apartment 1
$167 / night
KW Luxury 2/2 Beachfront resort  Tropical Oasis
SUPERHOSTEntire apartment
KW Luxury 2/2 Beachfront resort Tropical Oasis
$473 / night
Mallory House Room #2
SUPERHOSTPrivate room
Mallory House Room #2
$195 / night

Pet-friendly houses

Cudjoe Key Home with a View
Entire house
Cudjoe Key Home with a View
$280 / night
Big Blu - 5 bedroom, 4 bath in old town
SUPERHOSTEntire house
Big Blu - 5 bedroom, 4 bath in old town
$716 / night
Clean and Bright Key West Inspired Home
SUPERHOSTEntire house
Clean and Bright Key West Inspired Home
$299 / night
The Eagle’s Nest (Sleeps 4 w/ heated pool)
SUPERHOSTEntire house
The Eagle’s Nest (Sleeps 4 w/ heated pool)
$206 / 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
$127 / night
BRAND NEW WATERFRONT 3/2
Entire house
BRAND NEW WATERFRONT 3/2
$180 / 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!
$358 / night
Live Like a Local in this Key West Conch Cottage
Entire house
Live Like a Local in this Key West Conch Cottage
$112 / night
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
SUPERHOSTEntire house
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$358 / night
Royal Escape
SUPERHOSTEntire house
Royal Escape
$975 / night
Angela’s Cottage/Private Pool/Pets Welcome/OldTown
Entire house
Angela’s Cottage/Private Pool/Pets Welcome/OldTown
$410 / night
Casa Cristol - Family Friendly Classic KW Charm
SUPERHOSTEntire house
Casa Cristol - Family Friendly Classic KW Charm
$568 / night

Houses with pools

Sunrise Beach Escape
SUPERHOSTEntire house
Sunrise Beach Escape
$280 / night
Key West, Home, Pool and Electric Car!
Entire house
Key West, Home, Pool and Electric Car!
$132 / night
The Palm Villa, Island Oasis steps from Duval
Entire house
The Palm Villa, Island Oasis steps from Duval
$696 / night
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
Entire house
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
$269 / night
Old Town - Room Opens to Private Pool and Garden
SUPERHOSTPrivate room
Old Town - Room Opens to Private Pool and Garden
$239 / night
Palm Breezes! Room for Everyone on the Ocean.
SUPERHOSTEntire house
Palm Breezes! Room for Everyone on the Ocean.
$487 / night
Sunshine Daydream: Private Home -Old Town Key West
Entire house
Sunshine Daydream: Private Home -Old Town Key West
$550 / night
Daisy Space on a Cudjoe Key Canal
SUPERHOSTEntire house
Daisy Space on a Cudjoe Key Canal
$246 / night
Newly Renovated Oceanside House with Pool
SUPERHOSTEntire house
Newly Renovated Oceanside House with Pool
$290 / night
Heart of KW, Resort  RENOVATED, private pool wifi.
SUPERHOSTEntire house
Heart of KW, Resort RENOVATED, private pool wifi.
$1,029 / night
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
SUPERHOSTEntire house
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
$379 / night
Clean and Relaxing! 3 King Suites! With everything
Entire house
Clean and Relaxing! 3 King Suites! With everything
$425 / night

Nearby destinations