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Holiday rentals in Key West

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Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
Individual Host
Superhost
Flat in Key West
Key West - Sunset ❀ The Green House
Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!
Professional Host
Superhost
Flat in Key West
Honeymoon Hideaway, King bed, Private Deck & Spa!
Pale blue interiors, small efficiency kitchen, platform Pottery Barn King memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bose Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!
Individual Host

Stay near Key West's top sights

Mallory Square100 locals recommend
Southernmost Point of the Continental US64 locals recommend
The Ernest Hemingway Home and Museum105 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend

Other great holiday rentals in Key West

Superhost
Flat in Key West
Duval St Apartment w/ Balcony w/parking Adult Only
Professional Host
Superhost
Flat in Key West
Studio Blu - Key West, FL - Hip Studio in Old Town
Individual Host
Superhost
Flat in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
Individual Host
Superhost
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
Superhost
Flat in Key West
Duval Balcony - Street Suite
Individual Host
Superhost
Apartment in Key West
Large 2/2 Waterfront Condo Great View Pool & Dock
Individual Host
Superhost
Flat in Key West
The Bartlum by Brightwild | Luxurious Studio
Professional Host
Superhost
Townhouse in Key West
Poolside Cottage #412
Professional Host
Superhost
Apartment in Key West
La Dolce Vita, Old Town Steps to Duval! 3 blks bch
Individual Host
Superhost
Apartment in Key Colony Beach
Oceanfront Breeze Condo Stunning Views, Beach/Pool
Professional Host
Superhost
Apartment in Key West
Hidden Beach unit 2, The Perfect Place To Stay
Individual Host
Superhost
Flat in Key West
Duval Street Suites full kitchen, parking, pool

Quick stats about holiday rentals in Key West

Total rentals

1.7K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

470 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

48K reviews

Nightly prices starting at

£8 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Key West