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.

Guest favourite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
18–25 JulIndividual Host,
€ 532 per night
4.94 out of 5 average rating, 265 reviews
Guest favourite
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.
1–8 DecIndividual Host,
€ 329 per night
4.97 out of 5 average rating, 437 reviews
Superhost
Houseboat in Key West
Happys Houseboat
This beautiful houseboat is nestled in a calm protected bay, it has hot water, a fridge and Air Conditioning! This boat was featured in Old Dominion‘s music video “I was on a boat that day”. Beautiful sites all around to wake up on the water and sunsets and stars to experiences as you relax on the top deck in the evening. Included in the rental is use of a skiff to get to and from land and and a seventh generation local captain to assist in check in and give a tour of the Houseboat.
6–13 NovIndividual Host,
€ 440 per night
4.85 out of 5 average rating, 161 reviews

Popular amenities for Key West holiday rentals

Stay near Key West's top sights

Duval Street62 locals recommend
Mallory Square100 locals recommend
Key West Butterfly and Nature Conservatory56 locals recommend
Fort Zachary Taylor Historic State Park47 locals recommend
Higgs Beach21 locals recommend
Sebago Watersports6 locals recommend

Other great holiday rentals in Key West

Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
21–28 JanIndividual Host,
€ 426 per night
4.88 out of 5 average rating, 215 reviews
Guest favourite
Flat in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
3–10 JulIndividual Host,
€ 687 per night
4.97 out of 5 average rating, 230 reviews
Guest favourite
Apartment in Key West
A Perfect Getaway
23–30 JunIndividual Host,
€ 519 per night
4.85 out of 5 average rating, 119 reviews
Superhost
Flat in Key West
The Bartlum | Luxury Studio In Prime Location!
11–18 AugProfessional Host,
€ 542 per night
4.84 out of 5 average rating, 208 reviews
Guest favourite
Houseboat in Key West
Key West Luxury Houseboat
30 Jul – 6 AugProfessional Host,
€ 708 per night
4.92 out of 5 average rating, 183 reviews
Guest favourite
Flat in Key West
Studio Blu - Key West, FL - Hip Studio in Old Town
31 Jan – 7 FebIndividual Host,
€ 337 per night
4.94 out of 5 average rating, 354 reviews
Guest favourite
Townhouse in Key West
Stunning Townhouse * Full kitchen! * Sleeps 6
30 Oct – 6 NovProfessional Host,
€ 678 per night
4.96 out of 5 average rating, 220 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
14–21 DecIndividual Host,
€ 511 per night
4.96 out of 5 average rating, 26 reviews
Guest favourite
Apartment in Key West
Hidden Beach unit 1 The Perfect Place to stay
21–28 NovIndividual Host,
€ 602 per night
4.96 out of 5 average rating, 76 reviews
Superhost
Apartment in Key West
Ocean Front Studio private Sandy Beach in Key West
25 Jan – 1 FebIndividual Host,
€ 323 per night
4.89 out of 5 average rating, 72 reviews
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
19–26 JanIndividual Host,
€ 951 per night
4.84 out of 5 average rating, 38 reviews
Guest favourite
Bungalow in Key West
Atlantis House's Palm Suite-voted top 25 in USA
14–21 AugIndividual Host,
€ 659 per night
4.99 out of 5 average rating, 71 reviews

Quick stats about holiday rentals in Key West

Total rentals

1.8K properties

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

490 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

52K reviews

Nightly prices starting at

€ 9 before taxes and fees

Destinations to explore

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