Holiday rentals in Key West
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Key West
Guests agree: these stays are highly rated for location, cleanliness and more.
Home in Key West
4.94 out of 5 average rating, 268 reviewsRomantic 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.
4–11 Aug
Flat in Key West
4.98 out of 5 average rating, 441 reviewsBella 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.
20–27 Jan
Guest suite in Key West
4.83 out of 5 average rating, 12 reviewsConch Republic Studio - Key West Millionaires Row
In the center of prestigious Millionaires Row, Conch Republic Studio is a private, separate rental in the back of the main house with a private entrance. A tranquil getaway for one or a couple in the Historic District. Walk 5 blocks to Duval Street or marina. Only 8 blocks to Hemingway's House and Lighthouse. In the morning enjoy a famous Five Brothers Cuban coffee or sandwich, evenings dine at one of the South's most popular restaurants, Cafe Sole, both just 100 steps away. 1G optic internet!
2–9 Feb
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Key West holiday rentals
Other great holiday rentals in Key West
Cottage in Key West
4.95 out of 5 average rating, 84 reviewsMango Cottage 2 bedroom 2 bath with private pool
1–8 Oct
Home in Key West
5.0 out of 5 average rating, 3 reviewsCharming + Historic Eyebrow Home
24 Feb – 3 Mar
Home in Upper Sugarloaf Key
4.86 out of 5 average rating, 43 reviewsBungalows at Sugarloaf Beach - The Lighthouse
6–13 Aug
Home in Key West
4.95 out of 5 average rating, 39 reviewsSouthard Comfort ~ Feel The Key West Vibe
11–18 Sep
Bungalow in Key West
4.99 out of 5 average rating, 76 reviewsAtlantis House's Palm Suite-voted top 25 in USA
14–21 Oct
Tiny home in Big Pine Key
4.8 out of 5 average rating, 88 reviewsBreezy pines 28 foot 5th wheel trailer .
16–23 Oct
Home in Key West
5.0 out of 5 average rating, 37 reviewsGorgeous Romantic Private Villa, Steps from Duval!
6–13 Mar
Home in Key West
5.0 out of 5 average rating, 13 reviewsVilla Paradiso: A unique mid-town paradise
11–18 May
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
8–15 Jun
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
12–19 Oct
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
9–16 Nov
Flat in Key West
4.93 out of 5 average rating, 15 reviewsOceanfront Condo in Key West
10–17 Jul
Quick stats about holiday rentals in Key West
Total rentals | 1.8T properties |
---|---|
Rentals with a pool | 1.2T properties have a pool |
Pet-friendly rentals | 490 properties allow pets |
Family-friendly rentals | 1.1T properties are a good fit for families |
Total number of reviews | 52T reviews |
Nightly prices starting at | ₹834 before taxes and fees |
Destinations to explore
- Varadero Holiday rentals
- Havana Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Rentals with an EV charger Key West
- Rentals with a washing machine and dryer Key West
- Rentals with a kayak Key West
- Monthly Rentals Key West
- Apartment rentals Key West
- Rentals with pools Key West
- Beach house rentals Key West
- Cottage rentals Key West
- Rentals with a firepit Key West
- Mansion rentals Key West
- Fitness-friendly rentals Key West
- House rentals Key West
- Beach apartment rentals Key West
- Waterfront rentals Key West
- Family-friendly rentals Key West
- Beachfront rentals Key West
- Rentals with outdoor seating Key West
- Rentals with a hot tub Key West
- Rentals with an accessible-height toilet Key West
- Bungalow rentals Key West
- Pet-friendly rentals Key West
- Rentals with breakfast Key West
- Family-friendly rentals Key West
- Cabin rentals Key West
- Townhouse rentals Key West
- Villa rentals Key West
- Rentals with beach access Key West
- Flat rentals Key West
- Rentals with a patio Key West
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom