Cottage holiday rentals in Key West
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Key West
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Key West
Cottage rentals with a hot tub
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Cottage in Cudjoe Key
4.61 out of 5 average rating, 94 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Cottage in Key West
4.82 out of 5 average rating, 22 reviewsDarling of Duval @ Old Town - Adorable Cottage
Cottage in Cudjoe Key
4.94 out of 5 average rating, 47 reviewsNAUTILUS...ocean front cottage retreat ~
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
Pet-friendly cottage rentals
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Cottage in Key West
4.82 out of 5 average rating, 17 reviewsColony Sunset- Bright and airy cottage
Cottage in Marathon
4.6 out of 5 average rating, 228 reviewsTropical Cottages - Cottage # 8
Cottage in Marathon
4.61 out of 5 average rating, 109 reviewsTropical Cottages - Cottage # 10
Cottage in Marathon
4.43 out of 5 average rating, 213 reviewsTropical Cottages - Cottage # 03
Cottage in Marathon
Waterview 1B/1B Tiny Home
Private cottage rentals
Cottage in Islamorada
5.0 out of 5 average rating, 11 reviewsAnglers Reef Islamorada
Cottage in Islamorada
4.76 out of 5 average rating, 70 reviewsSerene Cozy Cottage in Islamorada with Heated Pool
Cottage in Marathon
4.27 out of 5 average rating, 11 reviewsOcean Cottage on Unique Private Island
Cottage in Islamorada
4.84 out of 5 average rating, 128 reviewsFLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Cottage in Islamorada
4.81 out of 5 average rating, 143 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Cottage in Key West
4.67 out of 5 average rating, 12 reviewsBali Hideaway: A studio cottage that's perfect
Cottage in Key West
4.69 out of 5 average rating, 13 reviewsColony Poolside: A charming bungalow near Duval
Cottage in Key West
4.71 out of 5 average rating, 7 reviewsAnn Street Cottage
Quick stats about cottage rentals in Key West
Total rentals
30 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
990 reviews
Nightly prices starting at
€ 102 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
- Villa rentals Key West
- Family-friendly rentals Key West
- Family-friendly rentals Key West
- Rentals with outdoor seating Key West
- Rentals with a firepit Key West
- Rentals with a hot tub Key West
- Rentals with breakfast Key West
- House rentals Key West
- Apartment rentals Key West
- Monthly Rentals Key West
- Waterfront rentals Key West
- Rentals with an accessible-height toilet Key West
- Rentals with beach access Key West
- Pet-friendly rentals Key West
- Beach apartment rentals Key West
- Beachfront rentals Key West
- Townhouse rentals Key West
- Flat rentals Key West
- Bungalow rentals Key West
- Rentals with a kayak Key West
- Rentals with an EV charger Key West
- Rentals with a washing machine and dryer Key West
- Beach house rentals Key West
- Rentals with a patio Key West
- Fitness-friendly rentals Key West
- Rentals with pools Key West
- Mansion rentals Key West
- Cottage rentals Florida
- Cottage rentals Florida Keys
- Cottage rentals Marco Island
- Cottage rentals Monroe County
- 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