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 Key West cottage rentals
Cottage rentals with a hot tub
Cottage in Cudjoe Key
Walk to the Pool - Venture Out Unit 333
Cottage in Key Colony Beach
2BR dog-friendly water view stay, resort amenities
Cottage in Cudjoe Key
VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Cottage in Cudjoe Key
Calypso Cottage
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Cottage in Key West
Darling of Duval @ Old Town - Adorable Cottage
Cottage in Cudjoe Key
OCEANIA... water front cottage retreat ~
Cottage in Cudjoe Key
Tidewater Views @ Venture Out - Waterfront
Pet-friendly cottage rentals
Cottage in Marathon
Prime Location 1B/1B Home
Cottage in Key West
A Touch of Bermuda in Key West
Cottage in Marathon
Tropical Cottages - Cottage # 8
Cottage in Islamorada
Ocean Front Cottage
Cottage in Key West
Island Style - the only way to vacation!
Cottage in Key West
Colony Sunset- Bright and airy cottage
Cottage in Key West
The Southern Cross
Cottage in Marathon
Waterview 1B/1B Tiny Home
Private cottage rentals
Cottage in Islamorada
Anglers Reef Islamorada
Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
Cottage in Marathon
Ocean Cottage on Unique Private Island
Cottage in Islamorada
FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Cottage in Islamorada
FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Cottage in Key West
Ann Street Tranquility
Cottage in Key West
Bali Hideaway: A studio cottage that's perfect
Cottage in Key West
Osprey @ Colony
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
$178 NZD 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 accessible height toilet Key West
- Rentals with pools Key West
- Villa rentals Key West
- House rentals Key West
- Fitness-friendly rentals Key West
- Rentals with a fire pit Key West
- Kid-friendly rentals Key West
- Hotel rentals Key West
- Rentals with breakfast Key West
- Waterfront rentals Key West
- Mansion rentals Key West
- Rentals with a hot tub Key West
- Rentals with a washing machine and dryer Key West
- Boat rentals Key West
- Rentals with an EV charger Key West
- Monthly Rentals Key West
- Family-friendly rentals Key West
- Townhouse rentals Key West
- Rentals with beach access Key West
- Rentals with a kayak Key West
- Rentals with an accessible height bed Key West
- Rentals with a patio Key West
- Condo rentals Key West
- Rentals with outdoor seating Key West
- Beach condo rentals Key West
- Pet-friendly rentals Key West
- Beach house rentals Key West
- Beachfront rentals Key West
- Apartment 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