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 Key Colony Beach
4.57 out of 5 average rating, 7 reviews2BR dog-friendly water view stay, resort amenities
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, 120 reviewsCalypso Cottage
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Cottage in Cudjoe Key
4.89 out of 5 average rating, 56 reviewsTurtle Cove Views @ Venture Out - Waterfront
Cottage in Cudjoe Key
4.94 out of 5 average rating, 47 reviewsNAUTILUS...ocean front cottage retreat ~
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
Pet-friendly cottage rentals
Cottage in Key Largo
4.96 out of 5 average rating, 57 reviews2 BR with private Tiki Boat dock for 25' boat max
Cottage in Key Largo
4.94 out of 5 average rating, 34 reviewsSpacious cottage in the heart of the keys
Cottage in Key West
4.73 out of 5 average rating, 127 reviews1BR | Dog Friendly | Deck | Grill | AC
Cottage in Marathon
5.0 out of 5 average rating, 4 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 Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Cottage in Key West
4.76 out of 5 average rating, 98 reviewsIsland Style - the only way to vacation!
Private cottage rentals
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Cottage in Key West
4.74 out of 5 average rating, 338 reviews1 bedroom Cottage
Cottage in Key Largo
5.0 out of 5 average rating, 29 reviewsCottage home in the heart of Key Largo
Cottage in Key Largo
5.0 out of 5 average rating, 6 reviewsOcean Shores Cottage: Heated private Pool-OS canal
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 Key Largo
4.67 out of 5 average rating, 3 reviewsLugar para vacacionar
Cottage in Marathon
4.27 out of 5 average rating, 11 reviewsOcean Cottage on Unique Private Island
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
$166 AUD before taxes and fees
Destinations to explore
- Varadero Holiday rentals
- Havana Accommodation & holiday rentals
- Naples Accommodation & holiday rentals
- Miami Holiday rentals
- Miami Beach Accommodation & holiday rentals
- Fort Lauderdale Accommodation & holiday rentals
- Boca Raton Accommodation & holiday rentals
- West Palm Beach Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Accommodation & holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Beachfront rentals Key West
- Kid-friendly rentals Key West
- Pet-friendly rentals Key West
- Fitness-friendly rentals Key West
- Villa rentals Key West
- Rentals with a hot tub Key West
- Waterfront rentals Key West
- Boat rentals Key West
- Townhouse rentals Key West
- Beach condo rentals Key West
- Rentals with a fire pit Key West
- Rentals with a kayak Key West
- Rentals with a washing machine and dryer Key West
- Monthly Rentals Key West
- Family-friendly rentals Key West
- Mansion rentals Key West
- Apartment rentals Key West
- Bungalow rentals Key West
- Rentals with pools Key West
- Rentals with a patio Key West
- Rentals with outdoor seating Key West
- House rentals Key West
- Rentals with beach access Key West
- Rentals with an EV charger Key West
- Beach house rentals Key West
- Rentals with an accessible height toilet Key West
- Condo rentals Key West
- Rentals with breakfast 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