Cottage vacation 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.
Vacation 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 pool
Cottage in Key West
4.6 out of 5 average rating, 10 reviewsAnn Street Tranquility
Cottage in Key West
4.71 out of 5 average rating, 7 reviewsAnn Street Cottage
Cottage in Key West
4.71 out of 5 average rating, 14 reviewsColony Poolside: A charming bungalow near Duval
Cottage in Key West
4.67 out of 5 average rating, 3 reviewsPete's Cottages: Twin Cypress cottages steps from
Cottage in Key West
4.69 out of 5 average rating, 85 reviewsStay at Hidden Treasure for a relaxing vacation!
Cottage in Key West
5 out of 5 average rating, 23 reviewsPete's West Cottage steps from Duval
Cottage in Islamorada
5 out of 5 average rating, 12 reviewsAnglers Reef Islamorada
Cottage in Key West
4.8 out of 5 average rating, 15 reviewsPete's East Cottage: Cypress east cottage steps
Cottage rentals with a hot tub
Cottage in Cudjoe Key
4.9 out of 5 average rating, 60 reviewsTurtle Cove Views at Venture Out
Cottage in Cudjoe Key
4.84 out of 5 average rating, 93 reviewsOCEANIA... water front cottage retreat ~
Cottage in Cudjoe Key
4.64 out of 5 average rating, 106 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Cottage in Cudjoe Key
4.71 out of 5 average rating, 133 reviewsCalypso Cottage
Cottage in Key West
4.78 out of 5 average rating, 27 reviewsDarling of Duval at Old Town
Cottage in Cudjoe Key
New place to stayCozy, Perfect Conch Cottage! - VO315
Cottage in Cudjoe Key
4.94 out of 5 average rating, 54 reviewsNAUTILUS...ocean front cottage retreat ~
Cottage in Key Colony Beach
4.57 out of 5 average rating, 7 reviews2BR dog-friendly water view stay, resort amenities
Pet-friendly cottage rentals
Cottage in Key West
4.83 out of 5 average rating, 18 reviewsColony Sunset- Bright and airy cottage
Cottage in Key West
5 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Cottage in Key West
4.84 out of 5 average rating, 77 reviewsHidden Oasis @ the Colony ~ Great location
Cottage in Islamorada
New place to stayCottage on Bayfront Estate – Pool, Beach, & Dock
Cottage in Islamorada
4.82 out of 5 average rating, 164 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Cottage in Key Colony Beach
5 out of 5 average rating, 10 reviewsLuxurious Oasis: 2BR w/Pool, Tiki, Dock & Beach
Cottage in Islamorada
4.84 out of 5 average rating, 147 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Cottage in Marathon
5 out of 5 average rating, 8 reviewsWaterview 1B/1B Tiny Home
Quick stats about cottage rentals in Key West
Total rentals
40 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
20 properties have a pool
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