Cottage holiday rentals in Key West
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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
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
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
4.6 out of 5 average rating, 96 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Cottage in Cudjoe Key
4.69 out of 5 average rating, 121 reviewsCalypso Cottage
Cottage in Cudjoe Key
4.85 out of 5 average rating, 33 reviewsTidewater 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
4.89 out of 5 average rating, 56 reviewsTurtle Cove Views @ Venture Out - Waterfront
Pet-friendly cottage rentals
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Cottage in Marathon
4.6 out of 5 average rating, 228 reviewsTropical Cottages - Cottage # 8
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!
Cottage in Key West
4.82 out of 5 average rating, 17 reviewsColony Sunset- Bright and airy cottage
Cottage in Key West
4.84 out of 5 average rating, 76 reviewsHidden Oasis @ the Colony ~ Great location
Cottage in Key West
New place to stayThe Southern Cross
Cottage in Marathon
5.0 out of 5 average rating, 5 reviewsWaterview 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
4.25 out of 5 average rating, 12 reviewsOcean Cottage on Unique Private Island
Cottage in Islamorada
4.81 out of 5 average rating, 144 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Cottage in Islamorada
4.85 out of 5 average rating, 131 reviewsFLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Cottage in Key West
4.69 out of 5 average rating, 13 reviewsBali Hideaway: A studio cottage that's perfect
Cottage in Key West
4.65 out of 5 average rating, 23 reviewsOsprey @ Colony
Cottage in Key West
4.73 out of 5 average rating, 11 reviewsPete's East Cottage: Cypress east cottage steps
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
$165 AUD before taxes and fees
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