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 Largo
4.96 out of 5 average rating, 56 reviews2 BR with private Tiki Boat dock for 25' boat max
Nov 24 – Dec 1
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
Jan 18 – 25
Cottage in Key Largo
5.0 out of 5 average rating, 6 reviewsOcean Shores Cottage: Heated private Pool-OS canal
Jan 25 – Feb 1
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
Feb 20 – 27
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Oct 7 – 14
Cottage in Islamorada
5.0 out of 5 average rating, 11 reviewsAnglers Reef Islamorada
Mar 1 – 8
Cottage in Islamorada
4.76 out of 5 average rating, 70 reviewsSerene Cozy Cottage in Islamorada with Heated Pool
Jan 27 – Feb 3
Cottage in Key Largo
4.67 out of 5 average rating, 3 reviewsVacation spot
Apr 20 – 27
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
Jul 8 – 15
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Sep 17 – 24
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Dec 15 – 22
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Dec 13 – 20
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Nov 22 – 29
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
Jan 2 – 9
Cottage in Cudjoe Key
4.93 out of 5 average rating, 45 reviewsNAUTILUS...ocean front cottage retreat ~
Oct 27 – Nov 3
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
Oct 10 – 17
Cottage rentals with free parking
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Dec 13 – 20
Cottage in Key Largo
5.0 out of 5 average rating, 26 reviewsCottage home in the heart of Key Largo
Mar 29 – Apr 5
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
Oct 19 – 26
Cottage in Marathon
4.6 out of 5 average rating, 228 reviewsTropical Cottages - Cottage # 8
Aug 18 – 25
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Dec 6 – 13
Cottage in Marathon
4.27 out of 5 average rating, 11 reviewsOcean Cottage on Unique Private Island
Mar 26 – Apr 2
Cottage in Islamorada
4.84 out of 5 average rating, 128 reviewsFLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Mar 8 – 15
Cottage in Islamorada
4.81 out of 5 average rating, 143 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Mar 17 – 24
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
$110 before taxes and fees
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