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, 57 reviews2 BR with private Tiki Boat dock for 25' boat max
Apr 15 – 22
Cottage in Key Largo
4.94 out of 5 average rating, 34 reviewsSpacious cottage in the heart of the keys
Sep 29 – Oct 6
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
Oct 25 – Nov 1
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 Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Nov 11 – 18
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
Mar 13 – 20
Cottage in Key Largo
4.67 out of 5 average rating, 3 reviewsVacation spot
Mar 31 – Apr 7
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
Dec 4 – 11
Cottage in Cudjoe Key
4.61 out of 5 average rating, 94 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jan 2 – 9
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Sep 23 – 30
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Aug 16 – 23
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Jun 21 – 28
Cottage in Cudjoe Key
4.94 out of 5 average rating, 47 reviewsNAUTILUS...ocean front cottage retreat ~
Apr 3 – 10
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
Sep 1 – 8
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
Sep 11 – 18
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
Oct 29 – Nov 5
Cottage in Key Largo
5.0 out of 5 average rating, 29 reviewsCottage home in the heart of Key Largo
Jan 20 – 27
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
Dec 16 – 23
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 31 – Apr 7
Place to stay in Key Largo
4.56 out of 5 average rating, 641 reviewsCottage Sunroom Waterfront Retreat 2 ppl
Aug 14 – 21
Cottage in Islamorada
4.84 out of 5 average rating, 128 reviewsFLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Nov 10 – 17
Cottage in Islamorada
4.81 out of 5 average rating, 143 reviewsFLOATING 1BD 1BA PRIVATE COTTAGE - MAKO
Nov 21 – 28
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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