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
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
Mar 28 – Apr 4
Cottage in Key Largo
5.0 out of 5 average rating, 10 reviewsThe Grand Lodge Right On The Water At Largo Resort
May 12 – 17
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Mar 17 – 24
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 9 – 16
Cottage in Key Largo
4.67 out of 5 average rating, 3 reviewsVacation spot
Mar 13 – 20
Cottage in Key Largo
Coral Reef Cottage
Sep 11 – 18
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
Nov 29 – Dec 6
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Sep 26 – Oct 3
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Sep 21 – 28
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Nov 28 – Dec 5
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
Nov 12 – 19
Cottage in Cudjoe Key
4.93 out of 5 average rating, 45 reviewsNAUTILUS...ocean front cottage retreat ~
Nov 30 – Dec 7
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
Oct 6 – 13
Cottage rentals with free parking
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
Oct 19 – 26
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Dec 6 – 13
Cottage in Tavernier
4.86 out of 5 average rating, 7 reviewsCozy 2-bedroom in Tavernier - Islamorada, FL Keys
Apr 13 – 20
Cottage in Marathon
4.27 out of 5 average rating, 11 reviewsOcean Cottage on Unique Private Island
Oct 3 – 10
Room in Key Largo
4.56 out of 5 average rating, 639 reviewsCottage Sunroom Waterfront Retreat 2 ppl
Aug 12 – 19
Cottage in Islamorada
4.84 out of 5 average rating, 128 reviewsFLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
Aug 27 – Sep 3
Cottage in Islamorada
4.85 out of 5 average rating, 127 reviews1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
Nov 20 – 27
Cottage in Islamorada
5.0 out of 5 average rating, 8 reviewsFloating 2 BD, 1 BATH Private Villa Pirates Lair
Jul 28 – Aug 4
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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