Cottage vacation 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.
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 hot tub
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
Apr. 24 – May 1
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Nov. 30 – Dec. 7
Cottage in Cudjoe Key
4.61 out of 5 average rating, 94 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Nov. 5 – 12
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Nov. 14 – 21
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Oct. 25 – Nov. 1
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
Aug. 30 – Sep. 6
Cottage in Cudjoe Key
4.94 out of 5 average rating, 47 reviewsNAUTILUS...ocean front cottage retreat ~
Jan. 3 – 10
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
Feb. 19 – 26
Pet-friendly cottage rentals
Cottage in Key Largo
4.96 out of 5 average rating, 57 reviews2 BR with private Tiki Boat dock for 25' boat max
Sep. 17 – 24
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
Nov. 30 – Dec. 7
Cottage in Key West
4.73 out of 5 average rating, 127 reviews1BR | Dog Friendly | Deck | Grill | AC
Jul. 15 – 22
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
Oct. 25 – Nov. 1
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
Jul. 24 – 31
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Dec. 6 – 13
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
Oct. 19 – 26
Cottage in Key West
4.82 out of 5 average rating, 17 reviewsColony Sunset- Bright and airy cottage
Oct. 8 – 15
Private cottage rentals
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Dec. 17 – 24
Cottage in Key West
4.74 out of 5 average rating, 338 reviews1 bedroom Cottage
Jul. 30 – Aug. 6
Cottage in Key Largo
5.0 out of 5 average rating, 26 reviewsCottage home in the heart of Key Largo
Jul. 23 – 30
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 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
Nov. 29 – Dec. 6
Cottage in Key Largo
4.67 out of 5 average rating, 3 reviewsVacation spot
Apr. 26 – May 3
Cottage in Marathon
4.27 out of 5 average rating, 11 reviewsOcean Cottage on Unique Private Island
Aug. 30 – Sep. 6
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
$151 CAD before taxes and fees
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