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 Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
1–8 Sep
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
25 Aug – 1 Sep
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
21–28 Sep
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
15–22 Nov
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
22–29 Nov
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
12–19 Nov
Cottage in Cudjoe Key
4.93 out of 5 average rating, 45 reviewsNAUTILUS...ocean front cottage retreat ~
24–31 Oct
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
28 Sep – 5 Oct
Pet-friendly cottage rentals
Cottage in Key Largo
4.96 out of 5 average rating, 56 reviews2 BR with private Tiki Boat dock for 25' boat max
29 Oct – 5 Nov
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
18–25 Nov
Cottage in Key West
4.73 out of 5 average rating, 126 reviews1BR | Dog Friendly | Deck | Grill | AC
17–24 Jul
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
7–14 Oct
Cottage in Key West
5.0 out of 5 average rating, 7 reviewsA Touch of Bermuda in Key West
17–24 Mar
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
6–13 Dec
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
19–26 Oct
Cottage in Key West
4.81 out of 5 average rating, 16 reviewsColony Sunset- Bright and airy cottage
29 Jan – 5 Feb
Private cottage rentals
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
27 Aug – 3 Sep
Cottage in Key West
4.74 out of 5 average rating, 337 reviews1 bedroom Cottage
14–21 Jul
Cottage in Key Largo
5.0 out of 5 average rating, 26 reviewsCottage home in the heart of Key Largo
10–17 Oct
Cottage in Key Largo
5.0 out of 5 average rating, 6 reviewsOcean Shores Cottage: Heated private Pool-OS canal
25 Jan – 1 Feb
Cottage in Islamorada
5.0 out of 5 average rating, 11 reviewsAnglers Reef Islamorada
1–8 Mar
Cottage in Islamorada
4.76 out of 5 average rating, 70 reviewsSerene Cozy Cottage in Islamorada with Heated Pool
30 Oct – 6 Nov
Cottage in Tavernier
4.86 out of 5 average rating, 7 reviewsCozy 2-bedroom in Tavernier - Islamorada, FL Keys
13–20 Apr
Cottage in Key Largo
4.67 out of 5 average rating, 3 reviewsVacation spot
13–20 Mar
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
$185 NZD before taxes and fees
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