Cottage holiday rentals in Florida Keys
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Top-rated cottage rentals in Florida Keys
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 Florida Keys cottage rentals
Cottage rentals with a hot tub
Cottage in Fort Lauderdale
5.0 out of 5 average rating, 87 reviewsPrivate Couple’s cottage. Hotub. Beach. Miami
21–28 Sep
Cottage in Cudjoe Key
4.91 out of 5 average rating, 79 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
17–24 Oct
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
27 Jul – 3 Aug
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
8–15 Sep
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
8–15 Jul
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
30 Aug – 6 Sep
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
9–16 Aug
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
22–29 Nov
Pet-friendly cottage rentals
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
23–30 Nov
Cottage in Key Largo
4.96 out of 5 average rating, 56 reviews2 BR with private Tiki Boat dock for 25' boat max
26 Mar – 2 Apr
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
13–20 Mar
Cottage in Coral Gables
5.0 out of 5 average rating, 37 reviewsNew Modern Near Airport - Cozy Very Clean
11–18 Mar
Cottage in Miami
4.92 out of 5 average rating, 12 reviewsCozy cottage garden & parking
16–23 Jul
Cottage in Miami
4.91 out of 5 average rating, 70 reviewsCottage-Private Gated Estate w/heated Pool Near UM
13–20 Oct
Cottage in Everglades City
4.85 out of 5 average rating, 66 reviewsPerfect Florida Everglades Cottage
5–12 Dec
Cottage in Hollywood
5.0 out of 5 average rating, 23 reviewsBeautiful 3 bedroom cottage with private rooftop
15–22 Jun
Private cottage rentals
Cottage in Key Largo
4.98 out of 5 average rating, 51 reviewsOceanfront Paradise with Amazing View!
9–16 Apr
Cottage in Key Largo
4.9 out of 5 average rating, 49 reviewsTHE PARADISE
17–24 Oct
Cottage in Islamorada
4.97 out of 5 average rating, 66 reviewsKey Lime Cottage 2br 1ba w/pool
11–18 Jul
Cottage in Islamorada
4.95 out of 5 average rating, 40 reviewsIslamorada bungalow 2 bed & pool
12–19 Nov
Cottage in Marathon
4.95 out of 5 average rating, 22 reviewsCatch n' Relax Canalfront Cottage in Marathon
29 Oct – 5 Nov
Cottage in Naples
4.96 out of 5 average rating, 26 reviewsCozy Cottage Near Beach, Restaurants and Fun
3–10 Oct
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
26 Aug – 2 Sep
Cottage in Miami
4.62 out of 5 average rating, 303 reviewsHistoric Casa Havana - Studio Cottage
3–10 Jun
Destinations to explore
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- West Palm Beach Holiday rentals
- Varadero Holiday rentals
- Havana Holiday rentals
- Nassau Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Cottage rentals Miami
- Cottage rentals Florida
- Cottage rentals Fort Lauderdale
- Campsite rentals Florida Keys
- Rentals with an accessible height toilet Florida Keys
- Resort rentals Florida Keys
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- Beach condo rentals Florida Keys
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- Rentals with a kayak Florida Keys
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- Rentals with beach access Florida Keys
- Bungalow rentals Florida Keys
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- Rentals with lake access Florida Keys
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- Monthly Rentals Florida Keys
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- Rentals with a hot tub Florida Keys
- RV rentals Florida Keys
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- Townhouse rentals Florida Keys
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- Rentals with pools Florida Keys
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- Serviced apartment rentals Florida Keys
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- Tiny house rentals Florida Keys
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