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 cottage rentals in Florida Keys
Cottage rentals with a hot tub
Cottage in Cudjoe Key
4.91 out of 5 average rating, 79 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
25 Sept – 2 Oct
Cottage in Key West
4.82 out of 5 average rating, 22 reviewsDarling of Duval @ Old Town - Adorable Cottage
31 Aug – 7 Sept
Cottage in Fort Lauderdale
5.0 out of 5 average rating, 87 reviewsPrivate Couple’s cottage. Hotub. Beach. Miami
7–14 Dec
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
21–28 Sept
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
15–22 Nov
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
1–8 Sept
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
25 Aug – 1 Sept
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
22–29 Nov
Pet-friendly cottage rentals
Cottage in Naples
4.94 out of 5 average rating, 140 reviewsMango Tree Cottage close to Beach
4–11 Mar
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
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 Naples
5.0 out of 5 average rating, 12 reviewsCozyCove
25 Jun – 2 Jul
Cottage in Coral Gables
5.0 out of 5 average rating, 37 reviewsNew Modern Near Airport - Cozy Very Clean
24–31 Oct
Cottage in Miami
4.92 out of 5 average rating, 12 reviewsCozy cottage garden & parking
8–15 Jul
Cottage in Miami
4.91 out of 5 average rating, 70 reviewsCottage-Private Gated Estate w/heated Pool Near UM
1–8 Jul
Private cottage rentals
Cottage in Miami
4.87 out of 5 average rating, 250 reviewsRuben’s Place
25 Jan – 1 Feb
Cottage in Fort Lauderdale
4.83 out of 5 average rating, 456 reviewsHistoric Renovated Cottage w/ Private Heated Pool!
28 Aug – 4 Sept
Cottage in Hollywood
5.0 out of 5 average rating, 101 reviewsCozy beach cottage steps away from Hollywood Beach
8–15 Jan
Cottage in Key Largo
4.98 out of 5 average rating, 51 reviewsOceanfront Paradise with Amazing View!
12–19 Jan
Cottage in Key Largo
4.9 out of 5 average rating, 48 reviewsTHE PARADISE
7–14 Sept
Cottage in Islamorada
4.95 out of 5 average rating, 40 reviewsIslamorada bungalow 2 beds & pool
17–24 Oct
Cottage in Islamorada
4.97 out of 5 average rating, 66 reviewsKey Lime Cottage 2br 1ba w/pool
27 Oct – 3 Nov
Cottage in Marathon
4.95 out of 5 average rating, 22 reviewsCatch n' Relax Canalfront Cottage in Marathon
16–23 Oct
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
- Rentals with a patio Florida Keys
- Beach house rentals Florida Keys
- Private suite rentals Florida Keys
- Tiny house rentals Florida Keys
- Hotel rentals Florida Keys
- Beach apartment rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Rentals with a kayak Florida Keys
- Mansion rentals Florida Keys
- Rentals with a cinema Florida Keys
- Wheelchair-accessible rentals Florida Keys
- Motorhome rentals Florida Keys
- Rentals with an accessible-height bed Florida Keys
- Family-friendly rentals Florida Keys
- Townhouse rentals Florida Keys
- Monthly Rentals Florida Keys
- Campsite rentals Florida Keys
- Rentals with pools Florida Keys
- Bungalow rentals Florida Keys
- Houseboat rentals Florida Keys
- Smoking-friendly rentals Florida Keys
- House rentals Florida Keys
- Boat rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Resort rentals Florida Keys
- Apartment rentals Florida Keys
- Rentals with a firepit Florida Keys
- Family-friendly rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Rentals with a fireplace Florida Keys
- Waterfront rentals Florida Keys
- Boutique hotel rentals Florida Keys
- Guest house rentals Florida Keys
- Beachfront rentals Florida Keys
- Rentals with an accessible-height toilet Florida Keys
- Flat rentals Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with a sauna Florida Keys
- Bed and breakfasts Florida Keys
- Villa rentals Florida Keys
- Rentals with lake access Florida Keys
- Fitness-friendly rentals Florida Keys
- Rentals with breakfast Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with beach access Florida Keys
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