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Search results; Over 1,000 places

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Boat in Marathon
Paradise awaits on this cozy houseboat!
1 king bed
8–13 May
4.77 out of 5 average rating, 162 reviews
Guest favourite
Room in Marathon
Stay with CharlesHosting for 7 years,
Island Yacht Adventures
19–24 MayIndividual Host,
4.99 out of 5 average rating, 397 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit 1 Queen Bed, Full Kitchen
Professional Host
21–26 Apr
4.86 out of 5 average rating, 42 reviews
Farm stay in Homestead
Everglades Organic Farm Oasis
4 beds
20–25 Apr
4.76 out of 5 average rating, 25 reviews
Guest favourite
Home in Ramrod Key
Canalfront 3BD/2BA|FLKeys|POOL|DOCK
6 beds
6–11 Mar
5.0 out of 5 average rating, 6 reviews
Home in Marathon
Sunset Cottage on Morton Street
Professional Host
20–27 Apr
New place to stay
Home in Big Pine Key
Boater's Paradise with Dock
Professional Host
19–24 Feb
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest suite in Big Pine Key
Old Island Life
1 queen bed
28 Apr – 3 May
4.87 out of 5 average rating, 471 reviews
Guest favourite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
Professional Host
1–8 Oct
4.94 out of 5 average rating, 17 reviews
Guest favourite
Guest suite in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
Individual Host
3–10 May
4.98 out of 5 average rating, 184 reviews
Superhost
Cabin in Marathon
New Cabins at Bonefish Bay
3 beds
18–23 May
4.9 out of 5 average rating, 21 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
2 beds
18–23 May
4.89 out of 5 average rating, 145 reviews
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
Professional Host
16–21 May
4.94 out of 5 average rating, 16 reviews
Home in Key West
Waterfront Key West House w/Dock
6 beds
8–14 May
5.0 out of 5 average rating, 4 reviews
Superhost
Houseboat in Key West
The Crystalmarine Suite – Rustic Luxury on the Sea
1 bed
26–31 May
4.92 out of 5 average rating, 39 reviews
Guest favourite
Farm stay in Homestead
Modern Farm House on a 12 acre Dragon Fruit Farm
Individual Host
27 Apr – 2 May
4.96 out of 5 average rating, 125 reviews
Guest favourite
Home in Cudjoe Key
Paradise at Cudjoe Bay
2 king beds
28 May – 2 Jun
4.91 out of 5 average rating, 138 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
28 Apr – 3 May
4.86 out of 5 average rating, 42 reviews