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Search results; Over 1,000 places

Superhost
Houseboat in Marathon
Houseboat Getaway In Marathon
On a private beachKayak, Boat berth,
12–17 Jun
4.84 out of 5 average rating, 62 reviews
Boat in Marathon
Paradise awaits on this cozy houseboat!
1 king bed
8–13 May
4.77 out of 5 average rating, 162 reviews
Home in Big Pine Key
Boater's Paradise with Dock
2 beds
19–24 Feb
5.0 out of 5 average rating, 4 reviews
Guest favourite
Room in Marathon
Stay with CharlesHosting for 7 years,
Island Yacht Adventures
19–24 May
4.99 out of 5 average rating, 397 reviews
Home in Big Pine Key
Nature's Paradise-Ingrd Pool-Great Monthly Rental$
4 beds
15–22 May
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 queen bed
9–14 May
5.0 out of 5 average rating, 7 reviews
Guest favourite
Campervan/Motorhome in Big Pine Key
You’re on island time at The Island Girl
4 beds
19–24 May
4.89 out of 5 average rating, 44 reviews
Superhost
Cabin in Marathon
New Cabins at Bonefish Bay
3 beds
18–23 May
4.9 out of 5 average rating, 21 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
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
Guest suite in Marathon
Casa Mariposa: Easy walk to Sombrero Beach
1 king bed
3–10 May
4.98 out of 5 average rating, 184 reviews
Superhost
Home in Big Pine Key
Home in Big Pine Key
2 beds
23–28 Apr
5.0 out of 5 average rating, 12 reviews
Guest favourite
Guest suite in Marathon
Casa Mariposa: Sombrero Beach Neighborhood
2 single beds
27 Apr – 4 May
4.98 out of 5 average rating, 142 reviews
Guest favourite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
4 beds
26–31 May
4.91 out of 5 average rating, 145 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
Superhost
Home in Upper Sugarloaf Key
Bungalows at Sugarloaf Beach - The Lighthouse
1 sofa bed
19–24 May
4.87 out of 5 average rating, 45 reviews
Guest favourite
Villa in Duck Key
★Beautiful Gated Oasis★with private pool and patio
5 beds
29 Apr – 4 May
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
WaterfrontSea and bay views,
17–22 Aug
4.97 out of 5 average rating, 61 reviews