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Search results; Over 1,000 homes

Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 private bathroom
1–6 Aug
,
4.88 out of 5 average rating, 182 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.95 out of 5 average rating, 114 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.96 out of 5 average rating, 52 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
13–20 Jul
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
New place to stay
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 6 Sept
New place to stay
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 30 reviews
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
4 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 25 reviews
Hotel room in Little Torch Key
Tropical Escape w/ Kitchen, Breakfast & Pool!
3 bedrooms, 1 bathroom
21–26 Jul
Top guest favourite
Holiday home in Key Colony Beach
Waterfront 4BR | Dual Living | Hot Tub | Dock
4 bedrooms, 4 beds, 3 bathrooms
22–27 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
5.0 out of 5 average rating, 85 reviews