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Search results; Over 1,000 homes in Islamorada

Guest favourite
Apartment in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 bedrooms, 2 beds, 2.5 private bathrooms
21–28 Aug
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4.94 out of 5 average rating, 33 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
20–25 Aug
New place to stay
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
15–21 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
Top guest favourite
Home in Islamorada
4-Bedroom Coastal Retreat *Special Fall Rates*
4 bedrooms, 4.5 bathrooms
17–24 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
4.86 out of 5 average rating, 36 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
20–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Villa in Islamorada
Isla Key Lime: FREE Boat Dockage Sept-Oct Only!
3 bedrooms, 3 beds, 3.5 bathrooms
15–22 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.9 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 110 reviews
Guest favourite
Home in Marathon
Oceanfront Sunsets | Kayaks-Pool-Dock-Putt Green
4 bedrooms, 4 beds, 3 bathrooms
26 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Marathon
New oceanfront 5BR home w/pool, slip, and beach
5 bedrooms, 8 beds, 4 bathrooms
16–23 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug
4.95 out of 5 average rating, 22 reviews