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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
9–14 Jul
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4.93 out of 5 average rating, 385 reviews
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
4.86 out of 5 average rating, 35 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Home in Islamorada
Margaritaville
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 214 reviews, 2 bedrooms, 3 beds, 1 bathroom
25 Jul – 1 Aug
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
7–14 Jul
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 3 bathrooms
4–11 Sept
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
5–12 Aug
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 31 reviews, 3 bedrooms, 3 bathrooms
9–15 Aug
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
Guest favourite
Apartment in Tavernier
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
4.91 out of 5 average rating, 160 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 3 bathrooms
18–25 Jul
Guest favourite
Townhouse in Key Largo
Sunrise Retreat: Ocean & Pool Views, Gym, PB Court
4.89 out of 5 average rating, 65 reviews, 3 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
New place to stay, 2 bedrooms, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Flat in Tavernier
Marina & Ocean Front Suite 5202
4.97 out of 5 average rating, 31 reviews, 2 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
23–30 Aug
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
4.94 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
16–23 Jul