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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
29 Jul – 3 Aug
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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
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 213 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
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
1–8 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
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
17–22 Aug
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
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
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Guest favourite
Flat in Tavernier
Welcome to the Pelican Lodge !
4.91 out of 5 average rating, 33 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
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
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
4.97 out of 5 average rating, 62 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Flat in Tavernier
Panoramic Ocean Views, Ocean Pointe Condo
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 2 bathrooms
6–11 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
Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft
4.99 out of 5 average rating, 96 reviews, 2 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
Guest favourite
Apartment in Key Largo
Gorgeous lagoon-front 2BR Townhouse with 2 pools
4.91 out of 5 average rating, 161 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top 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