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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
19–24 Sept
,
4.93 out of 5 average rating, 393 reviews
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Featured hotel
Hotel in Key Largo
Cottage 1
1 bedroom, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
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Featured hotel
Hotel in Key Largo
Cottage 2 queen beds
1 bedroom, 2 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 reviews
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
12–17 Oct
4.83 out of 5 average rating, 6 reviews
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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
4.96 out of 5 average rating, 79 reviews
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Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.77 out of 5 average rating, 52 reviews
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Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed, 2 bathrooms
29 Sept – 4 Oct
4.94 out of 5 average rating, 160 reviews
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Top guest favourite
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds, 1 bathroom
16–21 Sept
4.92 out of 5 average rating, 401 reviews
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Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
24 Apr – 1 May
5.0 out of 5 average rating, 56 reviews
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Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds, 2 bathrooms
22–27 Oct
4.89 out of 5 average rating, 19 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
16–23 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.84 out of 5 average rating, 123 reviews
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Top guest favourite
Home in Islamorada
4-Bedroom Heart of Islamorada *Last Minute Deals*
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 113 reviews
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Guest favourite
Houseboat in Islamorada
Off-Grid Islamorada Houseboat
2 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 9 reviews