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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
20–25 Sept
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4.93 out of 5 average rating, 394 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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Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 8 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
19–24 Sept
4.96 out of 5 average rating, 79 reviews
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
14–19 Oct
4.83 out of 5 average rating, 6 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
3–10 Oct
New place to stay
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Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
11–18 Dec
5.0 out of 5 average rating, 56 reviews
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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
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 24 reviews
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Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds, 2 bathrooms
19–24 Sept
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
19–25 Sept
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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Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.77 out of 5 average rating, 53 reviews
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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 14 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
4.9 out of 5 average rating, 20 reviews
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Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 101 reviews
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Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
20–27 Sept
4.96 out of 5 average rating, 27 reviews
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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 35 reviews