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Search results; Over 1,000 homes in Islamorada

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Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.8 out of 5 average rating, 91 reviews
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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Sept
4.93 out of 5 average rating, 394 reviews
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
14–19 Oct
4.83 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
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
28 Sept – 3 Oct
5.0 out of 5 average rating, 8 reviews
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Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
20–25 Sept
4.77 out of 5 average rating, 53 reviews
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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
18–23 Sept
4.96 out of 5 average rating, 79 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
25 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds
18–23 Sept
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 101 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
18–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
29 Sept – 4 Oct
4.94 out of 5 average rating, 160 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds
18–24 Sept
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Apartment in Tavernier
Condo in Tavernier
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 55 reviews
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Superhost
Flat in Tavernier
When Paradise is Key: Tropical Oceanfront Condo
2 bedrooms, 5 beds
25–30 Oct
4.88 out of 5 average rating, 102 reviews
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Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds
30 Oct – 6 Nov
4.92 out of 5 average rating, 12 reviews
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Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds
11–16 Oct
4.84 out of 5 average rating, 123 reviews
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Top guest favourite
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds
18–23 Sept
4.92 out of 5 average rating, 401 reviews