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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Home in Islamorada
Oceanfront community 114 Anglers Reef Islamorada
2 bedrooms, 4 beds, 2.5 private bathrooms
19–26 Sept
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4.86 out of 5 average rating, 63 reviews
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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
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, 220 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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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
14–19 Oct
4.86 out of 5 average rating, 7 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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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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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
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, 102 reviews
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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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Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds, 3 bathrooms
30 Oct – 6 Nov
4.92 out of 5 average rating, 12 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
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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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
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Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.97 out of 5 average rating, 99 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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Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
4.88 out of 5 average rating, 48 reviews
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Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews