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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 private bathrooms
2–7 Oct
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4.97 out of 5 average rating, 35 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
1–8 Oct
5.0 out of 5 average rating, 3 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
1–6 Oct
4.96 out of 5 average rating, 79 reviews
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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 394 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
12–17 Oct
5.0 out of 5 average rating, 9 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
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Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 24 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, 103 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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Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
14–21 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
18–23 Oct
4.88 out of 5 average rating, 8 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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Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
2–7 Oct
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
7–14 Oct
4.92 out of 5 average rating, 24 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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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
10–17 Oct
New place to stay
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Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
4–11 Oct
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Villa in Islamorada
Isla Key Lime: FREE Boat Dockage Sept-Oct Only!
3 bedrooms, 3 beds, 3.5 bathrooms
7–14 Oct
5.0 out of 5 average rating, 14 reviews