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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 private bathroom
18–23 Sept
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4.96 out of 5 average rating, 79 reviews
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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
18–25 Sept
5.0 out of 5 average rating, 14 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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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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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 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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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 394 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
18–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
18–24 Sept
5.0 out of 5 average rating, 17 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, 7 reviews
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Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
29 Oct – 3 Nov
4.98 out of 5 average rating, 62 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
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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
4.87 out of 5 average rating, 47 reviews
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Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 142 reviews
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Guest favourite
Flat in Tavernier
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 295 reviews
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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
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
Boat in Islamorada
HOUSEBOAT 2BD, 1 BATH PRIVATE KEYS COTTAGE MULLET
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.83 out of 5 average rating, 221 reviews
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Top guest favourite
Home in Key Largo
Ocean view, seaside paradise with golf cart.
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 77 reviews