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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 private bathrooms
18–25 Sept
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4.92 out of 5 average rating, 24 reviews
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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
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
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
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
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
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
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
18–25 Sept
5.0 out of 5 average rating, 3 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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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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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
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 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, 7 reviews
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Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds
30 Oct – 4 Nov
4.87 out of 5 average rating, 47 reviews
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Top guest favourite
Apartment in Tavernier
Turtle Nest 1 Private beach,Pool, 2bed 2bath
2 bedrooms, 2 beds
22–27 Sept
4.91 out of 5 average rating, 144 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
27 Sept – 2 Oct
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Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
24–29 Sept
4.96 out of 5 average rating, 142 reviews
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Guest favourite
Flat in Tavernier
Atlantic Serenity 2407 Ocean Pointe 2 BA 2 BR
2 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds
20–25 Sept
4.99 out of 5 average rating, 113 reviews