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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds, 2.5 private bathrooms
10–17 Oct
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4.98 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
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
12–17 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds
3–10 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
1–6 Oct
4.96 out of 5 average rating, 79 reviews
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Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
11–18 Dec
5.0 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
3–10 Oct
4.97 out of 5 average rating, 220 reviews
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Luxe
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
6–11 Oct
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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
18–23 Oct
4.88 out of 5 average rating, 8 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
1–8 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds
3–8 Oct
4.97 out of 5 average rating, 99 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
1–8 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds
10–17 Oct
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Islamorada
4-Bedroom Coastal Retreat *Special Fall Rates*
4 bedrooms
5–12 Oct
5.0 out of 5 average rating, 11 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
1–6 Oct
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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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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, 102 reviews
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Guest favourite
Hotel in Islamorada
Resort View Single Queen w/ Private Porch
1 bedroom, 1 queen bed
2–7 Oct
4.89 out of 5 average rating, 53 reviews