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Search results; Over 1,000 homes in Islamorada

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Featured hotel
Hotel in Islamorada
La Siesta Resort & Villas, Studio suite garden vi.
1 bedroom, 3 queen beds
31 Oct – 5 Nov
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Featured hotel
Hotel in Islamorada
La Siesta Resort & Villas, Oceanfront Studio Suite.
1 bedroom, 2 king beds
7–12 Nov
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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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Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 3 queen beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Tavernier
Keys Tree House
1 bedroom, 1 bed
22–29 Nov
4.89 out of 5 average rating, 9 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds
1–7 Oct
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
6–13 Nov
5.0 out of 5 average rating, 56 reviews
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Featured hotel
Hotel in Key Largo
Sunset Cove Beach Resort, Cottage 3
1 bedroom, 1 king bed
2–7 Oct
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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
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
1–6 Oct
4.94 out of 5 average rating, 160 reviews
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Top guest favourite
Home in Islamorada
4-Bedroom Heart of Islamorada *Last Minute Deals*
4 bedrooms, 5 beds
6–11 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds
1–8 Oct
4.92 out of 5 average rating, 24 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
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds
4–9 Oct
4.92 out of 5 average rating, 401 reviews
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Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds
1–8 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Cottage in Islamorada
2BR Island Cottage | Pool • Grill • Near Robbie’s
2 bedrooms, 3 beds
23–28 Nov
4.96 out of 5 average rating, 152 reviews
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Superhost
Apartment in Islamorada
A Slice of Islamorada Paradise with Ocean Views
2 beds
3–8 Oct
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Featured hotel
Hotel in Key Largo
The Pelican Key Largo Cottages, Cottage queen bed
1 bedroom, 1 queen bed
1–6 Oct
4.89 out of 5 average rating, 9 reviews