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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.93 out of 5 average rating, 394 reviews
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Featured hotel
Hotel in Islamorada
La Siesta Resort & Villas, Studio suite garden vi.
1 bedroom, 3 queen beds, 1 bathroom
31 Oct – 5 Nov
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Featured hotel
Hotel in Islamorada
Amara Cay Resort, One bedroom standard view suite.
1 bedroom, 3 queen beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 15 reviews
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Featured hotel
Hotel in Islamorada
La Siesta Resort & Villas, Studio suite ocean fro.
1 bedroom, 2 king beds, 1 bathroom
7–12 Nov
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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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Featured hotel
Hotel in Key Largo
Sunset Cove Beach Resort, Cottage 3
1 bedroom, 1 king bed, 1 bathroom
2–7 Oct
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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
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
29 Oct – 3 Nov
4.84 out of 5 average rating, 123 reviews
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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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Guest favourite
Home in Islamorada
Waterfront / Ocean Access Canal / Kamp Key
3 bedrooms, 3 king beds, 3 bathrooms
7–12 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Islamorada
4-Bedroom Heart of Islamorada *Last Minute Deals*
4 bedrooms, 5 beds, 4.5 bathrooms
6–13 Oct
5.0 out of 5 average rating, 12 reviews
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Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
10–17 Oct
New place to stay
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Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Oct
5.0 out of 5 average rating, 3 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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Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 106 reviews
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Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 bathrooms
1–8 Oct
4.92 out of 5 average rating, 24 reviews
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Superhost
Apartment in Islamorada
A Slice of Islamorada Paradise with Ocean Views
2 beds, 1 bathroom
3–8 Oct
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Luxe
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
6–11 Oct