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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 private bathrooms
10–17 Oct
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5.0 out of 5 average rating, 15 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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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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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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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 394 reviews
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Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 160 reviews
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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
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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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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Guest favourite
Cottage in Key Largo
Cottage By The Sea
2 bedrooms, 3 beds, 1.5 bathrooms
21–26 Oct
4.9 out of 5 average rating, 422 reviews
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Guest favourite
Flat in Tavernier
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 249 reviews
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Guest favourite
Flat in Tavernier
Keys Tree House
1 bedroom, 1 bed, 1 bathroom
22–29 Nov
4.89 out of 5 average rating, 9 reviews
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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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Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 103 reviews
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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 79 reviews
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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
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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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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
2–7 Oct
4.97 out of 5 average rating, 35 reviews