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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Apartment in Islamorada
Luxury condo with boat slip overlooking the bay
3 bedrooms, 3 beds, 2.5 private bathrooms
3–10 Oct
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5.0 out of 5 average rating, 36 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
La Siesta Resort & Villas, Oceanfront Studio Suite.
1 bedroom, 2 king beds, 1 bathroom
7–12 Nov
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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
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
1–7 Oct
5.0 out of 5 average rating, 17 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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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
Flakey's
2 bedrooms, 3 beds, 1 bathroom
3–10 Oct
4.97 out of 5 average rating, 220 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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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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Flat in Tavernier
Florida Keys Escape | Beach, Pool & Marina
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
New place to stay
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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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Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
6–13 Nov
5.0 out of 5 average rating, 56 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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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
16–21 Oct
4.97 out of 5 average rating, 35 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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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
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