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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
23–28 Sept
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4.95 out of 5 average rating, 105 reviews
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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 393 reviews
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 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
17–22 Sept
4.96 out of 5 average rating, 79 reviews
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Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
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Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
12–17 Oct
4.83 out of 5 average rating, 6 reviews
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Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
17–24 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
17–24 Sept
5.0 out of 5 average rating, 14 reviews
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Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
4.77 out of 5 average rating, 53 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
6–11 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
17–23 Sept
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
24–31 Oct
5.0 out of 5 average rating, 13 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
4.87 out of 5 average rating, 47 reviews
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Serviced apartment in Islamorada
Proximity Ats its Best! 2 Units, Pool + Breakfast!
2 bedrooms, 4 double beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
2–7 Oct
4.94 out of 5 average rating, 17 reviews
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Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.84 out of 5 average rating, 123 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
18–25 Sept
5.0 out of 5 average rating, 15 reviews