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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Houseboat in Islamorada
Perfect escape to the ocean
2 bedrooms, 3 beds, 1 private bathroom
12–17 Oct
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4.79 out of 5 average rating, 68 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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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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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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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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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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Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
1–6 Dec
5.0 out of 5 average rating, 9 reviews
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Superhost
Villa in Islamorada
Isla Acai: FREE Boat Dockage Sep-Oct Only!
3 bedrooms, 3 beds, 3.5 bathrooms
5–12 Oct
4.75 out of 5 average rating, 8 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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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
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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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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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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Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
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Guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.91 out of 5 average rating, 55 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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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
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Cottage in Islamorada
Floating 2 BD, 1 BATH Private Villa Pirates Lair
2 bedrooms, 1 queen bed, 1 bathroom
1–6 Oct
4.79 out of 5 average rating, 43 reviews