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Search results; Over 1,000 homes in Islamorada

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Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 private bathrooms
2–7 Oct
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4.97 out of 5 average rating, 35 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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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
10–17 Oct
New place to stay
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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
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 9 reviews
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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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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 Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 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
1–7 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
5.0 out of 5 average rating, 81 reviews
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Guest favourite
Flat in Tavernier
Atlantic Serenity 2407 Ocean Pointe 2 BA 2 BR
2 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 11 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
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
7–14 Oct
4.92 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
4–11 Oct
5.0 out of 5 average rating, 27 reviews
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Superhost
Townhouse in Marathon
Florida Keys Group Getaway at Salt Kissed
7 bedrooms, 9 beds, 6 bathrooms
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
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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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Top guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
15–22 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 6 reviews