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Search results; Over 1,000 homes in Islamorada

Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds, 2.5 private bathrooms
3–10 Oct
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5.0 out of 5 average rating, 5 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
1–8 Sept
New place to stay
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
1–8 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 391 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 bathrooms
1–8 Sept
4.92 out of 5 average rating, 24 reviews
Superhost
Home in Marathon
Mar de Cielo - Waterfront - Heated Pool - Dock
4 bedrooms, 9 beds, 3 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
1–7 Sept
4.97 out of 5 average rating, 34 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
1–6 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 89 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
1–8 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.8 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.97 out of 5 average rating, 97 reviews