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Search results; Over 1,000 homes in Islamorada

Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 private bathrooms
2–9 Sept
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4.92 out of 5 average rating, 24 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
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
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
2–7 Sept
4.96 out of 5 average rating, 141 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
8–13 Sept
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds
5–10 Oct
4.98 out of 5 average rating, 61 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
6–11 Sept
4.8 out of 5 average rating, 51 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
8–15 Sept
New place to stay
Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
13–18 Sept
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
21–26 Sept
4.94 out of 5 average rating, 158 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds
14–19 Sept
4.87 out of 5 average rating, 181 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews