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Search results; Over 1,000 homes in Islamorada

Serviced apartment in Islamorada
Deluxe Villa, Windley Key Fossil Reef + Breakfast!
1 bedroom, 1 private bathroom
14–19 Sept
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Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
26 Sept – 3 Oct
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
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
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds
19–26 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
14–20 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
20–26 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
14–21 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
14–19 Sept
4.96 out of 5 average rating, 79 reviews
Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds
14–19 Sept
5.0 out of 5 average rating, 7 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
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds
30 Oct – 4 Nov
4.87 out of 5 average rating, 47 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
12–17 Oct
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
24–29 Sept
4.96 out of 5 average rating, 142 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
14–19 Sept
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
14–21 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Apartment in Islamorada
5-Star Sandy Beach Sunsets & Pool in Best Location
4 bedrooms, 7 beds
14–19 Sept
5.0 out of 5 average rating, 19 reviews