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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Oct
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4.98 out of 5 average rating, 61 reviews
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed
13–18 Sept
4.86 out of 5 average rating, 7 reviews
Featured hotel
Room in Key Largo
Cottage 1
2 queen beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds
21–26 Sept
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
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
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
10–17 Sept
5.0 out of 5 average rating, 23 reviews
Featured hotel
Rooms in Marathon
Superior two bedroom suite
2 bedrooms
18–23 Sept
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
10–16 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
10–15 Sept
4.94 out of 5 average rating, 159 reviews
Featured hotel
Room in Islamorada
One bedroom suite garden view two queen
3 queen beds
31 Oct – 5 Nov
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds
10–17 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds
13–18 Sept
4.84 out of 5 average rating, 123 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
10–15 Sept
4.96 out of 5 average rating, 151 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