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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 105 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 1
2 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
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 | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds
12–17 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
9–15 Sept
5.0 out of 5 average rating, 17 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
11–16 Sept
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
9–14 Sept
4.97 out of 5 average rating, 35 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
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
3 queen beds
10–15 Nov
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
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, 159 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
10–15 Sept
4.93 out of 5 average rating, 392 reviews
Guest favourite
Townhouse in Key Largo
Good Vibes Only!!! 2 bedroom/2 bath townhouse
2 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
9–16 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds
11–16 Sept
4.99 out of 5 average rating, 112 reviews