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Search results; Over 1,000 homes in Islamorada

Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 private bathroom
15–20 Sept
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4.96 out of 5 average rating, 79 reviews
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 3 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Rooms in Key Largo
The dolphin waterfront suite
2 bedrooms, 1 bathroom
20–25 Sept
Featured hotel
Room in Key Largo
Cottage 1
2 queen beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
15–20 Sept
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed, 2 bathrooms
29 Sept – 4 Oct
4.94 out of 5 average rating, 160 reviews
Featured hotel
Hotel in Islamorada
Studio suite ocean front one king
1 bedroom, 2 king beds, 1 bathroom
7–12 Nov
Guest favourite
Flat in Tavernier
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 247 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
Featured hotel
Hotel in Marathon
Superior two bedroom suite
2 bedrooms, 1 bathroom
20–25 Sept
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 142 reviews
Guest favourite
Boat in Islamorada
HOUSEBOAT 2BD, 1 BATH PRIVATE KEYS COTTAGE MULLET
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.83 out of 5 average rating, 221 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 16 reviews
Featured hotel
Hotel in Islamorada
One bedroom suite garden view two queen
1 bedroom, 3 queen beds, 1 bathroom
31 Oct – 5 Nov
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 23 reviews