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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 391 reviews
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed, 1 bathroom
7–12 Sept
4.86 out of 5 average rating, 7 reviews
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.8 out of 5 average rating, 51 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
18–25 Sept
5.0 out of 5 average rating, 17 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
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
8–13 Sept
4.8 out of 5 average rating, 5 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, 219 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
8–15 Sept
New place to stay
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
23–28 Nov
4.96 out of 5 average rating, 151 reviews
Featured hotel
Room in Key Largo
Cottage 3
1 king bed, 1 bathroom
13–18 Sept
Top guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 48 reviews
Featured hotel
Room in Islamorada
One bedroom suite garden view two queen
3 queen beds, 1 bathroom
3–8 Sept