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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 private bathrooms
9–16 Sept
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5.0 out of 5 average rating, 23 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 1
2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
9–15 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 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
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
10–15 Sept
4.93 out of 5 average rating, 393 reviews
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
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–14 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
9–16 Sept
New place to stay
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
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
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
15–20 Oct
4.98 out of 5 average rating, 61 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
10–15 Sept
4.8 out of 5 average rating, 5 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
Guest favourite
Villa in Key Largo
Twilight #32 Key Largo 4BR Villa | Pool,
4 bedrooms, 4 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.8 out of 5 average rating, 55 reviews