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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
9–14 Aug
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4.93 out of 5 average rating, 387 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
3–9 Aug
New place to stay
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds
10–15 Aug
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
9–15 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
15–22 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 216 reviews
Featured hotel
Room in Key Largo
Cottage 6
2 queen beds
11–16 Aug
New place to stay
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
14–19 Aug
New place to stay
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
7–14 Aug
5.0 out of 5 average rating, 9 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed
2–7 Aug
4.91 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds
1–6 Aug
4.97 out of 5 average rating, 103 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds
2–9 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds
13–20 Aug
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds
7–14 Aug
4.96 out of 5 average rating, 26 reviews
Luxe
Home in Islamorada
Private Beach / Pickleball Court and Tiki Bar
6 bedrooms, 8 king beds
16–23 Aug
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds
8–15 Aug
Home in Islamorada
Charming Beach House directly ON the beach
4 bedrooms, 6 beds
17–24 Aug
5.0 out of 5 average rating, 6 reviews