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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
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 50 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 68 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Home in Key Largo
The charm
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 16 reviews
Featured hotel
Room in Tavernier
One bedroom ocean view suite - provident signature
1 bathroom
17–22 Aug
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
4.97 out of 5 average rating, 217 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.9 out of 5 average rating, 48 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
4.87 out of 5 average rating, 46 reviews
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 274 reviews
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds, 2.5 bathrooms
8–15 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug
4.95 out of 5 average rating, 21 reviews