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Search results; Over 1,000 homes in Islamorada

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
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 387 reviews
Featured hotel
Room in Islamorada
Studio suite garden view king
1 king bed, 1 bathroom
26–31 Aug
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
Guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
11–18 Aug
4.89 out of 5 average rating, 27 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
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
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
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 Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
4.97 out of 5 average rating, 217 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
Guest favourite
Apartment in Tavernier
Coastal Comfort in Tavernier - Pool + Beach Access
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.83 out of 5 average rating, 121 reviews
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Apartment in Tavernier
Swaying Palms Spacious Suite [Ocean Pointe 3201]
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 71 reviews
Superhost
Apartment in Islamorada
A Slice of Islamorada Paradise with Ocean Views
2 beds, 1 bathroom
10–15 Aug
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 104 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
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