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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 private bathroom
8–15 Aug
,
4.97 out of 5 average rating, 215 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
4.93 out of 5 average rating, 387 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
4.96 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
4.97 out of 5 average rating, 65 reviews, 1 bedroom, 1 bed, 1 bathroom
30 May – 4 Jun
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
5.0 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
2 queen beds, 1 bathroom
16–21 Aug
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Apartment in Tavernier
Friends' Getaway 1BR w/ Ocean View, Pool & Beach
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Apartment in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
4.91 out of 5 average rating, 335 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Jul
Featured hotel
Room in Tavernier
Standard one bedroom ocean view suite
4.8 out of 5 average rating, 5 reviews, 1 bathroom
8–13 Aug
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 bathrooms
9–15 Aug
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 53 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
Featured hotel
Room in Islamorada
Matacumbe courtyard view king accessible Lanai
1 king bed, 1 bathroom
8–13 Aug
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
4.95 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug
Top guest favourite
Home in Key Largo
The charm
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug