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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Apartment in Islamorada
Luxury condo with boat slip overlooking the bay
3 bedrooms, 3 beds, 2.5 private bathrooms
15–22 Aug
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5.0 out of 5 average rating, 36 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
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
13–20 Aug
New place to stay
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 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
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 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, 388 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
7–14 Aug
5.0 out of 5 average rating, 12 reviews
Home in Islamorada
Heart of Morada - Dock & Pool
3 bedrooms, 3 king beds, 3.5 bathrooms
7–14 Aug
New place to stay
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
4.83 out of 5 average rating, 117 reviews
Featured hotel
Room in Key Largo
Waterfront suite 9
1 bathroom
16–21 Aug
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 34 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.96 out of 5 average rating, 149 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
8–15 Aug
4.96 out of 5 average rating, 27 reviews