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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
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Jul
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
25 Jul – 1 Aug
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 215 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
2–9 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
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
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
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
New place to stay, 5 bedrooms, 5 beds, 4.5 bathrooms
31 Jul – 7 Aug
Guest favourite
Home in Key Largo
Private Beach 6BR/6.5BA Estate
5.0 out of 5 average rating, 10 reviews, 6 bedrooms, 6 beds, 6.5 bathrooms
29 Nov – 6 Dec
Guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
4.86 out of 5 average rating, 265 reviews, 2 bedrooms, 2 beds, 2 bathrooms
7–12 Aug
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
4.91 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Home in Islamorada
Pristine Islamorada Pool Home with Ocean View and
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
20–25 Jul
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