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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
12–17 Jul
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4.98 out of 5 average rating, 60 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
Guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 3 bathrooms
18–25 Jul
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
12–19 Jul
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
4.86 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 3 bathrooms
18–25 Jul
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
11–18 Jul
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
11–18 Jul
Guest favourite
Home in Key Largo
The charm
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 5 Sept
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
Featured hotel
Hotel in Key Largo
The roseatte waterfront suite
New place to stay, 1 bedroom, 1 bathroom
2–7 Aug
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
4.88 out of 5 average rating, 34 reviews, 7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
Featured hotel
Hotel in Islamorada
Ocean front cottage accessible
1 bedroom, 1 bathroom
12–17 Jul
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
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 4 beds, 2 bathrooms
25 Aug – 1 Sept