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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
1–6 Aug
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4.93 out of 5 average rating, 385 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
Islamorada Bungalow # 5
4.86 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
New place to stay, 5 bedrooms, 5 beds, 4.5 bathrooms
12–19 Jul
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 214 reviews, 2 bedrooms, 3 beds, 1 bathroom
25 Jul – 1 Aug
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
4–11 Sept
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
8–15 Jul
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
12–17 Jul
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
Featured hotel
Hotel in Islamorada
Alligator reef oceanfront room king
1 bedroom, 1 bathroom
9–14 Aug
Luxe
Villa in Islamorada
4 Bedroom Oceanfront Accessible Villa – Capacity 8
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
11–18 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
10–17 Jul
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
23–30 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
Guest favourite
Home in Key Largo
The charm
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
8–15 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