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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
,
4.93 out of 5 average rating, 386 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
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 bathrooms
10–17 Jul
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 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
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
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
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
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
Featured hotel
Hotel in Islamorada
Matacumbe courtyard view room two queens Lanai
1 bedroom, 1 bathroom
4–9 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 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 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
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
New place to stay, 5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 6 Sept
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 214 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 3 bathrooms
18–25 Jul
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
New place to stay, 4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
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
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