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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
29 Jul – 3 Aug
,
4.93 out of 5 average rating, 384 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
13–18 Jul
New place to stay
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
1–8 Jul
New place to stay
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.86 out of 5 average rating, 35 reviews
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds, 4.5 bathrooms
6–13 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
10–17 Jul
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Islamorada
Brand-New 4BR Island Home in Central Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
1–8 Jul
New place to stay
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
25 Jul – 1 Aug
4.97 out of 5 average rating, 213 reviews
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds, 3 bathrooms
1–8 Jul
4.89 out of 5 average rating, 9 reviews
Superhost
Home in Islamorada
Pineapple Beach
5 bedrooms, 13 beds, 4.5 bathrooms
4–11 Jul
Guest favourite
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds, 2.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
7–12 Aug
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
4.97 out of 5 average rating, 144 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
4–11 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Islamorada
FL Keys Ocean Front Escape
2 bedrooms, 2 beds, 3 bathrooms
1–8 Jul
5.0 out of 5 average rating, 9 reviews
Featured hotel
Hotel in Islamorada
Matacumbe courtyard view king accessible Lanai
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Home in Marathon
Water Views | Private Pool Oasis + Gazebo + Kayaks
4 bedrooms, 7 beds, 4.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 13 reviews
Home in Islamorada
Oceanside Islamorada 2/2.5 Home-Pool, Beach, Dock
2 bedrooms, 5 beds, 2.5 bathrooms
4–11 Jul