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Search results; Over 1,000 homes in Islamorada

Descriptions are based on details hosts provide
Guest favourite
Apartment in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 bedrooms, 2 beds, 2.5 private bathrooms
20–27 Aug
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4.94 out of 5 average rating, 32 reviews
Superhost
Villa in Islamorada
Private beach, heated pool, and a dock
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Jul
Top guest favourite
Home in Marathon
Oceanfront with a pool, hot tub, and dock
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Guest favourite
Home in Key Largo
Lakefront pool house with a jacuzzi
4.96 out of 5 average rating, 68 reviews, 3 bedrooms, 6 beds, 3 bathrooms
7–12 May
Top guest favourite
Home in Islamorada
Waterfront estate with pool, dock, and tiki
5.0 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Villa in Key Largo
Waterfront Luxe Pool, Hot Tub, Theater, Games&more
5 bedrooms, 9 beds, 5 bathrooms
16–21 Aug
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 1 bathroom
7–12 Aug
Luxe
Villa in Islamorada
Three-story oceanfront villa with elevator access
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 5 beds, 4 bathrooms
2–7 Aug
Houseboat in Buttonwood Sound
Off-grid floating bungalow on Buttonwood Sound
4.91 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
25 Jul – 1 Aug
Guest favourite
Home in Marathon
Pool, hot tub, and a private dock
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
10–17 Aug
Superhost
Home in Islamorada
Private beach, infinity pool, and dock
New place to stay, 4 bedrooms, 4 beds, 4.5 bathrooms
15–20 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
24–31 Aug
Top guest favourite
Home in Islamorada
Above a brewery, walk to everything
4.97 out of 5 average rating, 215 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Home in Marathon
Bayfront with a pool, dock, and kayaks
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 5 Sept
Guest favourite
Villa in Islamorada
Oceanfront with a private beach and pool
4.92 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 6 bathrooms
20–27 Jul
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
4.89 out of 5 average rating, 35 reviews, 7 bedrooms, 8 beds, 7.5 bathrooms
8–15 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
Villa in Islamorada
Bayside dock and pool, walkable to restaurants
4.94 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug