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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
9–14 Aug
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4.93 out of 5 average rating, 387 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
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
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
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
15–22 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
20–25 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
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
5.0 out of 5 average rating, 112 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
29 Aug – 5 Sept
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
New place to stay, 4 bedrooms, 4 beds, 4.5 bathrooms
18–23 Jul
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
4.96 out of 5 average rating, 68 reviews, 3 bedrooms, 6 beds, 3 bathrooms
7–12 May
Guest favourite
Home in Key Largo
3BR Oceanview Oasis: Pool, Spa & Elevator
4.86 out of 5 average rating, 43 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4.96 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
24–31 Jul
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
5.0 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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
13–20 Aug
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug