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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
4 bedrooms, 4 king beds, 4 bathrooms
3–9 Aug
New place to stay
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds, 3 bathrooms
7–12 May
4.96 out of 5 average rating, 69 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
7 bedrooms, 7 king beds, 7 bathrooms
17–22 Aug
New place to stay
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 34 reviews
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
3–10 Aug
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
7–14 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
4.87 out of 5 average rating, 46 reviews
Top guest favourite
Home in Key Largo
The charm
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 15 reviews