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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
3–10 Aug
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
New place to stay, 8 bathrooms
9–16 Aug
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 Islamorada
Flakey's
4.97 out of 5 average rating, 215 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 53 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 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
7–14 Aug
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 1 bed, 3 bathrooms
9–14 Aug
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
2–9 Aug
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
1–8 Aug
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
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
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
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
2 queen beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Villa in Islamorada
Islamorada | Maison Residences
4.92 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 6 bathrooms
1–8 Aug
Luxe
Home in Islamorada
Private Beach / Pickleball Court and Tiki Bar
6 bedrooms, 8 beds, 4 bathrooms
16–23 Aug
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept