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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
3–10 Aug
New place to stay
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
9–15 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 215 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
15–22 Sept
5.0 out of 5 average rating, 53 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
9–16 Aug
New place to stay
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds
7–14 Aug
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds
2–9 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds
7–12 May
4.96 out of 5 average rating, 68 reviews
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
3 bedrooms, 3 beds
7–14 Aug
5.0 out of 5 average rating, 8 reviews
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
2 queen beds
16–21 Aug
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms
1–8 Aug
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds
1–8 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds
2–7 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds
7–12 Sept
4.96 out of 5 average rating, 46 reviews
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds
1–8 Aug
4.92 out of 5 average rating, 26 reviews
Luxe
Home in Islamorada
Private Beach / Pickleball Court and Tiki Bar
6 bedrooms, 8 king beds
16–23 Aug