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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Apartment in Islamorada
Luxury condo with boat slip overlooking the bay
3 bedrooms, 3 beds, 2.5 private bathrooms
15–22 Aug
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5.0 out of 5 average rating, 36 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
3–9 Aug
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
4.96 out of 5 average rating, 69 reviews, 3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 216 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
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
25–30 Aug
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
Fishing Getaway | Dock, Pool & Sunrise
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 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
Top guest favourite
Home in Tavernier
Superb Keys home w/heated pool
4.96 out of 5 average rating, 25 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–18 Sept
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 1 bed, 3 bathrooms
9–14 Aug
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 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
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
22–29 Aug
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
2 queen beds, 1 bathroom
16–21 Aug
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
2–7 Aug
Guest favourite
Home in Key Largo
3BR Oceanview Oasis: Pool, Spa & Elevator
4.8 out of 5 average rating, 45 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept