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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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4.98 out of 5 average rating, 60 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
24–29 Jul
New place to stay
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
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, 53 reviews
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
25 Jul – 1 Aug
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, 14 reviews
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 1 bathroom
7–12 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 112 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
20–25 Jul
4.91 out of 5 average rating, 34 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
5.0 out of 5 average rating, 85 reviews
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
5 bedrooms, 9 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 25 reviews
Guest favourite
Home in Islamorada
Summer-Fall Super Discounts- Check Availability!
4 bedrooms, 5 beds, 4.5 bathrooms
13–20 Aug
5.0 out of 5 average rating, 7 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, 68 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
18–23 Jul
New place to stay
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
24–31 Jul
4.96 out of 5 average rating, 25 reviews
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
Home in Key Largo
The charm
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 12 reviews