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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
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 50 reviews
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.92 out of 5 average rating, 50 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
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
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
4.92 out of 5 average rating, 26 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
Home in Islamorada
Bayview Beautiful townhouse in Islamorada, FL KEYS
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 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, 60 reviews
Serviced apartment in Islamorada
Suites Near Lignumvitae Key! Parking, Breakfast!
1 bedroom, 1 king bed, 1 bathroom
22–27 Aug
New place to stay
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 Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Key Colony Beach
Exquisite Oceanfront Paradise - Key Colony Beach
1 bed, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 220 reviews
Guest favourite
Apartment in Tavernier
Captains Quarters Ocean Pointe 4405
2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
4.87 out of 5 average rating, 90 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Flat in Islamorada
Bungalows King Bed
1 bed, 1 bathroom
15–20 Aug
4.86 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 103 reviews
Guest favourite
Apartment in Tavernier
Sea View and Sunrise Ocean Pointe 2412 2BA/2BR
2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
4.96 out of 5 average rating, 55 reviews