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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
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
Flat in Islamorada
Poolside 2 queen Apartment
4.8 out of 5 average rating, 50 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
5.0 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 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
Guest favourite
Home in Islamorada
Boat slip included August-November 2026!
4.92 out of 5 average rating, 50 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 5 Sept
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
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
Serviced apartment in Islamorada
Suites Near Lignumvitae Key! Parking, Breakfast!
New place to stay, 1 bedroom, 1 bathroom
22–27 Aug
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Guest favourite
Apartment in Tavernier
Captains Quarters Ocean Pointe 4405
4.87 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 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 Islamorada
Bayview Beautiful townhouse in Islamorada, FL KEYS
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
Top guest favourite
Apartment in Key Colony Beach
Exquisite Oceanfront Paradise - Key Colony Beach
4.91 out of 5 average rating, 220 reviews, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Apartment in Tavernier
Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool
4.94 out of 5 average rating, 16 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4.87 out of 5 average rating, 46 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
4.93 out of 5 average rating, 387 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug