Islamorada Holidays
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Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Matecumbe
6 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing.
Top hotels in Islamorada
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 3.672.227 ₫ per night from 30 Nov to 1 Dec
3.672.227 ₫
5.614.316 ₫ total
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (1,582 reviews)
Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms.
Reviewed on 17 Nov 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 6.827.758 ₫ per night from 1 Dec to 2 Dec
6.827.758 ₫
9.460.795 ₫ total
1 Dec - 2 Dec
includes taxes & fees
9/10 Wonderful! (1,271 reviews)
Nice place
Reviewed on 22 Nov 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 4.074.907 ₫ per night from 30 Nov to 1 Dec
4.074.907 ₫
6.334.180 ₫ total
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,258 reviews)
Rooms were clean, landscape was beautiful, staff was friendly. Access to the (2) other resorts were a plus. Would stay again.
Reviewed on 17 Nov 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Anne's Beach
4.5/5(3 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.
Founders Park
3.5/5(2 reviews)
Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
