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 Anne's Beach are top sights worth seeing.
Top hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 3.137.078 ₫ per night from 16 Oct to 17 Oct
3.137.078 ₫
5.308.780 ₫ total
16 Oct - 17 Oct
includes taxes & fees
9/10 Wonderful! (1,214 reviews)
"Staff was extremely accommodating, Property is stunning with numerous activities."
Reviewed on 6 Oct 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 3.981.980 ₫ per night from 12 Oct to 13 Oct
3.981.980 ₫
5.962.557 ₫ total
12 Oct - 13 Oct
includes taxes & fees
9.2/10 Wonderful! (1,531 reviews)
"Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect ..."
Reviewed on 4 Oct 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 3.539.598 ₫ per night from 20 Oct to 21 Oct
3.539.598 ₫
5.731.226 ₫ total
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (1,253 reviews)
"We had a room with an ocean view and it was great. There was a beautiful double rainbow over the water one of the days we were there."
Reviewed on 4 Oct 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.
