Islamorada Vacations
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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
5 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.
Find the Best Islamorada Vacation Packages
Islamorada Hotel Deals
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AED 840 per night from Feb 11 to Feb 12
AED 840
AED 1,152 total
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (1,665 reviews)
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.
Reviewed on 3 February 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AED 1,032 per night from Feb 10 to Feb 11
AED 1,032
AED 1,430 total
10 Feb - 11 Feb
includes taxes & fees
9.2/10 Wonderful! (1,294 reviews)
We stayed in Premiere ocean front king. The weather was unusually cold and windy so we didn't get to experience the resort as we had hoped. The staff at restaurants were very courteous and service prompt. Beach is lovely -- although not a natural sand beach. Gym could have been larger. We found spa ...
Reviewed on 4 February 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is AED 887 per night from Feb 11 to Feb 12
AED 887
AED 1,267 total
11 Feb - 12 Feb
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
All good, nice bartender inside downstairs, and easy walk to fish and eat
Reviewed on 5 February 2026
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.
Discover the most popular places to visit in Islamorada
History of Diving Museum
You can spend an afternoon exploring the galleries in History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.
Matecumbe United Methodist Church
After visiting Matecumbe United Methodist Church, make a plan to see the other sights and activities in Islamorada. Discover the beautiful sunsets in this family-friendly area, or enjoy its fishing spots.
Robbie’s of Islamorada
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
