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 Robbie’s of Islamorada 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 5.230.800 ₫ per night from 8 Jun to 9 Jun
5.230.800 ₫
7.366.555 ₫ total
8 Jun - 9 Jun
includes taxes & fees
9.2/10 Wonderful! (1,738 reviews)
"I had a wonderful time on my getaway. The view from my room was beautiful. Everything was quite and pleasant perfect for a family. Everyone was polite, and the breakfast was delicious. The view of the breakfast was phenomenal."
Reviewed on 26 May 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 5.242.655 ₫ per night from 3 Jun to 4 Jun
5.242.655 ₫
7.824.597 ₫ total
3 Jun - 4 Jun
includes taxes & fees
9.2/10 Wonderful! (1,315 reviews)
"amenities were great, clean hotel, lots of fun."
Reviewed on 24 May 2026
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is 6.072.422 ₫ per night from 21 Jun to 22 Jun
6.072.422 ₫
8.610.505 ₫ total
21 Jun - 22 Jun
includes taxes & fees
9.4/10 Exceptional! (1,022 reviews)
"Amazing!! Nothing bad to say at all"
Reviewed on 26 May 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.
Popular places to visit
Bud n' Mary's Dive Center
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
Founders Park
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.
Anne's Beach
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.
