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
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.
Find the Best Islamorada Vacation Packages
Islamorada Beach Vacation
Relax along the shoreline and feel the wind through your hair during your Islamorada vacation. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometers from the town center. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.
Things You Should Know About Islamorada
- Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
- If you're searching for lots of room to spread out and relax, Islamorada private vacation homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbor and Bud N' Mary's Fishing Marina will fit the bill.
- Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.
Islamorada Hotel Deals
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩138,283 per night from Sep 30 to Oct 1
₩138,283
₩249,852 total
Sep 30 - Oct 1
includes taxes & fees
9/10 Wonderful! (1,202 reviews)
"We weren’t allowed to use the bikes because of the rain, but it rained all weekend anyway."
Reviewed on Sep 16, 2025
Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩171,178 per night from Sep 21 to Sep 22
₩171,178
₩271,145 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (1,531 reviews)
"Very clean property, good breakfast included and the views are spectacular!! Beautiful beach location!! Would go back anytime!!"
Reviewed on Sep 17, 2025
Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₩234,767 per night from Sep 22 to Sep 23
₩234,767
₩356,833 total
Sep 22 - Sep 23
includes taxes & fees
8.8/10 Excellent! (1,250 reviews)
"Great hotel with a perfect location and friendly staff."
Reviewed on Sep 13, 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.
Discover the most popular places to visit in Islamorada
Sunset Drive Beach
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
