Islamorada Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 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
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₩279,319 per night from Jan 6 to Jan 7
₩279,319
₩397,341 total
Jan 6 - Jan 7, 2026
includes taxes & fees
9.2/10 Wonderful! (1,599 reviews)
The breakfasts are great
Reviewed on Dec 19, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
The price is ₩348,060 per night from Jan 4 to Jan 5
₩348,060
₩489,643 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
I would give this hotel one the highest ratings for my most recent stays in the area. The views were spectacular. All of the staff were very friendly and helpful. Very very minor thing was the condition of the furniture and electrical sockets weren't the best quality but I just loved everything else ...
Reviewed on Dec 16, 2025
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is ₩589,519 per night from Jan 4 to Jan 5
₩589,519
₩771,265 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9.2/10 Wonderful! (1,270 reviews)
Ate dinner at the Asian restaurant Nikki- the Chilean Seabass was delicious andmelted with every bite. And service was good
Reviewed on Dec 18, 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?
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
