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 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 NT$5,355 per night from Jan 7 to Jan 8
NT$5,355
NT$7,796 total
Jan 7 - Jan 8
includes taxes & fees
9.2/10 Wonderful! (1,625 reviews)
The resort is a great family friendly atmosphere. The staff was extremely hospitable. The beach is clean and lots of fun activities to do. Only wish we had more time!
Reviewed on 2026/1/6
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$9,074 per night from Jan 20 to Jan 21
NT$9,074
NT$12,299 total
Jan 20 - Jan 21
includes taxes & fees
8.8/10 Excellent! (122 reviews)
No balcony. We walked out right to the beach. IT WAS EVEN BETTER!!
Reviewed on 2025/12/27
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$9,416 per night from Jan 29 to Jan 30
NT$9,416
NT$12,896 total
Jan 29 - Jan 30
includes taxes & fees
9.2/10 Wonderful! (1,284 reviews)
Fantastic resort, will definitely be heading back!
Reviewed on 2026/1/4
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
Anne's Beach
If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.
Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
Founders Park
Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.
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- Beach Vacation Packages Duck Key
- Eco Pond
- Jimmy Johnson's Big Chill
- Coral Castle Museum
- Visit Venetian Shores
- Homestead Town Square
- Pa-Hay-Okee Lookout Tower
- Founders Park
- Fasulo Park
- Loren Roberts Park
- Flamingo Visitor Center
- Roby George Park
- Homestead Bayfront Park
- Sunset Drive Beach
- Everglades National Park
- History of Diving Museum
- Ernest F. Coe Visitor Center
- Mayor Roscoe Warren Municipal Park
- Florida Keys Brewing Co.
- Dante Fascell Visitor Center
- Buttonwood Canal
- Shark River Slough
- Seven Mile Bridge
- Naranja Vacations
- Visit Pirates Cove
- Visit Duck Key
- Visit Long Key
- Homestead Air Force Base
- Keys Gate Golf Club
- Visit Key Largo
- Anne's Beach
- Marinelab Undersea Laboratory
- Homestead Miami Speedway
- Anhinga Trail
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
