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 Robbie’s of Islamorada 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 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$6,252 per night from May 31 to Jun 1
NT$6,252
NT$9,330 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,309 reviews)
"Good"
Reviewed on 2026/5/29
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$6,237 per night from Jun 2 to Jun 3
NT$6,237
NT$8,784 total
Jun 2 - Jun 3
includes taxes & fees
9.2/10 Wonderful! (1,728 reviews)
"Todo muy bueno"
Reviewed on 2026/5/29
Islander Resort
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is NT$6,831 per night from Jun 8 to Jun 9
NT$6,831
NT$9,805 total
Jun 8 - Jun 9
includes taxes & fees
9.4/10 Exceptional! (1,020 reviews)
"We went for our anniversary and this property was paradise. Just beautiful and steps from the water. Plenty activities to do Bike riding/mini golf/fishing etc. The staff was very friendly and sunrise 🌅"
Reviewed on 2026/5/27
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
Founders Park
4.5/5(139 reviews)
Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.
Anne's Beach
3.5/5(141 reviews)
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.
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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.
