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
A pier extending into calm waters with a covered seating area and a sandy beach.

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.

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A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores might not have many top sights, but Rain Barrel Village and Founders Park are two attractions nearby that you can check out.

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A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.

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A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.

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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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
NT$6,353
NT$9,482 total
Oct 14 - Oct 15
includes taxes & fees
9.2/10 Wonderful! (1,476 reviews)
"The suite is advertised as 804 sq ft with 2 queen beds and a sitting area. It's just one rectangular room without any separate areas, and there are no doors either; the size of the room is about 500sqft, and the extra 300sq ft is probably the bathroom and outside balcony. But the location of the ..."

Reviewed on 2026/10/13

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
NT$4,822
NT$7,221 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,800 reviews)
"Lovely place to stay in Islamorada. Beach and pools were great. Fantastic breakfast included with made to order omelettes. Parking was available. We stayed in the most basic room which was in the building by the office so we could hear traffic from the Overseas Highway but was it pretty quiet inside ..."

Reviewed on 2026/10/12

Chesapeake Beach Resort
Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
NT$6,640
NT$9,804 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (1,139 reviews)
"Fabulous bedroom cozy bed and awesome hot shower. Couch was sorta cheap and no fridge but we loved the ice maker and kitchenette. We loved the pool and the staff. Weak drinks but good food. The feeling there is soooo great. Will 100% come back."

Reviewed on 2026/10/13

Islander Resort
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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.

Stay near popular Islamorada attractions

A wooden deck with benches overlooking a clear blue sea.

Anne's Beach

7.8/10 (597 reviews)
Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
The Upper Keys' first microbrewery infuses local flavors like Key lime and honey into its craft beers. Sip seasonal brews in the vibrant taproom or lush beer garden while enjoying local art and live music.
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An archaeological site with stone structures and metal machinery.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Walk through ancient coral walls rising eight feet high in this former limestone quarry turned state park. Ranger-guided tours reveal the fascinating geological history preserved in the fossilized reef.
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A building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)
Discover 4,000 years of underwater exploration at this unique museum featuring diving helmets from around the world. Explore exhibits showcasing the evolution of diving technology from ancient to modern times.
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Islamorada County Park

8.8/10 (198 reviews)
This 40-acre waterfront retreat offers a bayfront beach, marina, and scenic trails for active relaxation. Enjoy a refreshing swim in the pool or bring your four-legged friend to the specialized dog parks.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
The Florida Keys' first distillery crafts award-winning spirits and beers capturing the island's essence. Enjoy tastings in their relaxed taproom or pet-friendly garden with pub-style food available.
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Sunset Drive Beach

9.0/10 (91 reviews)
This secluded stretch of Islamorada shoreline offers a peaceful retreat from Florida's busier beaches. Watch the sky transform into a canvas of colors as the sun sinks into the Atlantic Ocean.
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Rain Barrel Village

You can enjoy retail therapy at Rain Barrel Village during your stay in Islamorada. Take in the entertainment choices and beautiful sunsets in this relaxing area.
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Frequently asked questions

How much does an Islamorada vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Islamorada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Islamorada?
You can generally find lower prices and greater availability in September, October and November. Browse our cheap Islamorada vacation packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We'd recommend booking an Islamorada vacation for at least 3 days. This will give you enough time to visit top attractions such as Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, and explore neighborhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a vacation package to Islamorada?
Islamorada has all the ingredients you need for a fantastic getaway — walking trails, views and family-friendly attractions are just the start. Whether you'd like to check out attractions such as Theater of the Sea and Hurricane Monument, or take the path less traveled, there's plenty to see and do on your Islamorada vacation.
How to find the best Islamorada package deals?
Use Expedia's filter tool to help you find some tempting Islamorada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Islamorada package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Islamorada vacation as a package?
You can enjoy significant savings on your Islamorada escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Islamorada?
If you're considering a spur-of-the-moment Islamorada getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Islamorada?
  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Islamorada.
  2. Set your budget: Factor in expenses like food, flights and transportation when working out how much to save for your trip to Islamorada. Then, select a hotel that works with your budget, whether that's a low-cost option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend exploring Islamorada. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Islamorada vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.