Islamorada Holidays
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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.
Venetian Shores
Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Islamorada County Park and Founders Park.
Lower Matecumbe Beach
While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.
Seabreeze Trailer Park
While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like Founders Park and Islamorada County Park.
Islamorada Beach Holiday
Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. 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 kilometres from the town centre. 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 holiday homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour 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.
Top hotels in Islamorada
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
Rp2.640.727
Rp4.266.901 total
2 Sept - 3 Sept
includes taxes & fees
Chesapeake Beach Resort
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
Rp2.677.059
Rp4.008.610 total
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,773 reviews)
"I like the view of the ocean and everything"
Reviewed on 26 Aug 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
Rp2.978.793
Rp4.647.225 total
30 Aug - 31 Aug
includes taxes & fees
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
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.
Florida Keys Brewing Co.
9.2/10 (520 reviews)
The Upper Keys' first microbrewery infuses local flavours 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.
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 fossilised reef.
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.
Robbie’s of Islamorada
8.4/10 (15 reviews)
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
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 specialised dog parks.
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.
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 colours as the sun sinks into the Atlantic Ocean.
What to do in Islamorada
Mangroves and Manatees - Guided Kayak Eco Tour
Rp1.232.409
per adult
92% of travellers recommend
Explore the Mangrove Creeks with an ALL Day Tandem Kayak Rental
Rp1.189.585
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Rp875.189
per adult
80% of travellers recommend
Frequently asked questions
How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We'd recommend booking an Islamorada holiday 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 neighbourhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a holiday 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 Theatre of the Sea and Hurricane Monument, or take the path less traveled, there's plenty to see and do on your Islamorada holiday.
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 holiday package well in advance.
Is it cheaper to book an Islamorada holiday as a package?
You can enjoy significant savings on your Islamorada escape by booking a customised holiday 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 holiday 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?
- 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.
- 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.
- 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.
- Combine your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Islamorada holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
