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
Islamorada showing a beach bar

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 Florida Keys Brewing Co. are top sights worth seeing.

Find hotels in Matecumbe

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

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NT$5,965 per night from Aug 13 to Aug 14
NT$5,965
NT$8,734 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Restaurant options are great, they offer Italian, sushi, beachside dining and an American restaurant. There are also poolside versions of their regular American restaurant. The amenities are phenomenal, including pier fishing, bikes, games and various water sport activities. There are plenty of other ..."

Reviewed on 2025/8/2

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NT$4,527 per night from Aug 5 to Aug 6
NT$4,527
NT$6,779 total
Aug 5 - Aug 6
includes taxes & fees
9/10 Wonderful! (1,477 reviews)
"It was new, loved the balcony. Beach sports were nice but needed more lifejacket sizes. Pool amenities were great. Breakfast was good."

Reviewed on 2025/7/30

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NT$6,234 per night from Aug 11 to Aug 12
NT$6,234
NT$9,037 total
Aug 11 - Aug 12
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"This place was amazing! It definitely had a resort feel and was very clean. Even though the beaches aren't the normal tropic island beaches everthing inside the resort made you feel you were on an island. The staff was very helpful and friendly. The parking was free and right outside our room. The ..."

Reviewed on 2025/8/1

Islander Resort
See all 2,189 properties in Islamorada
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 featuring a bridge

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.

Anne's Beach
Founders Park featuring theater scenes, a garden and modern architecture

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.

Founders Park
Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.

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.

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