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 Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

Find the Best Islamorada Vacation Packages

Islamorada Hotel Deals

Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AED 729 per night from Apr 30 to May 1
AED 729
AED 1,027 total
includes taxes & fees
30 Apr - 1 May
9/10 Wonderful! (1,384 reviews)
"The property was clean and and everything was well maintained."

Reviewed on 12 April 2025

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AED 996 per night from May 12 to May 13
AED 996
AED 1,364 total
includes taxes & fees
12 May - 13 May
8.8/10 Excellent! (12 reviews)
"Our stay here was great for the most part! 2 hicupps; the room we were assigned, the shower door leaked all over the floor! However, when letting the fromt desk know, they upgradedus to a room right off the beach ground floor so we were very happy!"

Reviewed on 12 April 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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 AED 879 per night from May 13 to May 14
AED 879
AED 1,237 total
includes taxes & fees
13 May - 14 May
9/10 Wonderful! (1,059 reviews)
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Reviewed on 12 April 2025

Cheeca Lodge & Spa
See all 2,198 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.

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 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.

Discover the most popular places to visit in Islamorada

Anne\'s Beach featuring a bridge

Anne's Beach

3.5/5(139 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.

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

Founders Park

4.5/5(137 reviews)

Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander the seaside and beautiful beaches in this family-friendly area.

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.