Islamorada Holidays

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Your Islamorada Holiday

With one of our holiday packages to Islamorada, you'll have infinite opportunities for fun and excitement. There's a lot to enjoy, including its laid-back lifestyle and spectacular views. If sightseeing is part of the plan during your trip to Islamorada, visit well-known attractions like Theatre of the Sea, Bud n Marys Dive Centre and Founders Park. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Islamorada holiday plans in motion!

Our guide on 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

Islamorada Holiday

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.

Islamorada Essential Information

Language
English
Currency
U.S dollars
Population
7,100
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Theatre of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park

Our pick of the best Islamorada Hotel Deals

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 AU$326 per night from 10 Aug to 11 Aug
AU$326
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,487 reviews)
"Clean and comfortable with breakfast on site. Close activities and a few restaurants within walking distance"

Reviewed on 3 Aug. 2025

Chesapeake Beach 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 AU$398 per night from 4 Sept to 5 Sept
AU$398
4 Sept - 5 Sept
includes taxes & fees
9/10 Wonderful! (1,143 reviews)
"Teh staff goes above and beyond to make your stay special. The customer service is first class."

Reviewed on 4 Aug. 2025

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$466 per night from 12 Aug to 13 Aug
AU$466
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Awesome Resort, great staff and helpful management. Definitely will be coming back here."

Reviewed on 1 Aug. 2025

Islander Resort
See all 2,183 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
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beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Islamorada

Anne's Beach

Anne's Beach

If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.

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

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

What to do in Islamorada

Islamorada Florida Sunset Cruise Tour

Islamorada Florida Sunset Cruise Tour

AU$130
per adult
Islamorada Florida Sunset Cruise Tour
Explore the Mangrove Creeks with an All Day Kayak Rental

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

AU$72
per adult
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

AU$227
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
See all activities in Islamorada

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?

  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 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.