Islamorada Holidays from AU$814

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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!

The Latest Islamorada Holiday Deals

Price found within the past 48 hours. Click for updated prices.
EB Hotel Miami

EB Hotel Miami

4 out of 5
per person
14 Apr - 17 Apr
found 10 hours ago
Return direct flight included
Montreal (YUL) to Miami (MIA)
9.4/10 Exceptional! (2,274 reviews)
Tha clerk at check in was super friendly and helpful.

Reviewed on 17 Feb. 2025

Hotel AKA Brickell

Hotel AKA Brickell

5 out of 5
Downtown Miami
Save 100% on your flight
per person
14 Apr - 17 Apr
found 10 hours ago
Return direct flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (818 reviews)
Stayed for the weekend of Valentines Day and i honestly could’ve have asked for a better location to stay. Super friendly and helpful staff. Area was clean and easy to get around. Pool was nice and so was the locbby. Only thing I’d comment on is making the gym a little better machines and weight wise.

Reviewed on 16 Feb. 2025

The Standard Spa Miami Beach

The Standard Spa Miami Beach

4 out of 5
Venetian Islands
Save 100% on your flight
per person
14 Apr - 17 Apr
found 10 hours ago
Return direct flight included
Montreal (YUL) to Miami (MIA)
8.8/10 Excellent! (1,000 reviews)
Love meeting new people and also people I already knew while lounging by the pool

Reviewed on 11 Feb. 2025

Dream South Beach, by Hyatt

Dream South Beach, by Hyatt

4 out of 5
South Beach
per person
14 Apr - 17 Apr
found 10 hours ago
Return direct flight included
Montreal (YUL) to Miami (MIA)
8.4/10 Very Good! (1,005 reviews)
Comfy rooms. Great location. Convenient food options.

Reviewed on 11 Feb. 2025

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

5 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

Take a break from life's daily stresses and relax on your Islamorada holiday. Few things are more rejuvenating than a cool ocean breeze and the sound of waves lapping at the shore. Plan your trip to Islamorada the quick and easy way by locking in one of our Islamorada packages. Many people opt to base themselves near Anne's Beach, a must-see only 16 kilometres from the downtown area.

Things You Should Know About Islamorada

  • Spend your getaway by the water and let the stresses of daily life drift away with the ocean breeze. Check out our Islamorada beach hotels and indulge in a little beachside bliss.
  • Have a look at Angler's Reef Resort by KeysCaribbean and Blue Water Retreat by RedAwning. These private holiday homes might just be ideal for your stay in Islamorada.
  • Roughly 7 100 people reside in Islamorada. If you're after tips about what to see and do in this area, why not strike up a conversation with some of the friendly locals? Our Islamorada things to do page is also a handy source of information.
  • Islamorada holiday deals are a terrific way to save on exciting experiences. Some ideas, including Theatre of the Sea, Founders Park and Anne's Beach, belong at the very top of your sightseeing list.

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
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$845 per night from 20 Feb to 21 Feb
AU$845
includes taxes & fees
20 Feb - 21 Feb
9/10 Wonderful! (1,401 reviews)
"Loved it Beach front was perfect"

Reviewed on 14 Feb. 2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$647 per night from 24 Feb to 25 Feb
AU$647
includes taxes & fees
24 Feb - 25 Feb
8.8/10 Excellent! (1,209 reviews)
"We really enjoyed our stay at Amara Cay Resort. Wonderful staff, very helpful and knowledgeable. Gorgeous location on the Atlantic side of Islamorada. Beautiful pool area and tiki bar."

Reviewed on 12 Feb. 2025

Amara Cay 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$683 per night from 23 Feb to 24 Feb
AU$683
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (1,029 reviews)
Cheeca Lodge
"We had an amazing relaxing trip . It is beautiful and impeccably maintained. Anna at the front desk was so nice. Maureen the concierge was so helpful and sweet. Cassandra was our favorite waitress. We will definitely go back,"

Reviewed on 10 Feb. 2025

Cheeca Lodge & Spa
See all 2,245 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
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination from AU$814 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.

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

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Sunset Drive Beach

What to do in Islamorada

Day Tour Glass Bottom Boat In Islamorada

Day Tour Glass Bottom Boat In Islamorada

AU$129
per adult
Day Tour Glass Bottom Boat In Islamorada
Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

AU$235
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Golden Glare Fishing Charter with Experienced Captain

Golden Glare Fishing Charter with Experienced Captain

AU$965
per traveller
Golden Glare Fishing Charter with Experienced Captain
See all activities in Islamorada
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.