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
Islamorada showing a beach bar

Matecumbe

7 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 hotel + flight trips in Matecumbe

Islamorada Beach Vacation

Take a break from life's daily stresses and relax on your Islamorada vacation. 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 vacation 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 vacation deals are a terrific way to save on exciting experiences. Some ideas, including Theater of the Sea, Founders Park and Anne's Beach, belong at the very top of your sightseeing list.

Top hotels in Islamorada

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 HK$2,047 per night from 12 Jan to 13 Jan
HK$2,047
HK$2,828 total
includes taxes & fees
12 Jan - 13 Jan
9/10 Wonderful! (1,011 reviews)
"Beautiful property!"

Reviewed on 3 Jan 2025

Cheeca Lodge & Spa
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 HK$2,012 per night from 20 Jan to 21 Jan
HK$2,012
HK$2,780 total
includes taxes & fees
20 Jan - 21 Jan
8.8/10 Excellent! (1,214 reviews)
"Everything was good at this property."

Reviewed on 4 Jan 2025

Amara Cay Resort
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 HK$1,236 per night from 8 Jan to 9 Jan
HK$1,236
HK$1,780 total
includes taxes & fees
8 Jan - 9 Jan
9/10 Wonderful! (1,386 reviews)
"Really lovely property, nice updated room. Bathroom could use improved lighting for mirrors, but overall very nice! Front desk staff seemed a bit frazzled & slightly unprofessional, but some customer service training could easily improve that. The bar/breakfast service and staff were very good! Cleaning ..."

Reviewed on 3 Jan 2025

Chesapeake Beach Resort
See all 2,226 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 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.

What to do in Islamorada

Robbie's Island Escape & Miami Sightseeing Cruise Combo

Miami to Robbies Islamorada Island Escape & Miami Boat Tour Combo

HK$583
per adult
Miami to Robbies Islamorada Island Escape & Miami Boat Tour Combo
Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

HK$1,142
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Day Tour Glass Bottom Boat In Islamorada

Day Tour Glass Bottom Boat In Islamorada

HK$624
per adult
Day Tour Glass Bottom Boat In Islamorada
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.