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

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

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.

Top hotels in Islamorada

Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is S$426 per night from 19 Dec to 20 Dec
S$426
includes taxes & fees
19 Dec - 20 Dec
8.8/10 Excellent! (1,195 reviews)
A great resort in the middle keys
"The resort, while not brand new, is immaculate and well appointed throughout."

Reviewed on 17 Dec,2024

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 S$490 per night from 19 Dec to 20 Dec
S$490
includes taxes & fees
19 Dec - 20 Dec
9/10 Wonderful! (1,006 reviews)
"Magnificent resort. Quiet and peaceful!"

Reviewed on 16 Dec,2024

Cheeca Lodge & Spa
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 S$385 per night from 20 Dec to 21 Dec
S$385
includes taxes & fees
20 Dec - 21 Dec
9/10 Wonderful! (1,385 reviews)
"Stay one night in December for a half marathon. Room was clean and comfortable"

Reviewed on 14 Dec,2024

Chesapeake Beach Resort
See all 2,217 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?
The cheapest Islamorada holiday package is , so your dream holiday can become a reality — without breaking the bank. Combine flights, hotels, car rentals and more to tailor make a package suited to your travelling style.
How do I get a cheap travel package to Islamorada?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you cash too. An Islamorada holiday package makes it easy to create your dream adventure. With more than 550 airlines across the world to select from, finding convenient flights that suit your schedule won’t be a challenge. On top of that, we’ve got over 1,000,000 hotels globally to select from. Now that’s choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Islamorada?
A getaway to Islamorada isn’t complete without checking out Theatre of the Sea, Bud n Marys Dive Centre and Annes Beach. Stay near these popular sights and make sightseeing a breeze.
What are the top hotels in Islamorada?
Travellers visiting Islamorada often make a reservation at Postcard Inn Beach Resort & Marina or Amara Cay Resort. These options are in Venetian Shores. Another interesting neighbourhood is Lower Matecumbe Beach. Chesapeake Beach Resort and Islander Resort are popular choices in this part of town.
How far in advance should I book my Islamorada holiday?
Travellers are usually able to browse international flights on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it’s still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Islamorada travel package include?
It comes down to what type of trip you’re planning. Islamorada travel deals can include hotels, car rentals and flights. You can mix and match to create the bundle that works for you! You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking an Islamorada travel package?
Bundling your bookings into an Islamorada holiday package is the most convenient way to organise your trip. Not only that, you’ll save big just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with an Islamorada Expedia holiday package?
Yes, you can. We have more than 550 airline partners across the globe, so fly with the carrier that matches your travel preferences.
If I'm not able to travel, can I cancel my Islamorada holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or change your Islamorada holiday package for free within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your car rental company, hotel or airline may charge additional fees. Want more information? Look up our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Popular places to visit

Founders Park showing modern architecture, theatre scenes and a park

Founders Park

3.5/5(2 reviews)

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
History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum

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

S$108
per adult
Day Tour Glass Bottom Boat In Islamorada
Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

S$197
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Robbie's Island Escape & Miami Sightseeing Cruise Combo

Miami to Robbies Islamorada Island Escape & Miami Boat Tour Combo

S$101
per adult
Miami to Robbies Islamorada Island Escape & Miami Boat Tour Combo
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.