Islamorada Vacation Packages

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Your Islamorada Vacation

The laid-back lifestyle and spectacular views are just the beginning of the things Islamorada has to offer. Enjoy the sights and sounds of this captivating city the way you want with a customized Islamorada vacation package. You'll want to do some exploring during your trip to Islamorada. Make time for popular attractions like Theater of the Sea, Bud n Marys Dive Center and Founders Park. Check out Expedia's wide range of travel options and start organizing your dream vacation to Islamorada today.

Top Islamorada Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul. 14 - Jul. 20
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Jul. 1 - Jul. 4
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (1,002 reviews)
Beach was clean, compare to other resorts with private beach in miami!!! However we notice that all pool area were small for hotel quality 😉

Reviewed on May 13, 2024

Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
Save 100% on your flight
per person
Jul. 17 - Jul. 21
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (500 reviews)
This is a beautiful hotel with great staff! The area is perfect for walking with great restaurants.

Reviewed on May 6, 2024

May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jun. 25 - Jul. 2
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (1,273 reviews)
Excellent place I will stay again

Reviewed on May 12, 2024

Amazing Apartments at H Beach House

Amazing Apartments at H Beach House

3.5 out of 5
Hollywood Beach
Save 100% on your flight
per person
Jun. 25 - Jul. 2
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (8 reviews)
We are very disappointed because the last 2 days of our stay a scaffolding was hunging for our full, out side balcony, to do maintenance of which we were not informed in any way, a jackhammer was drilled into the foundation, which greatly disturbed our peace and quiet due to the enormous noise and our privacy. We have a video recording of that and we believe we should receive compensation for this. We were literally chased out of our apartment.

Reviewed on May 3, 2024

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 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.

Islamorada Hotel Deals

Cheeca Lodge & Spa
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $409 per night from Jun. 10 to Jun. 11
CA $409
CA $545 total
includes taxes & fees
Jun 10 - Jun 11
8.8/10 Excellent! (1,006 reviews)
"Beautiful property"

Reviewed on May 13, 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 CA $286 per night from May 21 to May 22
CA $286
CA $376 total
includes taxes & fees
May 21 - May 22
8.8/10 Excellent! (1,313 reviews)
"Loved"

Reviewed on May 11, 2024

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $425 per night from May 21 to May 22
CA $425
CA $553 total
includes taxes & fees
May 21 - May 22
8.8/10 Excellent! (1,247 reviews)
"The resort was absolutely beautiful and the staff go above and beyond. The room key bracelets were so convenient and so cute to wear. We even got to keep them as souvenirs. Definitely the best place I have ever stayed."

Reviewed on May 12, 2024

Amara Cay Resort
See all 2,125 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Frequently asked questions

How much does an Islamorada vacation package cost?
The cheapest Islamorada vacation package is CA $786, so your dream vacation can become a reality — without breaking the bank. Combine flights, hotels, car rentals and more to tailor make a package suited to your traveling 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 vacation 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 Theater of the Sea, Bud n Marys Dive Center and Annes Beach. Stay near these popular sights and make sightseeing a breeze.
What are the top hotels in Islamorada?
Travelers visiting Islamorada often make a reservation at Postcard Inn Beach Resort & Marina or Amara Cay Resort. These options are in Venetian Shores. Another interesting neighborhood 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 vacation?
Travelers 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 vacation package is the most convenient way to organize 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 vacation 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 vacation package?
Plans can change suddenly, so yes, you can. You may be able to cancel or change your Islamorada vacation 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.

Discover the most popular places to visit in Islamorada

Image for Theater of the Sea

Theater of the Sea

4/5(6 reviews)

Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.

Theater of the Sea
Image for Anne's Beach

Anne's Beach

4/5(14 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
Image for Founders 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

What to do in Islamorada

Image for Salty Keys Snorkel and Sandbar Activity

Salty Keys Snorkel and Sandbar Activity

CA $217
Per adult
Salty Keys Snorkel and Sandbar Activity
Image for Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

CA $508
Per adult
Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours
Image for Private 2 hour Mangrove Ecotour

Private 2 hour Mangrove Ecotour

CA $616
Per adult
Private 2 hour Mangrove Ecotour
See all activities in Islamorada

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.