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.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jun. 1 - Jun. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.4/10 Exceptional! (1,349 reviews)
This is a hidden jewel among the many overrated and over priced hotels/motels nearby. It was very clean and the staff are remarkable.

Reviewed on Apr. 28, 2025

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. 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,216 reviews)
Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down.

Reviewed on Apr. 30, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
It was a great family resort

Reviewed on Apr. 23, 2025

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.

Reviewed on Mar. 17, 2025

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

Gold Coast Beach Vacation

Take a break from the stresses of everyday life and relax on your Gold Coast vacation. There's nothing more invigorating than the smell of salty sea air and the sound of waves crashing onto the shore. Organize your trip to Gold Coast the quick and easy way by locking in one of our Gold Coast packages. Many travelers decide to spend their nights close to Golden Beach, a must-see just 0.2 miles (0.3 km) from the city center.

Ready to book your vacation to Islamorada?

 

Choose your dates

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 CA $289 per night from May 1 to May 2
CA $289
CA $403 total
includes taxes & fees
May 1 - May 2
9/10 Wonderful! (1,430 reviews)
"Good for the price and convenient for fishing trips. No frills, clean rooms good location."

Reviewed on Apr. 28, 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 CA $375 per night from May 20 to May 21
CA $375
CA $515 total
includes taxes & fees
May 20 - May 21
9/10 Wonderful! (1,066 reviews)
"Great spot. Restaurants on Location."

Reviewed on Apr. 24, 2025

Cheeca Lodge & Spa
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $375 per night from May 12 to May 13
CA $375
CA $514 total
includes taxes & fees
May 12 - May 13
8.8/10 Excellent! (17 reviews)
"We loved the hotel. Perfect weekend getaway with our dog. It really is pet friendly and everyone is super nice. Loved all the dinning options as well as the amount of different spaces to be at. Definitely will be coming back!"

Reviewed on Apr. 19, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Islamorada vacation package cost?
You can pick up a vacation package to this top destination from CA $427 on Expedia. However, how much your vacation to Islamorada costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Islamorada?
If you’d like to score a cheap Islamorada vacation package, consider travelling in September, October and November. You’ll typically find better rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Islamorada?
To fully enjoy your Islamorada vacation, we recommend staying for 3 days. Divide your time between discovering Islamorada County Park, Indian Key Historic State Park and other leading sights, as well as exploring neighbourhoods like Matecumbe and Plantation Key. If you’ve got some spare time, add a day trip or tour to your Islamorada vacation itinerary.
Is it worth booking a vacation package to Islamorada?
Whether you want to visit major sights such as Theatre of the Sea and Hurricane Monument on your Islamorada vacation, or coming for its excellent walking trails, views and family-friendly attractions, there’s something for everyone here. With so much to see and do, you’ll soon learn why so many people think Islamorada is a good vacation destination.
How to find the best Islamorada package deals?
Finding a cheap Islamorada package deal is easy with Expedia. After you’ve entered your preferred dates and destination under our “Packages” tab, set your budget, apply a couple of filters and browse what’s available. You can tweak your search by “Amenities,” “Property type,” “Traveller experience” and more. Order the results by “Price: low to high” to discover the most wallet-friendly Islamorada package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Islamorada vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You’ll typically get a better deal than booking each component individually. And you’ll still have the freedom to create a personalized Islamorada vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Islamorada?
If you have your Islamorada vacation dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Islamorada?

  1. Pick your travel dates: What you plan to do in Islamorada and your preferred season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Islamorada.
  3. Work out your trip length: Think about how long you want to spend discovering Islamorada. Plan your days so you can get to all the attractions and experiences you’re interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Islamorada vacation package.

Discover the most popular places to visit in Islamorada

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
Windley Key Fossil Reef Geological State Park

Windley Key Fossil Reef Geological State Park

Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails.

Windley Key Fossil Reef Geological State Park
History of Diving Museum

History of Diving Museum

4/5(1 review)

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

What to do in Islamorada

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

CA $345
per adult
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW

Ft. Lauderdale to Key West Day Trip Quality Day Tours

CA $311
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
Florida Keys Tour and Private Transportation service

Florida Keys Tour and Private Transportation service

CA $1,365
per traveller
Florida Keys Tour and Private Transportation service
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.