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.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Lazy river was great along with the pool and great beach access. GG the lady server that brings you food and drinks at the pool was one of the nicest and kindest people I’ve ever met at a hotel. She truly deserves a big raise. If GG isn’t making a little less than the manager then the management doesn’t know how to manage. GG literally went out of her way to try to make your pool day unforgettable. The only place I would ever be staying at when I return to Fort Lauderdale would be Pelican and reason being is the staff.

Reviewed on Jul. 12, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 17 - Sep 23
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Save 100% on your flight
per person
Oct 1 - Oct 8
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
9/10 Wonderful! (128 reviews)
i like the the hotel is apartments style with a full kitchen,washer and dryer.

Reviewed on Jul. 10, 2025

Pier Sixty-Six

Pier Sixty-Six

5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 17 - Sep 23
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.4/10 Exceptional! (76 reviews)
Stellar customer service.

Reviewed on Jul. 8, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Save 100% on your flight
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (63 reviews)
No me gustó el sector ya que hay mucho ruido en la calle motos carros acelerando No deja dormir La habitación me gustó bastante pero no logré Disfrutarla

Reviewed on May 23, 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

Islamorada Beach Vacation

Relax along the shoreline and feel the wind through your hair during your Islamorada vacation. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometres from the town centre. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.

Things You Should Know About Islamorada

  • Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
  • If you're searching for lots of room to spread out and relax, Islamorada private vacation homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour and Bud N' Mary's Fishing Marina will fit the bill.
  • Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.

Ready to book your vacation to Islamorada?

 

Choose your dates

Islamorada Hotel Deals

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 $240 per night from Aug 13 to Aug 14
CA $240
CA $363 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (1,134 reviews)
"We loved the property grounds and attention to detail from the walking paths to the lagoon and the tiki torches. Our favorite time was spent in the evening on the beach as it was so calm and peaceful. We wish the beach was more usable and swimmable however. Even getting the kayaks into the water ..."

Reviewed on Jul. 12, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Aug 12 to Aug 13
CA $202
CA $305 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (1,488 reviews)
"We loved it!"

Reviewed on Jul. 10, 2025

Chesapeake Beach Resort
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Aug 4 to Aug 5
CA $285
CA $413 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Fabulous vacation experience! Beautiful facilites with phenomenal ocean views!!!"

Reviewed on Jul. 10, 2025

Islander Resort
See all 2,178 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

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

Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

CA $204
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

CA $683
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

CA $340
per adult
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
See all activities in Islamorada

Frequently asked questions

How much does an Islamorada vacation package cost?
You can pick up a vacation package to this top destination from CA $761 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.

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