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 Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1,143 reviews)
This hotel is not the cleanest, but the location is great and the staff were very friendly and helpful! We tried the restaurant that serves breakfast for the hotel for dinner the night before and it was terrible. No flavor to the food and the drinks were below average. We found other restaurants near by that were delicious. If the rooms were really cleaned it would be a wonderful place to stay.

Reviewed on Apr. 10, 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
Jun. 1 - Jun. 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (1 review)
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 28 - Jul. 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.6/10 Excellent! (57 reviews)
We liked that everything was in walking distance from our villa. The cleanliness of resort and friendliness of the staff was great. What we didn’t like was that a freezer was never fixed properly and the queen bed was terribly uncomfortable. The tv in the second bedroom we were never able to get to work due to not being able to access the proper channel. The hot water ran out in the shower after one shower which was a downfall when you have more than one person to get ready. Overall very nice resort, just a few things that would have worked better for our family.

Reviewed on Mar. 4, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 28 - Jul. 5
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
Beautiful property, restaurants close too early for later eaters.

Reviewed on Apr. 8, 2025

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
Jun. 20 - Jun. 24
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,010 reviews)
Met my needs for relaxation and beautiful ocean views

Reviewed on Apr. 13, 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

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.

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 $276 per night from Apr. 28 to Apr. 29
CA $276
CA $389 total
includes taxes & fees
Apr 28 - Apr 29
9/10 Wonderful! (1,426 reviews)
Nice Resort for the Money
"I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but ..."

Reviewed on Apr. 14, 2025

Chesapeake Beach Resort
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 $376 per night from May 12 to May 13
CA $376
CA $515 total
includes taxes & fees
May 12 - May 13
8.8/10 Excellent! (12 reviews)
"Our stay here was great for the most part! 2 hicupps; the room we were assigned, the shower door leaked all over the floor! However, when letting the fromt desk know, they upgradedus to a room right off the beach ground floor so we were very happy!"

Reviewed on Apr. 12, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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 $310 per night from May 13 to May 14
CA $310
CA $443 total
includes taxes & fees
May 13 - May 14
9/10 Wonderful! (1,063 reviews)
"."

Reviewed on Apr. 12, 2025

Cheeca Lodge & Spa
See all 2,192 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 snap up a vacation package to this destination from CA $612 on Expedia. However, how much your vacation 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 vacation packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We’d recommend booking an Islamorada vacation 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 neighborhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a vacation 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 Theater of the Sea and Hurricane Monument, or take the path less traveled, there’s plenty to see and do on your Islamorada vacation.
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 vacation package well in advance.
Is it cheaper to book an Islamorada vacation as a package?
You can enjoy significant savings on your Islamorada escape by booking a customized vacation 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 vacation 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 accommodations: After you’ve nailed down your travel dates and duration, lock in the right Islamorada vacation package for you.

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 $358
per adult
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
Golden Glare Fishing Charter with Experienced Captain

Golden Glare Fishing Charter with Experienced Captain

CA $935
per traveller
Golden Glare Fishing Charter with Experienced Captain
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 $324
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
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.