How much does an Islamorada vacation package cost?

You can pick up a vacation package to this top destination from CA $836 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?

Pick your travel dates: What you plan to do in Islamorada and your preferred season will help you decide when to go. 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. 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. 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.

Islamorada Vacation Packages & Trips 2025 from $312

Name: Chesapeake Beach Resort
Price range: CA $185
Rating: 9

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.

Park Central South Beach

South Beach

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Miami (MIA)

8.2/10 Very Good! (911 reviews)

Was just a great place to vist. Would recomemd to anyone that has not been to Miami.

Reviewed on Aug. 13, 2025

Pelican Grand Beach Resort - A Noble House Resort

East Fort Lauderdale

per person

Oct 15 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

8.8/10 Excellent! (1,156 reviews)

need microwave in room

Reviewed on Aug. 14, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

per person

Oct 16 - Oct 19

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Miami (MIA)

8/10 Very Good! (1 review)

B Ocean Resort Fort Lauderdale Beach

East Fort Lauderdale

per person

Oct 15 - Oct 22

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Miami (MIA)

7.6/10 Good! (3,019 reviews)

Everything was good

Reviewed on Aug. 14, 2025

EAST Miami Residences

Downtown Miami

per person

Oct 18 - Oct 23

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Miami (MIA)

9/10 Wonderful! (70 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

Things to do in and around Islamorada

Islamorada, Florida, is an ideal destination for families seeking outdoor and beach vacations. Visitors can enjoy a range of activities, including boat tours, oceanfront weekends, and adventure tours. The area boasts excellent beach access and several fishing resorts, along with vibrant shopping areas and malls for a complete getaway experience. With its beautiful surroundings, Islamorada promises memorable experiences for everyone.

Shopping

Rain Barrel Village, a famous shop in Islamorada, offers a charming blend of local art and unique souvenirs. If you're up for a drive, consider visiting the nearby outlets for a wider selection of gifts and bargains to take back home.

Recreation

At Jacob's Aquatic Center, enjoy family-friendly aquatic activities, including swimming and water games. The vibrant atmosphere provides a perfect setting for relaxation and fun. Engage in rejuvenating water exercises or simply unwind by the poolside, soaking up the sun and good vibes in the beautiful Florida Keys.

Adventure

The Florida Keys Dive Center, located 12.9km from Islamorada, offers exhilarating underwater sports experiences amidst vibrant marine life. For a thrilling day, visit Keys Cable Park, situated 35.4km away, where you can enjoy wakeboarding and cable sports. Lastly, Mahogany Hammock, 48.3km away, provides scenic hiking trails through lush landscapes.

Nightlife

Islamorada's nightlife boasts vibrant venues like Jimmy Johnson's Big Chill, just 27.4km away, offering a romantic atmosphere with great drinks. Another option is the Caribbean Club Bar, located 33.8km from town, where you can enjoy lively entertainment and a laid-back vibe perfect for a fun night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Islamorada

Islamorada, Florida, is perfect for families seeking outdoor beach vacations. Explore a variety of attractions, including marinas, beaches, and national parks, which offer unique cultural and adventurous experiences. Don’t miss the local gems like Islamorada County Park and the picturesque Florida Keys. There’s something for everyone, ensuring a memorable getaway for all types of travellers.

Anne's Beach: Enjoy the tranquil beauty of Anne's Beach, where you can relax on soft sands and soak up the sun. This picturesque spot boasts shallow waters perfect for wading and is surrounded by lush tropical vegetation, creating a serene environment ideal for unwinding or picnicking.
Bud n' Mary's Dive Center: Dive into adventure at Bud n' Mary's Dive Center, a hub for outdoor enthusiasts. With its expert guides, you can explore vibrant coral reefs, encounter diverse marine life, and experience the thrill of water sports, making it a must-visit for adventure seekers.
Islamorada County Park: Ideal for families, Islamorada County Park offers a blend of recreational activities and natural beauty. With playgrounds, picnic areas, and walking trails, it’s a great spot for outdoor fun and relaxation amidst the vibrant city atmosphere.

Best time to go to Islamorada

The best time to visit Islamorada can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Islamorada falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Islamorada falls in January, visitor numbers are average and weather is mostly sunny with no rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.0°F (21.1°C)	No Rain	Mostly Sunny	Average	Average
February	71.8°F (22.1°C)	No Rain	Mostly Sunny	Average	Slightly High
March	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
April	76.6°F (24.8°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
July	83.8°F (28.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Average
September	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately Low	Average

Tips to save on your trip to Islamorada

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically September to November) for more affordable package holidays to Islamorada.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

CA $185

CA $286 total

Sep 14 - Sep 15

includes taxes & fees

9/10 Wonderful! (1,497 reviews)

"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"

Reviewed on Aug. 11, 2025

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Fully refundableReserve now, pay when you stay

CA $212

CA $332 total

Aug 20 - Aug 21

includes taxes & fees

9/10 Wonderful! (1,142 reviews)

"The room we booked in the lodge with the balcony overlooking the golf course was absolutely incredible and felt private. The food quality in the hotel, however, was not very good, especially for the price"

Reviewed on Aug. 12, 2025

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Fully refundableReserve now, pay when you stay

CA $231

CA $351 total

Sep 1 - Sep 2

includes taxes & fees

8.8/10 Excellent! (1,240 reviews)

"Top notch all around."

Reviewed on Aug. 13, 2025

See all 2,184 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.