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.
Luxuri Suites

Luxuri Suites

South Beach
Save 100% on your flight
CA $465
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
6.6/10 (58 reviews)
Do not book here

Reviewed on Aug 28, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $15,819
per person
Nov 21 - Nov 27
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Miami Vacation Rentals - Brickell

Miami Vacation Rentals - Brickell

Brickell
Save 100% on your flight
CA $2,152
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (570 reviews)
Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

Downtown Miami
Save 100% on your flight
CA $1,929
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (92 reviews)
Fantastic view! Easily the best part about this listing. The view of the water was incredible! Great space, very clean, and easily walkable to lots of great spaces. Also using the facilities of the Hotel were wonderful as well.

Reviewed on Oct 1, 2026

EAST Miami Residences

EAST Miami Residences

Brickell
Save 100% on your flight
CA $3,191
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (151 reviews)
beatiful place

Reviewed on Sep 30, 2026

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
A pier extending into calm waters with a covered seating area and a sandy beach.

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 Robbie’s of Islamorada are top sights worth seeing.

A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores might not have many top sights, but Rain Barrel Village and Founders Park are two attractions nearby that you can check out.

A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Sunset Drive Beach.

A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.

Things to do in and around Islamorada

Islamorada, Florida, is perfect for family beach vacations and outdoor adventures. Enjoy a variety of activities, including boat tours, oceanfront weekends, and thrilling adventure tours. With ample beach access and renowned fishing resorts, there's something for everyone. Don't forget to explore the local shopping mall and vibrant shopping areas for a complete experience.

Shopping

In Islamorada, visit Rain Barrel Village for unique gifts and souvenirs, featuring local art and crafts in a vibrant atmosphere. If you're up for a drive, head to the nearby Founders Park Marketplace, offering a variety of shops and dining options to enhance your shopping experience.

Recreation

Jacob's Aquatic Center is a family-friendly venue located 27.4km from Islamorada, offering a refreshing aquatic experience. Enjoy swimming, water aerobics, and relaxation by the pool, making it an ideal spot for rejuvenation while soaking up the Florida sun.

Adventure

Experience the thrill of scuba diving at Florida Keys Dive Center, located 12.9km from Islamorada, where you can explore vibrant underwater ecosystems. For an adrenaline rush, visit Keys Cable Park, 35.4km away, offering wakeboarding and water sports. Hike the scenic Pa-hay-okee Trail, 38.6km from Islamorada, for stunning views.

Nightlife

Experience the vibrant nightlife in Islamorada at Jimmy Johnson's Big Chill, a lively pub 27.4km away, offering entertainment and romantic vibes. Alternatively, enjoy the Caribbean Club Bar, located 33.8km away, where you can soak in the lively atmosphere and enjoy a drink with a view.

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

Find the best attractions in Islamorada

Islamorada is perfect for family-friendly beach vacations, offering a range of outdoor activities and cultural experiences. Explore local attractions such as marinas, beaches, and state parks, while the Islamorada County Park provides additional fun for all ages. Don’t miss the chance to discover the unique charm of the Florida Keys, ensuring your visit is filled with unforgettable moments and beautiful scenery.

  • Anne's Beach: Experience the serene beauty of Anne's Beach, where you can relax on soft sands and enjoy the tranquil beach vibes. Ideal for sunbathing and swimming, this spot offers a perfect escape to unwind and soak up the Florida sun.
  • Windley Key Fossil Reef Geological State Park: Discover the adventure and stunning scenery at Windley Key Fossil Reef Geological State Park. Explore nature trails and learn about the fascinating geological history of the area, all while enjoying the great outdoors.
  • History of Diving Museum: Immerse yourself in the rich culture of diving at the History of Diving Museum. This unique museum showcases the evolution of diving equipment and provides insights into underwater exploration, making it a must-visit for history buffs.

Best time to go to Islamorada

The best time to visit Islamorada is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.0°F (21.1°C)No RainMostly SunnyAverageAverage
February71.8°F (22.1°C)No RainMostly SunnyAverageSlightly High
March72.9°F (22.7°C)No RainMostly SunnyModerately HighSlightly High
April76.6°F (24.8°C)No RainMostly SunnyModerately HighSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageAverage
July83.8°F (28.8°C)Light RainMostly SunnyModerately HighAverage
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowSlightly Low
December72.9°F (22.7°C)No RainMostly SunnyModerately LowAverage

Tips to save on your trip to Islamorada

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Islamorada.
  • 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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
CA $184
CA $311 total
Oct 2 - Oct 3
includes taxes & fees
9.2/10 Wonderful! (1,475 reviews)
"The room was a little loud from the A/C unit but great stay"

Reviewed on Sep 30, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $197
CA $302 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,786 reviews)
"Great place"

Reviewed on Sep 30, 2026

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
CA $306
CA $449 total
Oct 18 - Oct 19
includes taxes & fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
See all 2,116 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.

Stay near popular Islamorada attractions

A beach with a wooden structure, clear blue sky, and dense green foliage.

Anne's Beach

7.8/10 (597 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.
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A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.
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A white tower with a dome, surrounded by palm trees and greenery.

Founders Park

8.8/10 (450 reviews)
Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.
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Robbie’s of Islamorada

8.4/10 (15 reviews)
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
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Islamorada County Park

8.8/10 (198 reviews)
Enjoy the beautiful sunsets and explore Islamorada County Park, a lovely green space in Islamorada. Discover the seafood restaurants and entertainment choices in this family-friendly area.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.
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Sunset Drive Beach

9.0/10 (91 reviews)
Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?
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What to do in Islamorada

Islamorada Sunset Cruise with Champagne Toast and Snacks

Islamorada Sunset Cruise with Champagne Toast and Snacks

CA $94
per adult
80% of travellers recommend
Islamorada Sunset Cruise with Champagne Toast and Snacks
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

CA $96
per adult
100% of travellers recommend
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
Snorkel and Sandbar Combo Adventure in Islamorada

Snorkel and Sandbar Combo Adventure in Islamorada

CA $156
per adult
Snorkel and Sandbar Combo Adventure in Islamorada
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 $465 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.

Explore a world of travel with Expedia

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