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A beach with white lounge chairs, a covered pavilion, and palm trees.

Islamorada Vacation Packages

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The Latest Islamorada Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • On the beach, sun loungers, beach towels
    Oct 11 - Oct 17

    Pelican Hotel + Flight

    South Beach
    6 nights
    4.0 star property
    9.2/10 - Wonderful (491 reviews)
    "An incredibly cozy place with a great location and clean facilities; plus, the service from the entire team is exceptionally friendly and respectful."
    Reviewed August 1, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $1,646
    CA $937
    per traveller
    found 1 day ago
    Pelican Hotel
  • Family Studio, 2 Double Beds, Non Smoking, Partial Sea View | View from room
    Oct 11 - Oct 17

    Casablanca Miami Beach + Flight

    North Beach
    6 nights
    3.0 star property
    5.8/10 - (327 reviews)
    "Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No..."
    Reviewed July 23, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $19,631
    CA $8,145
    per traveller
    found 1 day ago
    Casablanca Miami Beach
  • 3 outdoor pools
    Oct 11 - Oct 17

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    6 nights
    5.0 star property
    8.0/10 - 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 June 22, 2016
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $27,830
    CA $13,214
    per traveller
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Oct 11 - Oct 17

    1 Hotel South Beach + Flight

    South Beach
    6 nights
    5.0 star property
    9.4/10 - Exceptional (1,586 reviews)
    "Everything was Amazing!"
    Reviewed August 2, 2026
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $4,468
    CA $2,594
    per traveller
    found 1 day ago
    1 Hotel South Beach
  • 4 outdoor pools, sun loungers
    Oct 11 - Oct 17

    Nobu Hotel Miami Beach + Flight

    Mid Beach
    6 nights
    5.0 star property
    8.6/10 - Excellent (1,444 reviews)
    Roundtrip • Hamilton (YHM) - Miami (MIA)
    YHM - MIA • 1 stop MIA - YHM • 1 stop
    CA $2,604
    CA $1,516
    per traveller
    found 1 day ago
    Nobu Hotel Miami Beach

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Learn more about Islamorada
A beachside café with colorful chairs and tables, palm trees, and a view of the ocean.

Matecumbe

Matecumbe captures the essence of the Florida Keys with its laid-back charm and coastal beauty. Anne's Beach and Sunset Drive Beach offer pristine shorelines perfect for relaxing or swimming. Visitors can explore marine life at Bud n' Mary's Dive Centre or feed tarpon at Robbie's of Islamorada. This resort community balances tourism with authentic Keys lifestyle. Florida Keys Brewing Co. provides local craft beers after a day of snorkelling crystal-clear waters. The Hurricane Monument and MoradaWay Arts District showcase the area's rich history and creative spirit. Waterfront paths offer stunning views of both Atlantic Ocean and Florida Bay.
A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Lower Matecumbe Beach offers a serene Florida Keys escape where powder-soft sand meets crystal-clear turquoise waters. The pristine Atlantic shoreline invites visitors to unwind while scenic overlooks provide spectacular coastal vistas. Sunset Drive Beach and Anne's Beach showcase the area's natural beauty. This tranquil area balances tourism with authentic Keys living. Waterfront seafood restaurants serve fresh catches while boutique shops sell tropical souvenirs. Luxury resorts and intimate bed-and-breakfasts provide comfortable bases for exploring nearby mangrove preserves by kayak or snorkelling the calm, shallow waters.
A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores in Islamorada offers a luxurious waterfront escape with direct access to the Atlantic Ocean and Florida Bay. Private canal-front properties feature personal docks where you can launch your boat for a day of fishing or island exploration. This upscale residential area provides the perfect base for travellers seeking exclusive waterfront vacation rentals. The peaceful area streets lead to high-end homes with private pools and tropical landscaping. Though lacking shops or restaurants within its boundaries, Venetian Shores sits just minutes from Founders Park and local attractions like the History of Diving Museum. Water activities dominate the experience in this serene Keys community.
A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

This affordable Keys hideaway puts you right on the beautiful shores of Islamorada. Seabreeze Trailer Park offers a laid-back alternative to pricey resorts while still delivering stunning ocean views. Fish, swim, or snorkel just steps from your door. The nearby Founders Park and Florida Keys Dive Centre provide plenty of outdoor recreation options. Windley Key Fossil Reef Geological State Park offers fascinating natural history just a short drive away. Palm-lined paths and gentle waves create the perfect backdrop for authentic Florida Keys living.

Discover the most popular places to visit in Islamorada

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 family-friendly area.

What to do in Islamorada

Islamorada Sunset Cruise with Champagne Toast and Snacks

Islamorada Sunset Cruise with Champagne Toast and Snacks

CA $100
per adult
80% of travellers recommend
Islamorada Sunset Cruise with Champagne Toast and Snacks
See all activities in Islamorada

Islamorada Hotel Deals

Balcony

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
1 km from Islamorada
9.2 out of 10, Wonderful, (1,357 reviews)
The price is CA $206
CA $334 total
includes taxes & fees
Aug 18 - Aug 19
Cheeca Lodge & Spa
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.
See all properties 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 $937 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.

Book with confidence

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.

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.

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.