Islamorada Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Creekside Inn
Casablanca Miami Beach
The Retreat Collection at 1 Hotel & Homes South Beach
Barcelona Studios Guesthouse
The Key West Hotel

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada

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

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $424 per night from Apr 12 to Apr 13
CA $424
CA $578 total
Apr 12 - Apr 13
includes taxes & fees
9.2/10 Wonderful! (1,298 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on Mar 12, 2026

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 $300 per night from Apr 15 to Apr 16
CA $300
CA $415 total
Apr 15 - Apr 16
includes taxes & fees
9.2/10 Wonderful! (1,667 reviews)
Staff wasn’t very helpful or accommodating.

Reviewed on Mar 15, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is CA $339 per night from Mar 26 to Mar 27
CA $339
CA $482 total
Mar 26 - Mar 27
includes taxes & fees
8.8/10 Excellent! (1,255 reviews)
Desk staff was OK. Bar and restaurant staff seemed slow and overwhelmed even with a small crowd. Cleaning staff wandered around slowly looking at their phones.

Reviewed on Mar 14, 2026

Amara Cay Resort
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.

Discover the most popular places to visit in Islamorada

What to do in Islamorada

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.