Deals on vacations and trips to Islamorada

Save when you book Islamorada package deals

Choose two or more items and save on your trip:

Islamorada flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Banana Bay Resort & Marina
1 Hotel South Beach
Henrosa Hotel
Cavalier Hotel South Beach
Isle of Venice

Top Islamorada hotels deals

Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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.

Popular places to visit

Top reasons for your vacation to Islamorada

  • Breathtaking Sunsets: Islamorada is known for its stunning sunsets over the ocean, providing a picturesque backdrop for your vacation.
  • Outdoor Activities: With its close proximity to the sea, Islamorada offers a wide range of outdoor activities including fishing, snorkeling, and diving, making it a perfect destination for adventure seekers.
  • Delicious Seafood: Indulge in mouthwatering seafood at the many top-notch restaurants in town, where you can enjoy fresh catches of the day.
  • Vibrant Entertainment Scene: Experience the lively entertainment scene in Islamorada, with options ranging from visiting the theater to enjoying opera performances.
  • Treasure Harbor and Mangrove Trees: Explore the treasure harbor and admire the stunning mangrove trees, which add to the natural beauty of Islamorada.

Explore the best activities and sights in Islamorada

Islamorada, located in the Florida Keys, is a perfect outdoor vacation destination for families. With its close proximity to the sea, there are plenty of activities to engage in, such as fishing, snorkeling, and diving. You can also relax on the beautiful beaches and enjoy breathtaking sunsets. For entertainment, there are options like visiting the theater or enjoying opera performances. Don't forget to indulge in delicious seafood at the best places in town. Explore the treasure harbor and admire the stunning mangrove trees. In Islamorada, there are endless outdoor activities to keep the whole family entertained!

  1. Bud n' Mary's Dive Center: This marina Point of Interest offers a mesmerizing experience with its crystal-clear sea, pristine beaches, and picturesque sunsets. It is a paradise for fishing enthusiasts, with abundant opportunities to catch a variety of fish. Families can enjoy the family-friendly atmosphere while exploring the wonders of nature and indulging in delicious seafood. The relaxing ambiance and breathtaking scenery make it an ideal spot to unwind and soak in the beauty of the marina.
  2. Founders Park: Located by the sea, Founders Park is a marina Point of Interest that showcases stunning sunsets, sandy beaches, and a tranquil atmosphere. Nature lovers can immerse themselves in the beauty of the surroundings and engage in fishing activities. Families can enjoy entertainment options such as opera and theater, while seafood lovers can savor delectable dishes. Founders Park provides an outdoor adventure experience, allowing visitors to indulge in beach activities and bask in the natural wonders of the sea.
  3. Theater of the Sea: As an aquarium Point of Interest, Theater of the Sea offers an unforgettable family experience. Dive into the world of sea creatures, enjoy captivating operas and theater performances, and witness mesmerizing sunsets by the sea. Nature enthusiasts can appreciate the beauty of dolphins while fishing enthusiasts can engage in their favorite activity. With its diverse range of attractions, Theater of the Sea guarantees entertainment and a deep connection with marine life.

Where to stay in Islamorada

Get ready for an unforgettable outdoor vacation in Islamorada, Florida! With its beautiful beaches and stunning ocean views, this lush oasis is truly a place in paradise. Whether you're a fishing enthusiast, a snorkeling lover, or simply seeking relaxation, Islamorada has it all. Immerse yourself in the vibrant entertainment scene, enjoy a breathtaking sunset, or indulge in delicious seafood. And if you're up for an adventure, don't miss the opportunity to take a trip to nearby Key West. Get ready to create lasting memories with your family in this outdoor haven.

  1. Matecumbe: Matecumbe is a popular neighborhood in Islamorada known for its charming atmosphere and local affinities. Families can enjoy strolling through the neighborhood's quaint streets, browsing unique shops, and dining at local restaurants. With its beautiful beaches, Matecumbe also offers opportunities for outdoor activities like swimming and sunbathing. The neighborhood's laid-back vibe and friendly locals create a welcoming environment for families looking to relax and unwind.
  2. Venetian Shores: Venetian Shores is another popular neighborhood in Islamorada that offers a unique experience for outdoor vacation with your family. Known for its picturesque canals and waterfront properties, Venetian Shores is a paradise for boating and fishing enthusiasts. Families can rent a boat and explore the crystal-clear waters, go fishing for local catch, or simply enjoy the stunning views. The neighborhood's serene atmosphere and close proximity to nature make it an ideal destination for families seeking outdoor adventures.
  3. Lower Matecumbe Beach: Lower Matecumbe Beach is a must-visit neighborhood in Islamorada, offering a wide range of outdoor activities for families. From fishing and diving to snorkeling and sunset watching, this neighborhood is a paradise for water lovers. Families can relax on the sandy beaches, explore the vibrant marine life, or enjoy thrilling water sports. In addition, Lower Matecumbe Beach also offers entertainment options like theaters and operas, ensuring a well-rounded experience for the whole family. Don't miss out on the delicious seafood options available in the neighborhood as well.

Best times to go to Islamorada

The travel seasons of Islamorada

Trips to Islamorada show a small change in popularity throughout the year. The peak season to visit is from February to April, with March being the highest month. Off-peak season starts from October to December, and October sees the least travelers.

Islamorada has something in store for you whenever you visit. January is the coldest month of the year, while August is hottest, with average temperatures up to 84.4 degrees Fahrenheit. The wettest month in Islamorada is September, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January70.0°F (21.1°C)No Rain (Dry)Mostly Sunny
February71.8°F (22.1°C)No Rain (Dry)Mostly Sunny
March72.9°F (22.7°C)No Rain (Dry)Mostly Sunny
April76.6°F (24.8°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.4°F (28.0°C)Light RainMostly Sunny
July83.8°F (28.8°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.3°F (28.5°C)Light RainMostly Sunny
October80.2°F (26.8°C)Light RainMostly Sunny
November75.9°F (24.4°C)Light RainMostly Sunny
December72.9°F (22.7°C)No Rain (Dry)Mostly Sunny

Food and dining in Islamorada

When visiting Islamorada, Florida, be prepared to indulge in the delectable local cuisine. With its idyllic views of Islamorada and poolside fare, Lazy Days Restaurant is a highly rated and popular choice. For a taste of North American cuisine, head to Wahoo's Bar & Grill, which also offers breathtaking views of the shores of Islamorada. If you're in the mood for pizza, Whale Harbor Restaurant Marina is a highly rated spot that will transport you to a world of sun and delicious food. Don't miss out on these culinary gems on the southside of Islamorada Key.

How do I find my perfect vacation package with Travelocity?

Ensure the entire crew experiences an abundance of enjoyment on your upcoming journey. Utilize our user-friendly filters to find an ideal vacation package tailored to your family's needs. Discover destinations appropriate for your children's age ranges, coupled with accommodations offering additional amenities. Making the right selection will not only save you money but also mitigate any potential temper tantrums.

Why should I book with Travelocity?

Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family book with us, so you can spend less time worrying and more time creating cherished memories. We are committed to helping you find and plan your ideal trip, with transparent pricing, verified reviews, and round-the-clock customer support before, during, and after your vacation.

How can I save money on my trip to Islamorada?

Save money by visiting Islamorada during the off-peak season from October to December. Bundle your flight, hotel, and car bookings to get a discounted price. While in Islamorada, you can enjoy inexpensive local activities such as fishing, snorkeling, and watching beautiful sunsets. These affinities offer great entertainment for the whole family without breaking the bank. Don't miss the chance to indulge in affordable seafood dishes and experience the local theater scene as well. Islamorada has something for everyone at a budget-friendly cost!

Frequently asked questions

How much are vacation packages to Islamorada?
With vacation packages available from just $425, you won’t need to blow out the credit card for your getaway to Islamorada. Travelocity is here to help. Bundle flights, hotels and experiences into a convenient package and score some impressive discounts. The more you book, the greater the savings.
How long should my Islamorada vacation be?
Around 3 nights is what many visitors book for their Islamorada vacation. That’s a good starting point, but there’s so much more to explore if you give yourself a couple of extra days.
Where can I get the best vacation package deals for Islamorada?
You can snap up amazing Islamorada package deals with Travelocity. Pick and choose from 400 airlines and 1,000,000 worldwide properties and turn those vacation dreams into reality.
Why should I book my Islamorada vacation bundle with Travelocity?
Whether you’re planning a month-long vacation or a last-minute weekend trip, we have plenty of exciting destinations to choose from at a good price. And on top of that, we provide 24/7 assistance, high-quality service and a Price Match Guarantee. Save yourself time and money and book your dream vacation today.
Will I save money on my Islamorada car rental if I book it with a hotel or flight?
With an Islamorada vacation package, you can bundle your hotel, car and flight bookings and save loads. If you can’t wait to explore the best of this fabulous city, why not make a beeline for PortMiami? This top sight is 65 mi from Islamorada. With your own rental car, you’ll be there belong long.
What is the best time of year to go to Islamorada?
November, December and January are the months when most travelers visit, while April, September and October are usually quieter. If you’re traveling with a limited budget, consider visiting during . is usually regarded as the most expensive time of the year to stay here.
What is there to do in Islamorada?
While venturing off the beaten track is no doubt rewarding, you shouldn’t ignore the well-known sights that make a place famous. Theater of the Sea and Bud n Marys Dive Center are a couple of them in Islamorada.
Where should I stay when visiting Islamorada?
If you’re after someplace comfortable to spend your nights, have a look at the Postcard Inn Beach Resort & Marina. It’s the top pick for many travelers.

Photos of local treasures

Browse Islamorada vacation photos for more inspiration

Islamorada featuring a beach and tropical scenes