Islamorada Holidays

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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 is an ideal destination for family and outdoor beach vacations, offering a delightful array of activities. Visitors can enjoy a variety of attractions, including resorts, shopping centres, and local markets. Key experiences include sightseeing, fishing getaways, and snorkelling trips, alongside numerous water sports rentals ensuring plenty of fun and adventure for all ages.

Shopping

Visit Rain Barrel Village in Islamorada for a unique shopping experience, featuring local art and crafts. If you're up for a drive, check out the nearby shops in Key Largo, where you can find more souvenirs and gifts in a vibrant atmosphere.

Recreation

Experience rejuvenation at Jacob's Aquatic Center, a family-friendly aquatic venue located 27.4km from Islamorada. Enjoy refreshing swims, engaging water activities, and a serene environment that promotes relaxation and wellness for all ages, making it an ideal retreat for relaxation and fun.

Adventure

Experience the thrill of underwater exploration at Florida Keys Dive Center, located 12.9km from Islamorada, where adventure and sports combine. For a different kind of excitement, visit Keys Cable Park, 35.4km away, offering exhilarating water activities. Finally, immerse yourself in nature along the Pa-hay-okee Trail, 38.6km away, with stunning scenery.

Nightlife

In Islamorada, experience vibrant nightlife at Jimmy Johnson's Big Chill, 27.4km away, where romance and entertainment blend perfectly. Alternatively, visit the Caribbean Club Bar, located 33.8km from the heart of Islamorada, offering a similarly enchanting atmosphere for a delightful evening out.

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

Find the best attractions in Islamorada

Islamorada is a fantastic destination for families seeking outdoor and beach vacations. Explore the stunning marinas, beautiful beaches, and nearby national parks that offer thrilling adventures and relaxation. Don't miss the chance to visit the Florida Keys, enjoy the tranquil Islamorada sandbar, and unwind at Islamorada County Park for a memorable experience in this picturesque locale.

  • Founders Park: This marina offers a perfect blend of adventure and relaxation, featuring beautiful outdoor spaces and beach vibes. You can enjoy various water sports, picnic areas, and scenic views, making it an ideal spot for families and outdoor enthusiasts alike.
  • History of Diving Museum: Immerse yourself in the intriguing culture of diving at this museum, which showcases the evolution of diving equipment and its historical significance. With captivating exhibits and artefacts, it provides a unique insight into underwater exploration.
  • Sunset Drive Beach: A tranquil haven for beach lovers, Sunset Drive Beach boasts stunning sunsets and a laid-back atmosphere. Relax on the sandy shores, swim in the clear waters, or enjoy a leisurely stroll along the coastline.

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.

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

  • 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 Holiday

Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. 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 holiday 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.

Top hotels in Islamorada

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 S$418 per night from 11 Feb to 12 Feb
S$418
11 Feb - 12 Feb
includes taxes & fees
9.2/10 Wonderful! (1,667 reviews)
We loved this place. It’s small and easy to get around. Beautiful setting, watched the sunrise from bed, and the best hotel breakfast we’ve ever had.

Reviewed on 3 Feb, 2026

Chesapeake Beach Resort
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 S$601 per night from 10 Feb to 11 Feb
S$601
10 Feb - 11 Feb
includes taxes & fees
9.2/10 Wonderful! (1,296 reviews)
Paradise away from Home!! Thank you!

Reviewed on 7 Feb, 2026

Cheeca Lodge & Spa
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 S$424 per night from 11 Feb to 12 Feb
S$424
11 Feb - 12 Feb
includes taxes & fees
8.8/10 Excellent! (1,264 reviews)
All good, nice bartender inside downstairs, and easy walk to fish and eat

Reviewed on 5 Feb, 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.

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What to do in Islamorada

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.