Islamorada Holidays

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Top Flight + Hotel Deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
Fort Lauderdale Beach Resort by Vacatia
1 Hotel South Beach
Cavalier Hotel South Beach
Mayfair House Hotel & Garden
President Hotel

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 beach holidays, offering a variety of activities such as resort stays, shopping at local centres, and vibrant shopping areas. Key attractions include scenic sightseeing spots, fishing getaways, and exciting snorkelling trips, alongside numerous water sports rentals to enhance your outdoor experience.

Shopping

Rain Barrel Village is a charming spot in Islamorada, filled with unique gifts and local artwork, capturing the area's vibrant spirit. If you're up for a drive, consider visiting the nearby outlets in Key Largo for a wider variety of shops and discounts.

Recreation

At Jacob's Aquatic Center, located 27.4km from Islamorada, families can enjoy a variety of water activities in a welcoming atmosphere. This aquatic venue offers swimming, fitness classes, and relaxation opportunities, making it an ideal spot for wellness and recreation amidst the beautiful Florida Keys.

Adventure

At Florida Keys Dive Center, located 12.9km from Islamorada, immerse yourself in the vibrant underwater world, perfect for diving enthusiasts. Alternatively, experience the thrill of wakeboarding at Keys Cable Park, situated 35.4km away, or hike the scenic Pa-hay-okee Trail, 38.6km from town, for breathtaking views.

Nightlife

Islamorada's nightlife offers a vibrant atmosphere with romantic vibes. Enjoy a refreshing drink at Jimmy Johnson's Big Chill, located 27.4km away, or head to the Caribbean Club Bar, 33.8km away, for lively entertainment and a warm Caribbean flair.

*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 families seeking outdoor and beach vacations, with attractions like marinas, beaches, and national parks. Visitors can enjoy the famous Islamorada Sandbar and explore the scenic Florida Keys, while the Islamorada County Park offers additional recreational opportunities. Whether you're after adventure or relaxation, this charming locale caters to all types of travellers looking to make the most of their time in the sun.

  • Bud n' Mary's Dive Center: This vibrant marina offers an exhilarating atmosphere for adventure seekers. With diving and fishing excursions, it’s perfect for those eager to explore the stunning underwater world, teeming with colourful marine life and vibrant coral reefs.
  • Sunset Drive Beach: Renowned for its idyllic beach vibes, Sunset Drive Beach invites you to unwind on soft sands while soaking in breathtaking sunsets. It’s an ideal spot for relaxation, swimming, or simply enjoying the tranquil ocean views.
  • Islamorada County Park: This urban park caters to families with its spacious green areas and outdoor activities. Perfect for a picnic or a leisurely stroll, it provides a delightful escape within the city, blending nature with recreational fun.

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

  • 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 to Islamorada during the low season (September to November) for more affordable options.
  • 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 €240 per night from 9 Jun to 10 Jun
€240
9 Jun - 10 Jun
includes taxes & fees
9.2/10 Wonderful! (1,730 reviews)
"Check in was so professional and friendly. Room was very clean. Staff very helpful! Great stay!"

Reviewed on 18 May 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 €326 per night from 7 Jun to 8 Jun
€326
7 Jun - 8 Jun
includes taxes & fees
9.2/10 Wonderful! (1,316 reviews)
"We really enjoyed our stay at Checca Lodge. Our room was wonderful and the staff was very friendly. Great place to unwind, live music was nice in the evenings. The pier is a great addition and we enjoyed fishing from the pier."

Reviewed on 18 May 2026

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is €261 per night from 31 May to 1 Jun
€261
31 May - 1 Jun
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"Was not worth the 1200 per night we spent!"

Reviewed on 19 May 2026

Islander 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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