Islamorada Holidays

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Top Flight + Hotel Deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
Kompose Boutique Hotel Miami Airport
W South Beach
1 Hotel South Beach
Hollywood Beachside Boutique Suites
The Shelborne By Proper, a Member of Design Hotels

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 €371 per night from 22 Mar to 23 Mar
€371
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (1,655 reviews)
Just perfect

Reviewed on 12 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 €421 per night from 22 Feb to 23 Feb
€421
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (1,300 reviews)
View and ambience

Reviewed on 12 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 €413 per night from 25 Feb to 26 Feb
€413
25 Feb - 26 Feb
includes taxes & fees
8.8/10 Excellent! (1,250 reviews)
The clean room, the ambience and the amenities are perfect 👌

Reviewed on 12 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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