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 beach holidays, offering a variety of activities such as kayaking, swimming, and other aquatic adventures. Visitors can enjoy the local resorts and explore shopping areas and mall centres. With numerous outdoor options, Islamorada provides a perfect blend of relaxation and excitement for all ages.

Shopping

Discover Rain Barrel Village, a charming shopping spot in Islamorada with a lively atmosphere, offering unique gifts and local art. If you're up for a drive, visit the nearby shops in Key Largo, located around 16.1km away, for more diverse shopping options and delightful souvenirs.

Recreation

Explore Jacob's Aquatic Center, located 27.4km from Islamorada, where you can enjoy family-friendly activities in a vibrant aquatic setting. Swim, relax by the pool, or partake in various water-based exercises to rejuvenate your body and mind amidst a welcoming atmosphere.

Adventure

The Florida Keys Dive Center offers thrilling underwater sports, located 12.9km from Islamorada, perfect for diving enthusiasts seeking adventure beneath the waves. For a different thrill, visit Keys Cable Park, 35.4km away, where you can enjoy exciting water sports in a vibrant setting. Lastly, explore the scenic Pa-hay-okee Trail, 38.6km from Islamorada, for a delightful hiking experience amidst stunning outdoor views.

Nightlife

The nightlife in Islamorada offers a charming blend of romance and entertainment. Enjoy a drink at Jimmy Johnson's Big Chill, located 27.4km away, or relax at the Caribbean Club Bar, 33.8km from the centre, both providing a vibrant atmosphere perfect for a memorable evening.

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

Find the best attractions in Islamorada

Islamorada offers a delightful vacation experience for families and outdoor enthusiasts alike, boasting popular attractions such as marinas, stunning beaches, and national parks. Visitors can immerse themselves in a variety of activities that highlight the area's natural beauty, cultural heritage, and beachside relaxation. Whether you seek adventure or leisure, Islamorada caters to all, ensuring a memorable getaway in this picturesque Florida destination.

  • Anne's Beach: Experience the quintessential beach vibes at Anne's Beach, where soft sands and gentle waves create a serene atmosphere. It's an ideal spot for sunbathing, picnicking, and enjoying stunning sunsets over the horizon.
  • Bud n' Mary's Dive Center: Dive into adventure at Bud n' Mary's Dive Center, a vibrant marina offering thrilling outdoor experiences. Whether you’re into scuba diving or fishing, the centre provides access to the beautiful waters of the Florida Keys, perfect for exploring colourful marine life.
  • Islamorada County Park: Enjoy a family-friendly outing at Islamorada County Park, where lush greenery and recreational facilities await. This urban park is perfect for leisurely strolls, picnics, or engaging in various sports activities amidst a lively city atmosphere.

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

Booking tips and Expedia advantages for Islamorada

Islamorada provides several cost-saving opportunities for travellers. You can enjoy free access to beautiful spots like Anne's Beach and Islamorada County Park. For transportation, consider biking or walking, as the area is pedestrian-friendly. The best time to visit is from September to November when accommodation prices are lower; avoid the peak season from February to April. Booking your hotel a month in advance and opting for Tuesday stays can also help you save. Utilise Expedia's package deals to combine flights and hotels for additional savings.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Islamorada are September to November, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher.
  • The best time to book a hotel: Book your hotel in Islamorada about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Islamorada is Tuesday. The most expensive day to stay in Islamorada is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To uncover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Islamorada with your flights and activities through an Expedia package.

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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is Rp3.309.569 per night from 20 Nov to 21 Nov
Rp3.309.569
Rp4.845.941 total
20 Nov - 21 Nov
includes taxes & fees
9/10 Wonderful! (1,258 reviews)
A few problems with the room, ex. Coffee maker, sink in bathroom, shower, but over all excelent

Reviewed on 27 Oct 2025

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 Rp2.038.129 per night from 3 Nov to 4 Nov
Rp2.038.129
Rp3.228.389 total
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (1,548 reviews)
I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again.

Reviewed on 27 Oct 2025

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 Rp2.570.737 per night from 30 Nov to 1 Dec
Rp2.570.737
Rp3.996.045 total
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (1,270 reviews)
We enjoyed our stay a beautiful place, but there was no free breakfast

Reviewed on 24 Oct 2025

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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.