Islamorada Holidays from £1,102

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Your Islamorada Holiday

The laid-back lifestyle and spectacular views are just the beginning of the things Islamorada has to offer. Enjoy the sights and sounds of this captivating city the way you want with a customised Islamorada holiday package. You'll want to do some exploring during your trip to Islamorada. Make time for popular attractions like Theatre of the Sea, Bud n Marys Dive Centre and Founders Park. Check out Expedia's wide range of travel options and start organising your dream holiday to Islamorada today.

Top Islamorada Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
The Retreat Collection at 1 Hotel & Homes South Beach
President Hotel
1 Hotel South Beach
The Landon Bay Harbor - Miami Beach

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 ideal for family beach holidays, offering a range of activities including sightseeing, fishing getaways, and snorkelling trips. Visitors can enjoy various water sports rentals, while the local shopping centre and area provide ample opportunities for retail therapy. With plenty of outdoor activities available, Islamorada is a perfect destination for those seeking adventure and relaxation by the sea.

Shopping

Discover Rain Barrel Village, a charming shopping spot in Islamorada, filled with unique gifts and local art. If you're up for a drive, consider visiting nearby shopping centres for a broader selection of stores and boutiques to find the perfect souvenirs for your loved ones.

Recreation

Jacob's Aquatic Center, located 27.4km from Islamorada, offers a family-friendly atmosphere with various aquatic activities. Enjoy swimming, relaxation, and fitness in a vibrant environment that caters to all ages, making it a perfect spot for a refreshing wellness retreat.

Adventure

Experience thrilling underwater adventures at Florida Keys Dive Center, located 12.9km from Islamorada, where you can explore vibrant coral reefs. For a unique thrill, visit Keys Cable Park, 35.4km away, for wakeboarding and cable sports. Enjoy the scenic Pa-hay-okee Trail, 38.6km from Islamorada, perfect for hiking amidst lush landscapes.

Nightlife

In Islamorada, enjoy the vibrant nightlife at Jimmy Johnson's Big Chill, a lively pub 27.4km away, perfect for drinks and entertainment. Alternatively, the Caribbean Club Bar, located 33.8km from Islamorada, offers a romantic vibe alongside enjoyable entertainment, making 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 perfect for families seeking outdoor and beach holidays, offering attractions such as marinas, beaches, and national parks. Visitors can enjoy a variety of activities, including exploring the Islamorada Sandbar, relaxing at Islamorada County Park, or venturing through the beautiful Florida Keys. This idyllic destination is ideal for those in search of adventure and memorable experiences by the sea.

  • Anne's Beach: Experience the laid-back charm of Anne's Beach, where soft sands and tranquil waters create the perfect setting for relaxation. Enjoy the beautiful scenery, stroll along the boardwalk, or indulge in a picnic while soaking up the sun.
  • Bud n' Mary's Dive Center: Dive into adventure at Bud n' Mary's Dive Center, a premier marina offering thrilling water activities. Whether you're snorkelling, scuba diving, or fishing, you'll be surrounded by vibrant marine life and stunning coral reefs, making it an outdoor enthusiast's paradise.
  • Islamorada County Park: Enjoy family-friendly fun at Islamorada County Park, featuring playgrounds, sports facilities, and lovely picnic areas. This urban park offers a perfect blend of outdoor activities and city vibes, ideal for spending quality time with loved ones.

Best time to go to Islamorada

The best time to visit Islamorada is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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 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

Take a break from life's daily stresses and relax on your Islamorada holiday. Few things are more rejuvenating than a cool ocean breeze and the sound of waves lapping at the shore. Plan your trip to Islamorada the quick and easy way by locking in one of our Islamorada packages. Many people opt to base themselves near Anne's Beach, a must-see only 10 miles from the downtown area.

Things You Should Know About Islamorada

  • Spend your getaway by the water and let the stresses of daily life drift away with the ocean breeze. Check out our Islamorada beach hotels and indulge in a little beachside bliss.
  • Have a look at Angler's Reef Resort by KeysCaribbean and Blue Water Retreat by RedAwning. These private holiday homes might just be ideal for your stay in Islamorada.
  • Roughly 7,100 people reside in Islamorada. If you're after tips about what to see and do in this area, why not strike up a conversation with some of the friendly locals? Our Islamorada things to do page is also a handy source of information.
  • Islamorada holiday deals are a terrific way to save on exciting experiences. Some ideas, including Theatre of the Sea, Founders Park and Anne's Beach, belong at the very top of your sightseeing list.

Islamorada Essential Information

Language
English
Currency
U.S dollars
Population
7,100
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Theatre of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park

Top hotels in Islamorada

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 £263 per night from 29 Apr to 30 Apr
£263
29 Apr - 30 Apr
includes taxes & fees
9.2/10 Wonderful! (1,310 reviews)
Amazing! Loved everything can’t wait to go back!!

Reviewed on 5 Apr 2026

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 £204 per night from 7 May to 8 May
£204
7 May - 8 May
includes taxes & fees
9.2/10 Wonderful! (1,685 reviews)
We enjoyed our stay. Amenities were goo

Reviewed on 6 Apr 2026

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 £247 per night from 21 Apr to 22 Apr
£247
21 Apr - 22 Apr
includes taxes & fees
8.8/10 Excellent! (1,266 reviews)
Great

Reviewed on 30 Mar 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.

Popular places to visit

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. Flight-inclusive packages are ATOL protected.