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
A pier extending into calm waters with a covered seating area and a sandy beach.

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Robbie’s of Islamorada are top sights worth seeing.

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A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Islamorada County Park and Founders Park.

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A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.

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A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like Founders Park and Islamorada County Park.

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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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
S$323
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (1,371 reviews)
"My family had a wonderful time. We took advantage of the bikes, fishing, kayaks, kids club, etc. Will def be coming back!"

Reviewed on 7 Aug, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
S$283
7 Sept - 8 Sept
includes taxes & fees
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
S$329
9 Aug - 10 Aug
includes taxes & fees
Amara Cay Resort
See all 2,169 properties in Islamorada
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.

Stay near popular Islamorada attractions

A sandy beach with green vegetation and a calm sea.

Anne's Beach

7.8/10 (597 reviews)
Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
The Upper Keys' first microbrewery infuses local flavours like Key lime and honey into its craft beers. Sip seasonal brews in the vibrant taproom or lush beer garden while enjoying local art and live music.
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A small green leaf growing on a rough, textured surface.

Windley Key Fossil Reef Geological State Park

8.8/10 (184 reviews)
Walk through ancient coral walls rising eight feet high in this former limestone quarry turned state park. Ranger-guided tours reveal the fascinating geological history preserved in the fossilised reef.
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Robbie’s of Islamorada

8.4/10 (15 reviews)
Explore the waterfront in Islamorada with a trip to Robbie’s of Islamorada.
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Islamorada County Park

8.8/10 (198 reviews)
This 40-acre waterfront retreat offers a bayfront beach, marina, and scenic trails for active relaxation. Enjoy a refreshing swim in the pool or bring your four-legged friend to the specialised dog parks.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
The Florida Keys' first distillery crafts award-winning spirits and beers capturing the island's essence. Enjoy tastings in their relaxed taproom or pet-friendly garden with pub-style food available.
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Sunset Drive Beach

9.0/10 (91 reviews)
This secluded stretch of Islamorada shoreline offers a peaceful retreat from Florida's busier beaches. Watch the sky transform into a canvas of colours as the sun sinks into the Atlantic Ocean.
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What to do in Islamorada

Islamorada Sunset Cruise with Champagne Toast and Snacks

Islamorada Sunset Cruise with Champagne Toast and Snacks

S$92
per adult
80% of travellers recommend
Islamorada Sunset Cruise with Champagne Toast and Snacks
Snorkel and Sandbar Combo Adventure in Islamorada

Snorkel and Sandbar Combo Adventure in Islamorada

S$144
per adult
Snorkel and Sandbar Combo Adventure in Islamorada
Mangroves and Manatees - Guided Kayak Eco Tour

Mangroves and Manatees - Guided Kayak Eco Tour

S$89
per adult
92% of travellers recommend
Mangroves and Manatees - Guided Kayak Eco Tour
See all activities in Islamorada

Frequently asked questions

How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Islamorada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Islamorada?
You can generally find lower prices and greater availability in September, October and November. Browse our cheap Islamorada holiday packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We'd recommend booking an Islamorada holiday for at least 3 days. This will give you enough time to visit top attractions such as Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, and explore neighbourhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a holiday package to Islamorada?
Islamorada has all the ingredients you need for a fantastic getaway — walking trails, views and family-friendly attractions are just the start. Whether you'd like to check out attractions such as Theatre of the Sea and Hurricane Monument, or take the path less traveled, there's plenty to see and do on your Islamorada holiday.
How to find the best Islamorada package deals?
Use Expedia's filter tool to help you find some tempting Islamorada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Islamorada package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book an Islamorada holiday as a package?
You can enjoy significant savings on your Islamorada escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Islamorada?
If you're considering a spur-of-the-moment Islamorada getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Islamorada?
  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Islamorada.
  2. Set your budget: Factor in expenses like food, flights and transportation when working out how much to save for your trip to Islamorada. Then, select a hotel that works with your budget, whether that's a low-cost option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend exploring Islamorada. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Islamorada holiday package for you.

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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.