Islamorada Holidays

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Top Flight + Hotel Deals in Islamorada

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel

Pelican Hotel

South Beach
€1,003
per person
5 Oct - 11 Oct
found 19 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.2/10 Wonderful! (492 reviews)
unique character and great staff!

Reviewed on 18 Aug 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

Mid Beach
€1,469
per person
5 Oct - 11 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very good! (8,706 reviews)
Viscay Hotel

Viscay Hotel

South Beach
€4,216
per person
5 Nov - 12 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand

Reviewed on 16 Jul 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

Mid Beach
€1,082
per person
5 Oct - 11 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.2/10 Very good! (1,169 reviews)
To many people, staff mostly only spoke spanish and everything was expensive

Reviewed on 18 Aug 2026

1 Hotel South Beach

1 Hotel South Beach

South Beach
€5,718
per person
5 Nov - 12 Nov
found 21 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Everything was perfect. Stayed here before and will stay again!

Reviewed on 18 Aug 2026

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.

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.

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.

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.

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

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
€208
19 Aug - 20 Aug
includes taxes & fees
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
€195
19 Aug - 20 Aug
includes taxes & fees
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
€226
23 Aug - 24 Aug
includes taxes & fees
Amara Cay Resort
See all 2,170 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 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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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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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

€62
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

€97
per adult
Snorkel and Sandbar Combo Adventure in Islamorada
Explore Mangrove Creeks with an All Day SUP/single kayak Rental

Explore Mangrove Creeks with an All Day SUP/single kayak Rental

€43
per adult
80% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
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 from €1,003 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.