Islamorada Holidays from £805

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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.
Pelican Hotel

Pelican Hotel

South Beach
£805
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Miami (MIA)
9.2/10 Wonderful! (492 reviews)
The Penguin Hotel

The Penguin Hotel

South Beach
£879
per person
8 Nov - 15 Nov
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very good! (1,938 reviews)
EAST Miami

EAST Miami

Brickell
Save 100% on your flight
£1,503
per person
23 Oct - 30 Oct
found 3 hours ago
Return flight included
London (LGW) to Miami (MIA)
9.2/10 Wonderful! (4,025 reviews)
Fontainebleau Miami Beach

Fontainebleau Miami Beach

Mid Beach
Save 100% on your flight
£1,345
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
Glasgow (GLA) to Miami (MIA)
8.4/10 Very good! (8,706 reviews)
Love. Love. Love. This hotel. Every time I’m in Miami I call Fontainebleau home.

Reviewed on 22 Aug 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

Mid Beach
£1,023
per person
23 Oct - 30 Oct
found 3 hours ago
Return flight included
London (LGW) to Miami (MIA)
8.2/10 Very good! (1,169 reviews)
Property and staff were fantastic, buffet was delicious but Linda pricy for someone who’s not eating more than the necessary. Amenities were ok, pool is small for the amount of people at the hotel; if you lucky the beach would be clean and you can enjoy the beach. Other than that is an okay location for relaxing.

Reviewed on 19 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.

Find hotels in Matecumbe
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.

Find hotels in Venetian Shores
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.

Find hotels in Lower Matecumbe 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.

Find hotels in Seabreeze Trailer Park

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

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
£176
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,418 reviews)
"It was very relaxing and peaceful, and the boys worked very hard for the guests"

Reviewed on 22 Aug 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£165
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,761 reviews)
"Amazing breakfast, clean room and very friendly staff."

Reviewed on 21 Aug 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
£174
3 Sept - 4 Sept
includes taxes & fees
Amara Cay Resort
See all 2,166 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.
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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.
See properties
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.
See properties
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 building with a blue facade, a large mural of a diving scene, and a statue of a diver.

History of Diving Museum

9.0/10 (177 reviews)
Discover 4,000 years of underwater exploration at this unique museum featuring diving helmets from around the world. Explore exhibits showcasing the evolution of diving technology from ancient to modern times.
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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

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour

£52
per adult
Tavernier, FL: Mangrove and Manatees Guided Kayak Eco Tour
Explore Mangrove Creeks with an All Day SUP/single kayak Rental

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

£37
per adult
80% of travellers recommend
Explore Mangrove Creeks with an All Day SUP/single kayak Rental
Islamorada Sunset Cruise with Champagne Toast and Snacks

Islamorada Sunset Cruise with Champagne Toast and Snacks

£53
per adult
80% of travellers recommend
Islamorada Sunset Cruise with Champagne Toast and Snacks
See all activities in Islamorada

Frequently asked questions

Why should I book my Islamorada holiday with Expedia?
Expedia has your back for every detail of your next Islamorada trip. You'll always get the best prices around, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll score even more savings. Want to truly make the most of your escape? Add a few exciting activities and tours to your package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Islamorada?
Islamorada is a popular place in November, December and January. If you're not into large crowds and prefer a calmer pace, book your escape for April, September and October. To get an idea of the type of weather to expect, the average temperature during the day in January, the coolest month in Islamorada, is 21ºC. The warmest period here is August, when temperatures reach around 29ºC.
What are the top hotels for my holiday in Islamorada?
If you'd like to stay in the Venetian Shores neighbourhood, Postcard Inn Beach Resort & Marina and Sunset Inn are in-demand options. Lower Matecumbe Beach is another well-known Islamorada area. We recommend Sunset Inn or Islander Resort if you prefer this part of town.
How do I get a cheap holiday to Islamorada?
Bundle your flights and hotels with Expedia to save on your next getaway. With more than 400 airlines and 321,000 hotels globally, your Islamorada holiday can be tailored exactly to suit your travel style. With all that extra money, why not add a few awesome activities and tours? It's an easy way to unlock even more savings. Your dream getaway to Islamorada is closer than you thought! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Islamorada holiday?
There are so many places to check out while having a holiday in Islamorada. Theatre of the Sea, Annes Beach, Bud n Marys Dive Centre and Founders Park are among this destination's key attractions.
What is the best area to stay in when on holiday in Islamorada?
If you plan to check out Theatre of the Sea, maximise your time sightseeing and lock in a stay close by. It's one of the most popular attractions in Islamorada.
Do I need a visa for my Islamorada holiday?
Research the latest information on official government websites. Your nationality and whether you're travelling for business, study or leisure will determine if you'll need a visa for Islamorada. Get familiar with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow enough time for processing. Some visas can take many weeks or even months to obtain, depending on the country.
What should I wear on my Islamorada holiday?
First, think about the types of things you'll be doing during your Islamorada holiday and select versatile pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, look up style blogs or relevant social media accounts. Pack your bags with confidence by monitoring the local weather conditions in Islamorada. August brings the warmest temperatures, with daytime averages of 29ºC, while January days average 21ºC, making it the coolest time of the year.
What does an Expedia Islamorada holiday include?
Hotels, flights and a cool set of wheels for all your road trip adventures. Simply pick and choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to organising your Islamorada break, you're the boss! Explore a wide range of property types and pick one that suits your group size and travel needs. The most in-demand rentals here are private holiday homes and condos. With Expedia, it's easy to tailor-make your Islamorada escape however you want.
Does Expedia offer Book Now, Pay Later Islamorada holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fabulous getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:
  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable payment plans. If paying across multiple instalments works for you, pick this option at checkout.
  • No-deposit holidays: When you see an unbeatable deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.
Can I choose my airline with an Islamorada Expedia holiday?
Yes, you're in control. We have access to over 400 partner airlines around the world, so you can design your Islamorada holiday according to your travel needs.

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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.