Name: Chesapeake Beach Resort
Price range: £306
Rating: 9.2

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.

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

£1,175

per person

26 Mar - 31 Mar

found 10 hours ago

Return direct flight included

London (LHR) to Miami (MIA)

8.4/10 Very Good! (1,001 reviews)

Great location, clean room and beautiful.

Reviewed on 19 Feb 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

£9,510

per person

8 May - 15 May

found 1 day ago

Return flight included

London (LHR) to Miami (MIA)

8/10 Very Good! (1 review)

Hotel Riu Plaza Miami Beach

Mid Beach

Save 100% on your flight

£1,318

per person

8 May - 15 May

found 1 day ago

Return flight included

London (LHR) to Miami (MIA)

8/10 Very Good! (1,120 reviews)

Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on 19 Feb 2026

1 Hotel South Beach

South Beach

Save 100% on your flight

£3,587

per person

2 Apr - 9 Apr

found 1 day ago

Return direct flight included

Edinburgh (EDI) to Miami (MIA)

9.4/10 Exceptional! (1,365 reviews)

Room very nice but not very well designed. Bed and couch on a riser- not the floor- requiring a step up to get to each. Everytime you got up at night- a light would come on and stay on for 10 minutes. Safety so you don’t fall- but should we really have a bed on a riser? Found the light on disruptive to getting back to sleep. Very dark room- not well lit at all. No makeup mirror Slippery marble floor shower- ask for a rubber mat- which we finally got the day before our stay ended Great access to pool and beach Great service in hotel and beach Great service from the house car Very pleasant staff Mini bar beverages not cold- required ice to chill No ice machine- but they brought the ice to you if you called and requested Nice roof top pool but music was too loud to enjoy. Could not eat at Watr restaurant - roof top-due to the loud music Reserved a shower room to freshen up after check out our last day- but did not get one- had to use the gym for getting cleaned up for our flight- lot of disorganization around this entire situation. No one ever offered and explanation on what happened- did not have time to investigate- trying ti get to airport. Great location and vibe- we enjoyed our stay but would not stay here again.

Reviewed on 11 Feb 2026

EAST Miami Residences

Brickell

Save 100% on your flight

£1,878

per person

11 Apr - 18 Apr

found 15 hours ago

Return flight included

London (LHR) to Miami (MIA)

9/10 Wonderful! (84 reviews)

Es la 3 vez que me hospedo y es excelente el trato, la hubicacion y las fascilidades.

Reviewed on 26 Jan 2026

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.0°F (21.1°C)	No Rain	Mostly Sunny	Average	Average
February	71.8°F (22.1°C)	No Rain	Mostly Sunny	Average	Slightly High
March	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
April	76.6°F (24.8°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
July	83.8°F (28.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Average
September	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately Low	Average

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

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

£306

22 Mar - 23 Mar

includes taxes & fees

9.2/10 Wonderful! (1,665 reviews)

Clean room..staff qaa qond

Reviewed on 19 Feb 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

£357

3 Mar - 4 Mar

includes taxes & fees

9.2/10 Wonderful! (1,307 reviews)

Room was very nice and plenty of room. First time visitor. Tub on the balcony was unexpected bonus

Reviewed on 17 Feb 2026

Amara Cay Resort

80001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

£305

8 Mar - 9 Mar

includes taxes & fees

8.8/10 Excellent! (1,261 reviews)

The courtyard and pool area were beautiful! When we arrived, we were told that there would be no boat transportation due to scheduled repairs and we would hear jackhammering in the room from 10 am to 5 pm due to repairs. We were still charged the $70.00 per night resort fee.

Reviewed on 19 Feb 2026

See all 2,211 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.