Name: Chesapeake Beach Resort
Price range: AU$502
Rating: 9.2

Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Your Islamorada Holiday

With one of our holiday packages to Islamorada, you'll have infinite opportunities for fun and excitement. There's a lot to enjoy, including its laid-back lifestyle and spectacular views. If sightseeing is part of the plan during your trip to Islamorada, visit well-known attractions like Theatre of the Sea, Bud n Marys Dive Centre and Founders Park. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Islamorada holiday plans in motion!

Our guide on where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada

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 Florida Keys Brewing Co. are top sights worth seeing.

Islamorada Holiday

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.

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

Our pick of the best Islamorada Hotel Deals

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

Fully refundableReserve now, pay when you stay

AU$830

12 Mar - 13 Mar

includes taxes & fees

9.2/10 Wonderful! (1,298 reviews)

This Resort is unbelievable from the rooms to the beach, walking & biking trails, golf course 27 acres of lush property. Lots of shops & restaurants nearby including Bass Pro Shop, small artists shops & brewery within walking/biking distance.

Reviewed on 25 Feb 2026

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

AU$502

3 Mar - 4 Mar

includes taxes & fees

9.2/10 Wonderful! (1,658 reviews)

Very comfortable with nice rooms. Attentive on site management.

Reviewed on 27 Feb 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

84001 Overseas Hwy Islamorada FL

Fully refundableReserve now, pay when you stay

AU$792

22 Mar - 23 Mar

includes taxes & fees

9/10 Wonderful! (158 reviews)

Fun outdoor tiki bar. Beautiful beach access. Nice room.

Reviewed on 27 Feb 2026

See all 2,197 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.