Chesapeake Beach Resort

Chesapeake Beach Resort The Key to Paradise - A Islamorada Beach Resort

We tried not to have favorites… then Villa 13 happened. 🌊☀️Floor-to-ceiling views, coastal comfort, and the kind of wate...
06/13/2026

We tried not to have favorites… then Villa 13 happened. 🌊☀️

Floor-to-ceiling views, coastal comfort, and the kind of waterfront scenery that makes you want to extend your stay. This is the Florida Keys at its finest.

🏆 We’re honored to be recognized as a Tripadvisor Travelers’ Choice 2026 Award Winner!Thanks to the incredible support o...
06/09/2026

🏆 We’re honored to be recognized as a Tripadvisor Travelers’ Choice 2026 Award Winner!

Thanks to the incredible support of our guests, Chesapeake Beach Resort has been ranked among the Top 10% of hotels worldwide. 🌴🌊

This achievement reflects the dedication of our amazing team and the wonderful experiences shared by our guests every day. Thank you for choosing us, supporting us, and making unforgettable memories in the Florida Keys.

We can’t wait to welcome you back to paradise. ☀️💙

The kind of sunset that reminds you to stay a little longer. 🌴
06/08/2026

The kind of sunset that reminds you to stay a little longer. 🌴

Breakfast by the water. Drinks at the tiki bar. 🌴☀️At Chesapeake Beach Resort, your day starts with a complimentary wate...
06/05/2026

Breakfast by the water. Drinks at the tiki bar. 🌴☀️

At Chesapeake Beach Resort, your day starts with a complimentary waterfront breakfast and ends with tropical cocktails at our beachfront tiki bar. From made-to-order omelets and fresh waffles to sunset views and island vibes, this is how the Florida Keys were meant to be experienced.

Would you set your alarm for this view? 🌅✨ Because every sunrise in Islamorada feels like a reward. 🌊💙
06/04/2026

Would you set your alarm for this view? 🌅✨ Because every sunrise in Islamorada feels like a reward. 🌊💙

🌴 Not all Florida Keys resorts have a beach… we do.Start your morning with a waterfront sunrise, spend the day lounging ...
06/04/2026

🌴 Not all Florida Keys resorts have a beach… we do.

Start your morning with a waterfront sunrise, spend the day lounging on our sandy beach, and end it with unforgettable island sunsets. ☀️🌊

Paradise is closer than you think.

🌴 Looking for a little more privacy on your next Keys getaway?Our private villas offer the perfect blend of comfort and ...
06/02/2026

🌴 Looking for a little more privacy on your next Keys getaway?

Our private villas offer the perfect blend of comfort and seclusion, complete with personalized parking, spacious living areas, and fully equipped kitchens. Just steps from the water, it’s your own slice of paradise in Islamorada.

✨ Would you rather stay in a villa or a traditional hotel room? Let us know below!

🌊 Dreaming of a waterfront celebration? From “I do” to milestone moments, Chesapeake Beach Resort offers the perfect oce...
06/01/2026

🌊 Dreaming of a waterfront celebration? From “I do” to milestone moments, Chesapeake Beach Resort offers the perfect oceanfront setting for unforgettable events. Contact us today to start planning!
305.664.4662 or [email protected] ✨💍🌴

Whether you’re planning a romantic getaway, family vacation, or relaxing island escape, we have the perfect room for you...
05/31/2026

Whether you’re planning a romantic getaway, family vacation, or relaxing island escape, we have the perfect room for you! 🌴🌊

🏝️ Cozy Guest Rooms
🌅 Ocean View Accommodations
🏡 Spacious Suites & Villas
☀️ Private Balconies & Patios
🌴 Steps from the Water

Wake up to breathtaking views, unwind in comfort, and experience the beauty of the Florida Keys.

Which room would you choose for your next getaway? 💙🐬

✨ The little touches make all the difference. ✨A welcome toast 🥂, complimentary popcorn 🍿, and the perfect photo spot 📸—...
05/29/2026

✨ The little touches make all the difference. ✨

A welcome toast 🥂, complimentary popcorn 🍿, and the perfect photo spot 📸—just a few of the ways we make your stay at Chesapeake Beach Resort extra special.

Come for the views, stay for the memories. 🌴💙

ResortLife MakingMemories

Address

83409 Overseas Highway
Islamorada, FL
33036

Website

Alerts

Be the first to know and let us send you an email when Chesapeake Beach Resort posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Shortcuts

Share

Category