Chesapeake Beach Resort

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

10/15/2026

🌴 We’re not the only ones enjoying paradise! 💙 Even the manatees love stopping by Chesapeake Beach Resort! 🐋🌊

You never know what kind of visitor you’ll spot in our beautiful Florida Keys waters! ☀️

10/14/2026

From your room balcony to our marina and private beach… paradise is just a few steps away! 🌴🌊☀️

Imagine waking up to these views, enjoying your morning overlooking the ocean, and spending the rest of your day with your toes in the sand. 🏝️💙

✨ No need to leave the resort when everything you need for a perfect Keys getaway is right here!

😍 Which is your favorite: the balcony views, marina, or private beach? 👇

10/11/2026

POV: You found your own little slice of paradise in the Florida Keys! 🌴☀️🌊

Private beach, swaying palms, breathtaking waterfront views, and absolutely nowhere else you’d rather be! 😍💙

✨ Tag someone who needs a getaway to Chesapeake Beach Resort!

📍 Islamorada, Florida Keys

VacationMode

10/04/2026

We love seeing Chesapeake Beach Resort through our guests’ eyes! 🌴💙 Even a rainy weekend in the Florida Keys can’t take away from the beauty, relaxation, and memories made at Chesapeake. 🌧️🌊

Thank you for sharing your experience with us — guest videos like this truly make our day!

09/30/2026

Even rainy days are beautiful at Chesapeake Beach Resort. 🌧️🌊 There’s something peaceful about watching the storm clouds roll across the ocean from your front-row seat in the Florida Keys. 🌴🤍

09/25/2026

Drone view of our beautiful Islamorada Property 🐬

Chesapeake kind of afternoon 🌴🌊☀️ Where the palms sway, the water sparkles, and relaxation comes naturally.
09/17/2026

Chesapeake kind of afternoon 🌴🌊☀️ Where the palms sway, the water sparkles, and relaxation comes naturally.

A fresh first impression 🌴✨ Our newly landscaped entrance is coming together beautifully! Welcome to Chesapeake Beach Re...
09/15/2026

A fresh first impression 🌴✨ Our newly landscaped entrance is coming together beautifully! Welcome to Chesapeake Beach Resort—where your Florida Keys escape begins the moment you arrive. 🌊☀️

WelcomeToParadise

09/14/2026

What could be better than a beach trip at Chesapeake Beach Resort? 👀

Address

83409 Overseas Highway
Islamorada, FL
33036

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