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Aerial view of a coastal resort with a lagoon, surrounded by lush greenery and clear blue skies, featuring sandy beaches and buildings.

The Key to Paradise

Islamorada Beach Resort

It’s not often you find a resort that exceeds your wildest dreams. Chesapeake Beach Resort takes everything you’ve ever wanted in a seaside vacation and places it in one scenic, majestic location.

Celebrated as the Sport Fishing Capital of the World, Islamorada’s relaxed atmosphere provides an unmatched year-round destination.

  • A sunset over a tropical beach with palm trees viewed from a wooden balcony, creating a serene and picturesque scene.
  • A bright and modern bedroom with a large bed, a ceiling fan, a view of palm trees, and a balcony overlooking a scenic beach setting.
  • A balcony overlooking a serene beach with palm trees, clear blue water, and a bright sky with a few clouds.
  • The image shows a beautiful beach scene with tall palm trees, white sandy shores, lounge chairs, and a calm blue ocean under a clear blue sky with scattered clouds.
    • A modern living room with neutral sofas, a striped rug, and large windows revealing an ocean view. It has cozy seating and a ceiling fan.
    Modern living room with sofa, TV, ceiling fan, balcony, and ocean view
    Modern living room with sofa, TV, balcony view, and ceiling fan.
    Modern living room interior with sofa, table, TV, and balcony view.

    Island Dreams. Relaxation. Comfort

    WHAT MORE DO YOU NEED

    Every room has big comfortable beds, and a serene, tranquil atmosphere. Choose a Garden View room and take advantage of the private balcony. Or for true luxury book a suite or villa, great for long term stays or large groups and families.

    Rooms & Suites

    Experience the Majestic Keys

    LIFE IS BETTER IN FLIP FLOPS

    The Chesapeake Beach Resort is surrounded by pure blue waters, powder white sand, and gorgeous sunshine.This is life on the water, relaxing, enticing, and breathtaking. Just a couple of minutes from Sandbar Islamorada, Theater of the Sea, Anne’s Beach and Full Moon Party at Pierre’s Restaurant & Morada Bay.

    Explore Islamorada

    Palm trees, white sandy beach, lounge chairs, and a turquoise ocean under a blue sky with a few clouds create a tropical paradise scene.
    Palm trees, white sandy beach, lounge chairs, and a turquoise ocean under a blue sky with a few clouds create a tropical paradise scene.
    This image shows an outdoor event setup on a beach with round tables and chairs under palm trees, overlooking the ocean.
    An outdoor beach wedding setup with white chairs, an aisle runner, a decorated arch, chalkboard signs, and palm trees against a sea backdrop.
    A picturesque beachfront property with palm trees, modern buildings, a pool, and a calm body of water in the foreground, on a sunny day.
    A group of people practicing yoga on blue mats in a sandy outdoor area with palm trees and a modern building in the background.

    Plan the Perfect Event

    AN OCEANFRONT VENUE

    Turn your next event into a picture-perfect moment. When you book your wedding, reunion, meeting, or retreat at Chesapeake Beach Resort, you’ll enjoy crystal blue perfection on the beach, with affordable rates, great food and drink, and the kind of sea-salt sensations that you can only get in the Florida Keys.

    Learn More

    Resort Highlights

    • 2024 Newly renovated resort
    • Two outdoor pools with ocean views
    • All rooms have balconies with ocean or island views
    A person wearing a wide-brimmed hat relaxes by a pool, their legs stretched out towards the water.

    UP TO 20% OFF RATES

    Get the lowest rates guaranteed when you book here.

    BOOK NOW

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