A beachfront building with multiple stories, palm trees, and clear blue skies by a calm body of water under a few scattered clouds.

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.

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.

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

Open