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Chesapeake Resort

Chesapeake Resort

83409 Overseas Highway
Islamorada, Florida Keys 33036

Written by Ron Ives


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The Chesapeake Resort in Islamorada has been a favorite vacation destination for Florida tourists for more than fifty years. Located in the heart of Islamorada, The Chesapeake offers guests convenient access to all of the favorite local pastimes including fishing, scuba-diving, dining, and shopping. Despite its central location, many choose to spend much of their time relaxing right at the hotel that boasts a private beach, ocean-front pool and Jacuzzi, and an extensive marina facility.

Peaceful Accomodations at the Chesapeake

The Chesapeake owes part of its special charm to its small number of rooms. With only sixty-five rooms including eight suites and thirteen villas, The Chesapeake promises a peaceful and personal vacation experience. Most of the rooms open to breathtaking Wildlife at The Chesapeake views of the ocean and all include a private terrace where guests can enjoy a refreshing afternoon drink before venturing out to enjoy the famous dining and nightlife of the island. All rooms have remote control cable television, quiet air conditioning, double sinks in the bathroom, in-room safes, and personal coffee pots. Other amenities include complimentary continental breakfast, tennis court, child play area, and private gym. Snorkeling in front of the hotel offers underwater explorers a special chance to get up close and personal with the aquatic residents of Islamorada including barracudas, sea rays, and an occasional spiny lobster.

Adventures Beyond the Chesapeake Resort

Adventures abound outside of the hotel including fishing, scuba diving, snorkeling, and kayaking. The famous Pennecamp State Park, located just a few miles north of the hotel, is a favorite destination for picnicking, snorkeling, and scuba diving. Private fishing charters are easy to find and anglers here can expect to catch some of the greatest sportfish in the world including bonefish, tarpon, dolphin, and sailfish. Kayaking the quiet waters of the backcountry is another favorite activity here and guide Lush Gardens at The Chesapeake assisted tours are available. Besides the incredible array of aquatic activities, Islamorada also offers landlubbers a number of activities including dining, dancing, and of course shopping. The nightlife in Islamorada is world renowned for its Jimmy Buffet style of relaxation that has to be experienced to be understood. Don't miss the live entertainment and non-stop party of the Tiki Bar at Holiday Isle. The staff at The Chesapeake is well in tune with the island and happy to help with personalized adventure planning!

Location of the Chesapeake

The Chesapeake Resort is located at 83409 Overseas Highway within walking distance of popular shopping and dining destinations. It is halfway between Miami and Key West, just two hours from both.


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