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The Florida Keys Hotels

Chesapeake Beach Resort

  • 83409 Overseas Hwy. Map It
  • Upper Matecumbe Key
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  • Oceanfront location
  • Free use of water-sports equipment and Wi-Fi (included in resort fee)


  • Dated exterior
  • Mandatory resort fee (per room per night)

Updated 07/15/2014

Fodor's Review

This boutique hotel on the beach mixes modern conveniences with a retro look. High-tech gadgets like flat-screen TVs, CD players, and MP3 players give the place an up-to-date feel. Coral stone and dark wood accent the rooms, each of which has a porch or a balcony. Most units are lined up along the long stretch of sand that all but encircles a lagoon; others overlook the tennis court. Room service available only from 11:30 am to 9:30 pm.

Hotel Information


MM 83.5, 83409 Overseas Hwy., Islamorada, Florida, 33036, United States

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305-664–4662; 800-338–3395

Hotel Details:

  • 44 rooms, 8 suites, 13 villas
  • Rate includes Breakfast

Updated 07/15/2014

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Fodorite Reviews

Average Rating
  • Room

  • Décor

  • Service

  • Value

May 10, 2013

KEEP LOOKING FOR BETTER, there much nicer places in the KEY's!!

the best $400/night villa was outdated, dirty, bathroom was gross, simple thing like metal rail inside villa between the rooms that was thin and cut bottom of bare feet.. not worth it at all.. Then there is the main reason we chose this resort was because of the watersport items pictured in website and when talking to receptionist on the phone I wanted to confirm they had enough kayaks and Paddle Boards to go around with limited time I wanted to

be sure of this.. Got there and there was ZERO paddle boards and only single person 200 lb. weight limit kids size kayaks.. both my parents whom I purchased this trip for could not use any of the provided items because they are kayaks ment for CHILDREN.. Guy at watersports desk was an absolute RUDE PERSON, talked to me like I was some kind of "watersports" NOT SMART PERSON.. needless to say I live on gulf coast of florida and own 3 kayaks and paddle boards so i'm not some NOT SMART PERSON tourist who wouldn't know the difference between the large size TRIBE kayak pictured on the website and the ALOHA piece of garbage kayaks he had on hand. KEEP LOOKING, THIS PLACE SUCKS.. all attempts to complain to a manager have been un-answered.. Wording may sound weird, but i had to edit it to get it accepted

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