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All 20 Islamorada hotels

Chesapeake Beach Resort

2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Ranked #14 of 20 Hotels in Islamorada
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5 of 5 stars reviewed 2 days ago
cindy f jericho, vt
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385 reviews from our community

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Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4 of 5 stars
  • Rooms
    3.5 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4 of 5 stars
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jericho, vt
Senior Contributor
35 reviews 35 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 2 days ago NEW

We rented a bungalow for 3 nights and could not have been happier. The accommodations were clean, comfortable and spacious. The entire resort staff was friendly and helpful. We took advantage of many of the amenities: kayaking, bicycles, swimming were all enjoyable. The shuffleboard area was the only disappointment. I had stayed in this resort several years ago and was... More

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Fort Lauderdale, Florida
3 reviews 3 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed 5 days ago NEW

I coordinated a large group of friends to celebrate my husband's 30th birthday in the keys. We stayed at Chesapeake Beach Resort and it was wonderful. It was close to restaurants. The pool was fabulous and the grounds and rooms are clean and well kept. We did bring a boat into the dock to go out to the sandbar. It... More

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Baltimore, Maryland
2 reviews
1 helpful vote 1 helpful vote
1 of 5 stars Reviewed 6 days ago NEW

Hot tub was out of order, adjoining pool was out of order, construction work in the unit next to ours - hammering started at 7:30AM, toilet clogged, raw sewage backed up into our shower, required to move to a different unit twice without any compensation for our inconvenience. Will not return here!

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Houston, Texas
14 reviews 14 reviews
5 hotel reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed 1 week ago

Just spent three nights at Chesapeake and it was great. First off, this is not The Ritz or a W hotel. If that's your expectation, there are several options in Islamorada. Chesapeake is showing its age a little, but overall the resort is clean, the staff is friendly, and the cost is in line with other Keys resorts. Do pay... More

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2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed 2 weeks ago

The Chesapeake Resort is the finest resort I have ever stayed at. The rooms were clean and smelled fresh. The tropical landscaping and the property are immaculately maintained. It has an excellent free breakfast buffet with an excellent selection. The staff is courteous and friendly. It is close to many fine restaurants and attractions and a trip to Key West... More

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2 reviews
1 helpful vote 1 helpful vote
1 of 5 stars Reviewed 3 weeks ago via mobile

First off our door didn't close all the way. There were bugs that were coming in with the door closed. We had the doors closed all day and somehow had ants that made their way in and were crawling on the dressers. To top it off there was absolutely the loudest festival that was going on in the lot next... More

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White Oak, Georgia
Senior Contributor
33 reviews 33 reviews
5 hotel reviews
17 helpful votes 17 helpful votes
4 of 5 stars Reviewed 3 weeks ago

We've been vacationing the Florida Keys for 16 years so we've stayed in pretty much all the island and different hotels/ resorts but so far Cheasapeake Beach Resort has the BEST LOCATION. We didn't need to go somewhere else the beach and ocean for swimming were right there. I really loved the atmosphere, the hammock around the property, beach and... More

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Lake Worth, Florida
13 reviews 13 reviews
7 hotel reviews
14 helpful votes 14 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Went back to visit Islamorada and Chesapeake Beach Resort for our third visit and loved it just as much as the first 2 times. Had on ocean view room that didn't disappoint. Breakfast was nice and convenient again. Made use of the pool and hammocks and especially the kayaks. The weather was perfect and the ocean was flat so it... More

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Ann Arbor
Senior Reviewer
7 reviews 7 reviews
3 hotel reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed 3 weeks ago

A girlfriend and I stayed for three nights in a garden view room and were very happy with our choice. The room was clean and the AC worked great. I loved the grounds with many areas to sit and hang out. I would stay here again for sure. This would be a very fun place for a large group as... More

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Boston, Massachusetts
Senior Contributor
38 reviews 38 reviews
18 hotel reviews
96 helpful votes 96 helpful votes
4 of 5 stars Reviewed 3 weeks ago

Location - midway to Key West. Can be a good base of exploration. Once the new restaurant goes in next door it should be a great spot.... for now there will be some construction coming. BUT Wahoos is still a great authentic spot to walk to for lunch, drinks, dinner --- and the bars and dining of the MUCH pricier... More

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Additional Information about Chesapeake Beach Resort

Address: 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Phone Number:
Location: United States > Florida > Florida Keys > Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
Number of rooms: 65
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Also Known As:
Chesapeake Beach Hotel Islamorada

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