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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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Chesapeake Beach Resort
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Ranked #14 of 20 Hotels in Islamorada
A recent review
4 of 5 stars reviewed 2 weeks ago
Kathy R Rotonda, Florida, United States
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364 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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Saint Augustine Beach, Florida
19 reviews 19 reviews
3 hotel reviews
3 helpful votes 3 helpful votes
2 of 5 stars Reviewed yesterday NEW

Disappointment with a capital “D.” After prepaying over $200 a night and then a six-hour drive fighting holiday traffic, we found a compound-type property that is sorely lacking in maintenance. A poorly constructed “bar” on the first floor of the two-story tiki was fallling in, the “exercise area” was a tiny outdoor tiki with two ancient, rusted exercise machines and... More

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ft lauderdale, fl
Senior Contributor
31 reviews 31 reviews
10 hotel reviews
16 helpful votes 16 helpful votes
2 of 5 stars Reviewed 1 week ago

We have been coming to the Keys for years and years and never had the opportunity to stay here and have always wanted to. Finally we stayed and we were very disappointed. I will say the front desk staff was very friendly. The property is in dire need of fixing up. The pools were all cracked and needed redoing. The... More

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3 reviews 3 reviews
6 helpful votes 6 helpful votes
1 of 5 stars Reviewed 1 week ago

This have been one of the most horrendous experience in a hotel that we have ever had. The rooms were nasty , the sheets dirty! Hair all over! I called the front desk to complain and they sent the gardener w 2 sheets. The bathrooms outdated/dirty . The best part , the "Fitness center" one bicycle and one bench ,... More

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Rotonda, Florida, United States
20 reviews 20 reviews
3 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed 2 weeks ago

We decided to stay the night in Islamarada after a day trip to the keys. Chesapeake Resort had a room available so there we stayed. The resort is showing some wear. (I stayed there once before many years ago) It was clean. That is the most important thing I look for when I stay the night away from home! My... More

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Harwich, United Kingdom
Senior Contributor
32 reviews 32 reviews
18 hotel reviews
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed 2 weeks ago

After a long drive from Tampa on my way to key west, I just pitched up on a whim. The place was empty after the kids went back to school. Just stayed for a night, but it was a great place to stay. Room was comfortable and cool and well appointed. Facilities were good with 2 swimming pools, tennis courts... More

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Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Once again, the Chesapeake Beach resort has made us ridiculously satisfied. If you're looking for a high-end hotel, keep going. It's a throwback-type motel that you would expect in the 50's or 60's but it really doesn't disappoint. It's quaint and the location is great. Unlike other resorts we've found throughout the Keys, they don't mind you bringing a cooler... More

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Fort Lauderdale, Florida
Senior Contributor
27 reviews 27 reviews
18 hotel reviews
33 helpful votes 33 helpful votes
4 of 5 stars Reviewed 4 weeks ago

My boyfriend and I chose this hotel because we have a 23ft Yamaha and wanted to launch and dock our boat at the hotel where we were staying. Upon arrival, James at the front desk checked us in quickly and our room was ready at 12:00 PM. Upon walking into our garden view room, I was overwhelmed by the smell... More

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Clinton, South Carolina
Senior Reviewer
10 reviews 10 reviews
4 hotel reviews
8 helpful votes 8 helpful votes
2 of 5 stars Reviewed August 9, 2014

This place has so much going for it. The location is incredible. The sunrise is awesome and the grounds and offerings are nice. However they have let the place go. The ocean there smells horrible so I do not recommend swimming in it but the kayaks, paddle boats and other sports shack items are included in your stay. I did... More

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DeBary, Fl
Senior Reviewer
9 reviews 9 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed August 7, 2014

Once again stayed here.. Brought family with us.. We had three seperate reservations.. We had the time of our lives.. You can be as busy or as relaxed as you want. Staff were amazing friendly and attentive. Breakfast was always well stocked. The location is perfect with things to do and restaurants closeby. Rooms were well appointed and if we... More

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jupiter, fl
Senior Reviewer
9 reviews 9 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed August 5, 2014

We usually stay at The Islander but decided to try Chesapeake Beach Resort and we really enjoyed it. Breakfast wasn't just continental. They had eggs/bacon/sausage/waffles etc and it was included in the price as well as their outdoor sports. Kayaks, bikes, paddle boats are all included. At The Islander, you pay $40 to use a Kayak all day and they... 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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