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Chesapeake Beach Resort

2.5 of 5
Hotel website
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Special Price
15% off room rate
Chesapeake Beach Resort
Best prices for: 1 room 1 guest
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Ranked #15 of 20 Hotels in Islamorada
A recent review
4 of 5 stars reviewed 4 days ago
cubanaminnesotana Lake City, Minnesota
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445 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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Lake City, Minnesota
1 review
4 of 5 stars Reviewed 4 days ago NEW

My husband and I spent 9 nights at this resort. We stayed at a one-bedroom villa and enjoyed excellent service. The bathroom was kind of small - everything else was satisfactory and very clean. We liked being on the ground level with easy access to the beautiful grounds with a private beach and two swimming pools. There is a mandatory... More 

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Henrietta, New York
Senior Contributor
24 reviews 24 reviews
7 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed 1 week ago NEW

My family and I choose this resort because it was affordable and ideal for our needs. We don't care for the larger resorts because they are too touristy. The view from our beach front suit was so lovely and pretty enough to put on a postcard. The continental breakfast was all we needed before starting our day, we cooked in... More 

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Toronto, Canada
Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 1 week ago

I am back for another week at this beautiful resort. It is place to unwind, relax, leave your troubles at home and enjoy the resort with all its amenities. I have a room overlooking the sea, the view is breakthtaking, approx. 200 palm trees on 6 and half acres with exotic plants and flowers. Later on I will go out... More 

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Des Plaines, Illinois
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed 1 week ago

Let me first say, I am a bit of a Hotel-a-phobe, meaning I can't stand staying in them and get creeped out easily so anything i review is exactly as it is.We stayed here one night on the way to visit friends further down the island. We arrived late and left fairly early but were happy with what we saw.... More 

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West Palm Beach, Florida
Senior Reviewer
8 reviews 8 reviews
4 hotel reviews
11 helpful votes 11 helpful votes
3 of 5 stars Reviewed 2 weeks ago

Have been to this resort many, many times in last twenty years. Its a great clean property and all ocean front rooms have a stunning view. The rooms have been redone but my bathroom showed some wear. Bedroom/balcony was clean and very good. 2 pools, very spread out which gives uncrowded feeling, many palm trees for shade and docks for... More 

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Boynton Beach, Florida
Contributor
13 reviews 13 reviews
7 hotel reviews
7 helpful votes 7 helpful votes
3 of 5 stars Reviewed 2 weeks ago

Stayed here a few years back. Was well kept, clean, and worth a return visit. Not so much now and definitely not for the asking price. Most everything getting long-in-tooth or sadly neglected. From the bathrooms, the tiki hut, the patio furniture, the dirty 'bay' area, to the building structures themselves - so much potential with the fantastic location -... More 

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Miami, Florida
Senior Contributor
34 reviews 34 reviews
9 hotel reviews
17 helpful votes 17 helpful votes
4 of 5 stars Reviewed 3 weeks ago

I was in Islamorada for work and decided to stay the night rather than driving back home late at night. I drove by the Chesapeake and there was a vacancy sign out. Usually in the keys if there is a vacancy sign out on a Saturday you know something is wrong with a hotel. I decided to stop anyways and... More 

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Sunrise, Florida
1 review
4 of 5 stars Reviewed 3 weeks ago

We loved the atmosphere. We stayed for 2 nights and enjoyed every minuet of it. The kids enjoed the water activities that were included in the cost of rental. The resort is average and suitable to average guest. the staff were Very nice and helpful.

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Senior Reviewer
9 reviews 9 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed 4 weeks ago

my wife and I chose this resort based on property and reviews. Islamorada is our favorite of all the Keys. Its a little more peaceful and quiet than some of the others. We had some concerns about this resort not having a bar or restaurant, but those concerns were quickly swept away once we realized how much quieter the property... More 

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Grande Prairie, Canada
Reviewer
5 reviews 5 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed April 21, 2015

If you are looking for the Crowne Plaza, this is not it. However, this resort is neat, clean, well taken care of (albeit older, but you ARE in the Keys-which IS historical!) After reading some reviews, we were actually a bit worried, but once we got there and checked out the beautiful grounds, we felt right at home. The breakfasts... More 

Was this review helpful? Yes 2
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