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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
5 of 5 stars reviewed 2 days ago
birgittemelnick Toronto, Canada
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443 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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Toronto, Canada
Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed 2 days ago NEW

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
4 reviews 4 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed 3 days ago NEW

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 1 week 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 

Was this review helpful? Yes 1
Miami, Florida
Senior Contributor
34 reviews 34 reviews
9 hotel reviews
17 helpful votes 17 helpful votes
4 of 5 stars Reviewed 2 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 3 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 

Was this review helpful? Yes 1
Grande Prairie, Canada
Reviewer
5 reviews 5 reviews
4 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 4 weeks ago

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
Senior Reviewer
6 reviews 6 reviews
4 helpful votes 4 helpful votes
4 of 5 stars Reviewed 4 weeks ago via mobile

My husband and I stayed here for our 10th anniversary. It's not the nicest place we stayed at, but it was still nice. The place is a bit dates, but it is clean and well maintained. They had hot breakfast daily, which was included in the room rate. It was nothing fancy, but it was nice to not have to... More 

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Utica, New York
Contributor
19 reviews 19 reviews
7 hotel reviews
15 helpful votes 15 helpful votes
4 of 5 stars Reviewed 5 weeks ago

We picked this resort based on price and Trip Advisor reviews. We stayed for 2 days in April to do some diving and relaxing. Resort seemed a bit older but in great repair. Rooms were clean and comfortable with nice furnishings. Included a fridge and coffee maker. There was also a nice little screen porch outside of our room. Resort... More 

Was this review helpful? Yes 1
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