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Chesapeake Beach Resort

2.5 of 5
Hotel website
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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15% off room rate
Chesapeake Beach Resort
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Ranked #14 of 20 Hotels in Islamorada
A recent review
5 of 5 stars reviewed yesterday
Geno F
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434 reviews from our community

Traveler rating
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122
184
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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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Senior Reviewer
9 reviews 9 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed yesterday NEW

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 1 week ago NEW

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 

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Senior Reviewer
6 reviews 6 reviews
3 helpful votes 3 helpful votes
4 of 5 stars Reviewed 1 week 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
18 reviews 18 reviews
6 hotel reviews
13 helpful votes 13 helpful votes
4 of 5 stars Reviewed 1 week 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
Aiken SC
Senior Contributor
21 reviews 21 reviews
19 hotel reviews
11 helpful votes 11 helpful votes
4 of 5 stars Reviewed 1 week ago

The reviews on this hotel varied so we did not know what to expect. Overall, it is a very nice hotel. The hotel rooms are small, but they are clean. The property is well maintained. We thought the views were just beautiful. There was plenty for the kids to do and the two pools were very nice. I did not... More 

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San Jose, California
Senior Contributor
23 reviews 23 reviews
4 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed 2 weeks ago

We really enjoyed staying at the Chesapeake Beach Resort. The grounds were very well maintained. We were in a recently renovated room with beach and ocean views and it was just perfect. We had a king size bed and breakfast was included each morning!

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Philadelphia, Pennsylvania
Senior Reviewer
6 reviews 6 reviews
3 hotel reviews
13 helpful votes 13 helpful votes
5 of 5 stars Reviewed 2 weeks ago

The grounds are well manicured with sitting areas dotted artistically throughout the property. Beauty everywhere you turn. Traveling with my parents we booked the two bedroom villa that was incredibly roomy! We had two full baths, a galley kitchen, dining area, wet bar (with sink), coral wall and a very large living room with 2 queen sleeper sofas. But, what... More 

Was this review helpful? Yes 1
San Luis Obispo County, California
Reviewer
5 reviews 5 reviews
4 hotel reviews
4 helpful votes 4 helpful votes
3 of 5 stars Reviewed 3 weeks ago

This is a lovely older beach front property. The staff are fantastic & the amenities great. However, it sits about 10 feet off the highway, the walls & doors are extremely thin, & the plumbing screeches all night. I might stay here again because the location is great, but take your earplugs!

Was this review helpful? Yes 1
Cape Cod
Top Contributor
55 reviews 55 reviews
7 hotel reviews
21 helpful votes 21 helpful votes
3 of 5 stars Reviewed 3 weeks ago

The Chesapeake Bay Resort looks "good from far, but far from good", which is to say "don't be swayed by an aerial view on a brochure or web site.". It needs a large injection of money so the rooms don't look like the 70s and the amenities are in keeping with the room price. The problem for consumers is that... More 

Was this review helpful? Yes 1
Canton
Senior Contributor
38 reviews 38 reviews
8 hotel reviews
13 helpful votes 13 helpful votes
5 of 5 stars Reviewed 3 weeks ago

This hotel has a variety of room types. We stayed in a garden view room on the second floor. It was clean and well cared for. The room had a screened in balcony overlooking the tennis courts and some nice foliage. Breakfast had both hot and cold items and we sat outside at a table to eat. Food was comparable... More 

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