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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
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1 room 1 guest
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485 Reviews from our TripAdvisor 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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Denver, Colorado
Level Contributor
55 reviews
51 hotel reviews
common_n_hotel_reviews_1bd8 29 helpful votes
3 of 5 stars Reviewed 2 weeks ago

The resort could use a bit of updating but was delightful. Breakfast was pretty good and could be enjoyed on the terrace. There were available kayaks and the heated pool was much appreciated. We would stay here again

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New Smyrna Beach, FL
Level Contributor
66 reviews
11 hotel reviews
common_n_hotel_reviews_1bd8 22 helpful votes
3 of 5 stars Reviewed 2 weeks ago

Our first stay here after fifteen plus years at another hotel that greatly raised their rates after renovation. Chesapeake took some getting used to. Like many Keys hotels, it very much needs some repairs, refurbishing and furniture replacement. The balcony furniture was "butt slung" and the finish was flaking off and stuck to your skin. Living room furniture was way... More 

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Sayville, New York
Level Contributor
9 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 16 helpful votes
5 of 5 stars Reviewed 2 weeks ago

Located so conveniently to so many places in Islamorada & just a beautiful establishment. Now please understand I do not seek out large, glamorous, extravagant or ostentatious establishments to vacation at. I prefer clean, locally run, smaller, 'down to earth' venues. Chesapeake Beach was that & more. Our room was charming - overlooking the gulf - I arose to a... More 

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1 review
common_n_hotel_reviews_1bd8 1 helpful vote
2 of 5 stars Reviewed 2 weeks ago

his resort is nothing like its advertised. The entire resort is run down, not well taken care of and the staff very unfriendly especially the front desk staff. We had a 4 day stay and from day 1 the pools were both very dirty and cloudy. After I complained for 2 days, they finally had the pool service come and... More 

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Boynton Beach, Florida
Level Contributor
7 reviews
4 of 5 stars Reviewed 2 weeks ago

Nice place,amenities and a restaurant/bar within walking distance. I'll be back October 2015. Also comes with a continental breakfast. Other restaurants close by and go to Loralie for for dinner and the sunset

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Saint Augustine, Florida
Level Contributor
5 reviews
5 of 5 stars Reviewed 3 weeks ago

Pros-the staff is awesome in the suites on the ocean the king bed was sooooooo comfy and you look out onto the water from your bed they give you a water per person per day, very nice. the couch bed was the worst EVER and the roll a way for 15 a night-you would be better off putting blankets on... More 

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Dallas, Texas
Level Contributor
73 reviews
37 hotel reviews
common_n_hotel_reviews_1bd8 50 helpful votes
4 of 5 stars Reviewed 3 weeks ago

My family stayed in the standard garden view room and in retrospect, I wish we would have gotten an oceanview. The standard room was tiny but it didn't matter much as we didn't spend too much time in our room. The room and grounds were clean and the staff was friendly. The beach area is great for sitting and spotting... More 

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1 review
5 of 5 stars Reviewed 3 weeks ago

We stayed 2 nights in villa 302. It was clean, had a comfortable queen size bed, a sparkling bathroom, fridge and basic needs in the kitchenette! Found little gems throughout the resort when we took our walks around the place and friendly staff keeping the grounds tidy. Breakfast, paddleboards, kayaks all included during the stay making it a really good... More 

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Miami Beach, Florida
Level Contributor
71 reviews
20 hotel reviews
common_n_hotel_reviews_1bd8 37 helpful votes
4 of 5 stars Reviewed 3 weeks ago

Family came in from Boston for a special birthday, and we took 3 ocean front rooms. Very pleasant and comfortable, and the view is lovely. Service seems pleasant and accomodating, and the rooms are well appointed. We are getting a great "keys experience", as the location is close to all activities. Nice for family of all ages.

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Memphis
Level Contributor
17 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 16 helpful votes
4 of 5 stars Reviewed 4 weeks ago

- staff were friendly - rooms, lobby area, breakfast area, pools and beach area were clean. - cold A/C - good breakfast - easy use of the kayaks The reason for the 4 stars instead of 5 is because the property needs some TLC. Also, there were never enough towels. You needed to go ask for them. They were good... More 

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