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Chesapeake Beach Resort

2.5 of 5 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Chesapeake Beach Resort
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412 reviews from our community

Traveler rating
    125
    162
    63
    32
    30
See reviews for
116
170
13
5
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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Princeton, New Jersey
Contributor
12 reviews 12 reviews
4 hotel reviews
3 helpful votes 3 helpful votes
4 of 5 stars NEW

for $209, the villa did the trick. It was spacious, with a living area, full kitchen and bath. I would pick this every time over the hotel rooms, though I didnt see them! Just to have your own little space at a reasonable rate was fine by me. The pool looked clean and nice. The dock and beach area were... More 

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guangzhou china
Top Contributor
57 reviews 57 reviews
9 hotel reviews
24 helpful votes 24 helpful votes
4 of 5 stars Reviewed 4 days ago NEW

Chesapeake is an older resort but well kept and very clean. Kayaks,bikes and sport equipment available, Two pools, gorgeous views. We got several great restaurant sandwich,etc tips from the staff. I would definitely stay there again. It is not a high end resort but it is a clean, comfortable, reasonably priced accommodation for the keys.

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Middleton, Massachusetts, United States
Contributor
15 reviews 15 reviews
4 hotel reviews
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed 1 week ago

This resort was wonderful! Our room had a beautiful ocean view and the sunrise was spectacular. The kayaks were great and the man running the "toys" shack was helpful and nice. All the staff were friendly. My grandson and son loved the heated pools but I have to say the resident Iguanas were the most entertaining of all! The breakfast... More 

Was this review helpful? Yes 1
Regina, SK. Canada
Senior Contributor
31 reviews 31 reviews
22 hotel reviews
54 helpful votes 54 helpful votes
4 of 5 stars Reviewed 1 week ago

We loved our stay! We had a great view of the garden and a short walk to the pools and beach area. The rooms are well equipped and the location of the hotel makes for easy driving to explore the Keys. We loved the opportunity for a quick breakfast too

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illinois
Senior Contributor
29 reviews 29 reviews
9 hotel reviews
32 helpful votes 32 helpful votes
5 of 5 stars Reviewed 1 week ago

Four of us shared a two bedroom cottage, and had a great time. When the sun is shining, it really is as pretty as all the pictures show. Even though they were booked full, it never seemed crowded anywhere, and getting to the pool or to breakfast was always easy.. We ate breakfast outside every morning, and this is February.... More 

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Saint Paul, Minnesota
Top Contributor
90 reviews 90 reviews
17 hotel reviews
24 helpful votes 24 helpful votes
4 of 5 stars Reviewed 1 week ago

We wish we had stayed longer! I could go on about the little things that need updating or repair like the misaligned bathroom light or sagging toilet paper holder, but the place was clean & the staff were very friendly & we couldn't ask for more. They have great amenities like two pools, free kayaks & paddle boats, playground, tennis... More 

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Freeport, Maine
Senior Reviewer
8 reviews 8 reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We rented a cottage for a week in the middle keys and wanted to extend our stay before heading back to Maine. We chose the Chesapeake because we stayed there before and were pleased. The checkout time at our cottage was 10:00 am so we drove to the Chesapeake to see if they would be able to give us an... More 

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Woodbury, Connecticut
Senior Contributor
38 reviews 38 reviews
5 hotel reviews
18 helpful votes 18 helpful votes
5 of 5 stars Reviewed 2 weeks ago

My wife found this "resort" on the internet and it looked good. It has reasonable rates, comfortable rooms, and a beautiful location. We were not disappointed. The breakfast, as said before, was full, scrambled eggs, sausage, bacon, fruit, waffles, etc. We were in the garden rooms and had a screened in porch in the back of the room, which was... More 

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Westport, Ireland
Top Contributor
87 reviews 87 reviews
23 hotel reviews
43 helpful votes 43 helpful votes
3 of 5 stars Reviewed 2 weeks ago

We decided to stay here because it had been recommended. We had a room with a balcony overlooking the small harbour and the Atlantic. The room was, as many have already said, tired-looking. However it was clean, spacious, the beds were very comfortable and the free WiFi was relatively fast. Also free parking directly under the room was very convenient.... More 

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Contributor
12 reviews 12 reviews
7 hotel reviews
6 helpful votes 6 helpful votes
3 of 5 stars Reviewed 2 weeks ago

This is a limited resort which is too expensive for what you get. Our room was clean and comfortable with good balcony and comfortable beds. The bathroom was small and old-fashioned with limited surface to put toiletries. It was very pleasant and relaxing, lounging beside one of the 2 pools or by the ocean with a beautiful view of the... More 

Was this review helpful? Yes 1
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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
Reservation Options:
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Also Known As:
Chesapeake Beach Hotel Islamorada
Hotel Style:
#4 Top resorts Hotel in Islamorada
#9 On the Beach Hotel in Islamorada

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