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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
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Ranked #15 of 20 Hotels in Islamorada
A recent review
3 of 5 stars reviewed 2 days ago
Eric W Centennial, Colorado
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461 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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Centennial, Colorado
3 of 5 stars Reviewed 2 days ago NEW

Stayed here 3 nights in a 2 bed cottage. Clean but showing its age. Kitchenette was a plus, but we learned the main buiding, without kitchenettes, was newer. Staff was very pleasant. Sunset cruise with Captain Rogers - who runs the Chesapeake sport shack - was easily the best thing we did on the isle! The cruise was worth the... More 

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Boca Raton, Florida
1 review
5 of 5 stars Reviewed 4 days ago NEW

If your lucky to check in here definitely ask for Josh! He is so welcoming and adds to the vacation experience. Great hotel with free water sports and it's all included!! hospitality a + villas a + !!!

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Harrisburg, Pennsylvania
Level Contributor
12 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
4 of 5 stars Reviewed 1 week ago via mobile

Had a lovely time staying here. Two pools , I. The bay side , rooms could be a little more updated but everything was clean, bed was very comfortable , had a refrigerator and balcony overlooking the beach and one of the pools and a waterfall ,the environment is beautifully tropical. We had free continental breakfast every morning outside by... More 

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Level Contributor
4 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We visited here for my mother's birthday and brought our 4 children with us. I was nervous about the party focus for most resorts in the keys. This resort was perfect for us. It focuses on family activities, relaxing nooks, super clean amenities, 2 warm pools to swim even after dark ocean side, water activities like kaiaking, and even a... More 

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Level Contributor
15 reviews
common_n_hotel_reviews_1bd8 4 helpful votes
4 of 5 stars Reviewed 2 weeks ago

The resort isn't luxurious but kept clean. We stayed in a villa which had a kitchen. Our kids stayed in ocean front rooms which look like they have been remodeled. The facility provides an adequate breakfast, kayeks, paddle boats, bikes, a tennis court, and 2 pools with a jacuzzi. The location is fabulous and close to great restaurants and shopping.... More 

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Doral, Florida
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 2 weeks ago

I recently spent the weekend there with my family and had a wonderful time. My five year old had a blast on the paddle boat, as well as the pool. The iguanas roam freely through the property and even pose for you when taking a picture.

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Level Contributor
9 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
4 of 5 stars Reviewed 2 weeks ago

Went during the month of June with our three children ages 5,6, and 13. We had a great room for the 5 days we were there. We had a villa with two full size beds, a pull out bed in the couch and a full kitchen. Everyone was very comfortable during our stay. Breakfast served every morning and you can... More 

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Yulee, Florida
Level Contributor
6 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
4 of 5 stars Reviewed 2 weeks ago

We booked a garden view room with a screened porch, which sounded nice online, a ground floor looking at the tennis courts, but it was hot on porch and old accommodations. I walked around the corner of the building and saw the beautiful rest of the resort, went to the front desk and was given a reduced rate for an... More 

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St. Moritz, Switzerland
Level Contributor
301 reviews
110 hotel reviews
common_n_hotel_reviews_1bd8 338 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We found a good deal and decided on short notice to stay at this resort. Front office staff was friendly and we got an upgrade to their largest two bedroom unit, which was really extremly large and comfortable. Well furnished, however the bedrooms on the darker side - no problem there, it's where you sleep anyway. There was a large... More 

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Toledo, Ohio
Level Contributor
18 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 24 helpful votes
3 of 5 stars Reviewed 3 weeks ago

My husband and I stayed here in May. When we arrived we were told there was only one pool as the other was being worked on. If I would have known this when booking, I would have not stayed here. That was a big draw for me, since when I go on vacation I'd rather not have another guest sitting... More 

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