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Chesapeake Resort Key Largo

83409 Overseas Highway Islamorada Keys, Islamorada, FL 33036
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Chesapeake Resort Key Largo
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Ranked #18 of 20 Hotels in Islamorada
A recent review
4 of 5 stars Reviewed April 26, 2015
Sandi H wpb, fl
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10 Reviews from our TripAdvisor Community

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Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    4 of 5 stars
  • Rooms
    4 of 5 stars
  • Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    4 of 5 stars
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wpb, fl
Level Contributor
35 reviews
17 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
4 of 5 stars Reviewed April 26, 2015

We love going to the Keys and this was for my husbands birthday. We had never stayed at the Chesapeake and was pleasantly surprised by it. The desk was friendly and helpful, took the time to show us local eating establishments. When we entered our room, a garden view on the second floor, it was heaven, the air had been... More 

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2 reviews
common_n_hotel_reviews_1bd8 9 helpful votes
1 of 5 stars Reviewed December 14, 2014

This hotel is filthy. The room smelled like mold. The carpets were dirty, behind the nightstand and around the baseboards were caked with grime and dust. The chair had food and who knows what else all over it. The AC was permanently blowing stale air into the room. I never let my bare feet touch the ground and slept in... More 

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Travelers are raving about these Islamorada hotels

2 reviews
common_n_hotel_reviews_1bd8 4 helpful votes
4 of 5 stars Reviewed December 5, 2014 via mobile

Very nice hotel ,beautiful sunset two swimming Pools relex sit back and enjoy! Good breakfast outside having a beautiful view. Big rooms nice and clean and big bathroom also balcony view seaside very cool.

Was this review helpful? Yes 1
Fort Lauderdale, Florida
1 review
common_n_hotel_reviews_1bd8 6 helpful votes
1 of 5 stars Reviewed February 17, 2013

Bottom line: terrible service! The manager and owner were extremely rude and not helpful; because of that we will never stay there again. Although the rooms were nicely renovated and the views beautiful, the service cannot make up for it. There are no onsite restaurants/food or bar; except for a continental breakfast (which was nice but limited). There are much... More 

Was this review helpful? Yes 6
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed February 13, 2013 via mobile

If you want to stay in a reasonable place with a good location, this will work. It is NOT fancy and I would say it is old school Keys accommodations. With that said, for the price, we loved it. I would recommend staying in the villas for a little more privacy. Very simple breakfast provided, clean pools, quiet beach area,... More 

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Boca Raton, Florida
Level Contributor
16 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 11 helpful votes
4 of 5 stars Reviewed July 6, 2012

We have stayed here many times because of the location and the convenience of staying with a small dog. You're right on the Atlantic Ocean with its cool breezes even on the hottest days of summer. They have BBQ stations set up if you want to grill your lunch or dinner. All of the best restaurants in Islamorada are just... More 

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Windham, New Hampshire
Level Contributor
11 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed April 23, 2012

My siblings and our spouses (8 total) joined together for a short reunion at the resort just last week, April 2012. We knew of the place from my brother in law so we expected it to be nice. I didn't know just how nice it was going to be. We all had rooms overlooking the ocean, in King suites. The... More 

Was this review helpful? Yes 5
SALEM, MA.
Level Contributor
51 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 23 helpful votes
4 of 5 stars Reviewed April 15, 2012

This resort is not quite a 4 star resort but it is close. A few repairs and upgrades would help it become a 4 star property. If location is important then this is the place to be. They have a beach, palm trees and a beautiful view. Two pools are on the property . They could be modernized. They have... More 

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Chardon, Ohio
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
4 of 5 stars Reviewed February 27, 2012

This is a nice place to stay when visiting Islamorada. I was there with a bunch of girlfriends for a bachlorette party and this Hotel is very relaxing. There are two pools, a private beach and watersports for rent. There were hammocks to relax in on the beach. If you are traveling to Islamorada you should try to stay here.

Was this review helpful? Yes 1
Roswell, Georgia
2 reviews
common_n_hotel_reviews_1bd8 3 helpful votes
4 of 5 stars Reviewed August 10, 2011

I was looking for a place for a small family reunion in the Keys. The resort provided the perfect accommodations, maintained beautifully, in a great location with all the amenities we could use. Our week down there was an absolute treasure, and we believe our family has discovered a hidden jewel. We are going to make it an annual pilgrimage!

Was this review helpful? Yes 2
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