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“Paradise in need of a makeover!” 3 of 5 bubbles
Review of Chesapeake Beach Resort

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Chesapeake Beach Resort
Ranked #13 of 19 Hotels in Islamorada
Level Contributor
9 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
“Paradise in need of a makeover!”
3 of 5 bubbles Reviewed December 1, 2012

This is such a beautiful location but unfortunately in need of a multimillion dollar renovation. The cost especially in the villas is overpriced considering the lumpy beds and closet sized bathrooms in some.

Room Tip: Be very selective with the villas. Most are very small and dated with tiny bathrooms. The suites i...
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  • Stayed November 2012, traveled with family
    • 3 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 3 of 5 bubbles
      Sleep Quality
    • 3 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Rindy T
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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670 reviews from our community

Traveler rating
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    47
    47
See reviews for
208
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Rating summary
  • Location
    4.5 of 5 bubbles
  • Sleep Quality
    4 of 5 bubbles
  • Rooms
    3.5 of 5 bubbles
  • Service
    4 of 5 bubbles
  • Value
    3.5 of 5 bubbles
  • Cleanliness
    4 of 5 bubbles
Traveler tips help you choose the right room.   Room tips (197)
Date | Rating
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English first
Fort Walton Beach, Florida
Level Contributor
135 reviews
29 hotel reviews
common_n_hotel_reviews_1bd8 86 helpful votes
4 of 5 bubbles Reviewed November 22, 2012 via mobile

I came down with friends for a NASCAR race. We stayed in a bungalow with two bedrooms and a full kitchen. The bungalow was pretty okay and I scratch my head when I look at the pictures from the website versus reality. The grounds were kept up well. They have a tiki bar that doesn't get used, so my buddies and I took over the bar and made a party that turned into a pretty good time. The resort seems to be a great place for couples and families with kids. The heated pool, hot tub, lagoon, and view are a plus.

Stayed November 2012, traveled with friends
Helpful?
1 Thank Thekeithman
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Phoenix, Arizona
Level Contributor
148 reviews
34 hotel reviews
common_n_hotel_reviews_1bd8 134 helpful votes
4 of 5 bubbles Reviewed November 17, 2012

If you are looking for a relaxing time overlooking the ocean and surrounded by beautiful grounds, this is your place. It's not fancy and the rooms are a bit outdated but it's really a lovely place. Make sure you get the ocean front rooms, though! I don't think we would have enjoyed it nearly as much had we not had the balcony with the view. Breakfast is included and it was nice to grab a bit and sit outside near the water. There's a pool and jacuzzi on property and they were never crowded when we were there. It is walking distance to a couple of great restaurants...one of which provides "room service" through an agreement with the hotel.

Room Tip: Ocean front all the way!
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  • Stayed November 2012, traveled with friends
    • 4 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 4 of 5 bubbles
      Rooms
    • 4 of 5 bubbles
      Cleanliness
    • 4 of 5 bubbles
      Service
Helpful?
Thank azhootie
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Connecticut
Level Contributor
154 reviews
12 hotel reviews
common_n_hotel_reviews_1bd8 59 helpful votes
4 of 5 bubbles Reviewed November 12, 2012

a good way to describe this place is like a " beach compound." its snuggled nicely within its property boundaries and even though your near the road and the neighbors on the sides, you wouldn't know it. pretty large beach area with large tiki hut where you can use the kayaks and paddleboats, also a small marina where you can stroll and watch the boats and talk to the captains and see the catch of the day. beautiful view of the sunrise and plenty of lounge chairs to sit by the water and relax or enjoy a cold beverage. also a nice pool, hot tub and respectable breakfast spread in the morning. eggs, bacon, toast, muffins, coffee, juice, fresh fruit and friendly staff. rooms were clean and room service comes from the restaurant next door called "wahoo's" and was fast and although not cheap, was very good food. no complaints!

  • Stayed November 2012, traveled with family
    • 3 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 4 of 5 bubbles
      Rooms
    • 4 of 5 bubbles
      Cleanliness
    • 4 of 5 bubbles
      Service
Helpful?
1 Thank beachbum393
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Columbia City, Indiana
Level Contributor
25 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
4 of 5 bubbles Reviewed November 6, 2012

My wife and recently stayed at the Chesapeake Beach Resort on Islamorada for 3 days following a business conference in Miami. It's an older, smaller hotel with a bit of wear and tear, but overall a great value. The rooms were clean, breakfast was good, and the staff very friendly and helpful. The beds in our room were a bit on the hard side, but I slept well. The setting on the Atlantic side was beautiful, uncrowded, quiet and relaxing. I spent the better part of one afternoon reading and snoozing in a hammock about 30 feet from the shore. Just what we needed after being in Miami for several days. Plenty of good, close restaurants, including several with beautiful sunset views. Key West was approx. 1.5 - 2 hour drive away. We would definately go back.

  • Stayed November 2012, traveled as a couple
    • 4 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 3 of 5 bubbles
      Sleep Quality
    • 3 of 5 bubbles
      Rooms
    • 4 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Kevin R
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Toronto, Canada
Level Contributor
12 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed November 3, 2012

I am from Toronto, Canada and here at the Chesapeake Beach Resort for two weeks “working”. My room is overlooking the lagoon, there are hammocks between the palm trees, and the views are spectacular. I come every year to recharge my batteries. I love to swim in the lagoon; I have seen manatees and dolphins. I spend many leisurely hours on the point taking pictures, enjoying the sunrise and getting inspiration for my writings. The room is clean; the staff is so friendly and helpful. This is a wonderful place. A # 10 for me. it is a piece of Paradise.

  • Stayed November 2012, traveled solo
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
2 Thank birgittemelnick
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Andover, New Jersey
Level Contributor
15 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed November 2, 2012

I can't think of anything but excellent to say about this resort! The staff was friendly, rooms wer'e spotless and very comfortable. My husband and I make a trip to the keys several times a year for the last eight years wev'e stayed at alot of places. This is now are favorite place to stay! Book a room here and you won't regret it !!!! FANTASTIC.

Room Tip: We had a suite it was waterfront view excellent.
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  • Stayed August 2012, traveled as a couple
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
1 Thank Suzette W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about Chesapeake Beach Resort

Property: Chesapeake Beach Resort
Address: 83409 Overseas Hwy, P.O. Box 909, Islamorada, FL 33036-3526
Location: United States > Florida > Florida Keys > Islamorada
Amenities:
Beach Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Kitchenette Room Service Suites Swimming Pool Wheelchair access
Hotel Style:
#6 Top resorts Hotel in Islamorada
#11 On the Beach Hotel in Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
Number of rooms: 65
Official Description (provided by the hotel):
Islamorada's famous beach and fishing destination, Chesapeake Beach Resort, rests on 6.5 Acres of oceanfront sands and gardens halfway between Miami and Key West, in the Florida Keys. Our property delivers state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer HDTV, Stereo radio/CD/alarm and wireless internet connection, along with carpeting, furniture, bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. ... more   less 
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Also Known As:
Chesapeake Beach Hotel Islamorada

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