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Chesapeake Beach Resort – reviews, photos

2.5 of 5
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Hotel amenities
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
Ranked #10 of 15 hotels in Islamorada
4.0 of 5 stars 181 Reviews
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181 reviews from our community

    Trip type
Traveller rating
    55
    70
    21
    20
    15
Date Rating
Florida Keys
Contributor
20 reviews 20 reviews
Reviews in 11 cities Reviews in 11 cities
6 helpful votes 6 helpful votes
“Beautiful Pet-Friendly Oceanfront Resort”
5 of 5 stars Reviewed 21 January 2012

We are writing this post from the balcony of this beautiful family-owned resort and taking in a sweeping view of the Atlantic Ocean. This property is not only great for couples and families, it's also a terrific venue for weddings, and special events. Room blocks are available for groups and there's a cool tiki hut area for parties (in fact they're setting up for a small wedding right now) They also have all kinds of water sports right on premises (we're taking out a sunfish this afternoon) as well as a tennis court, two pools and a sportfishing charter. Even though we live in the Keys, we use the Chesapeake as our own little get-away and especially love staying in the waterfront one bedroom suites that have nice bed linens, double balconies, a separate jacuzzi in the bedroom, large living room and kitchen area. The resort also has very cute, pet friendly cottages with Kitchenettes and you can enjoy a hot breakfast every morning in the "Islamorada Room" which serves up scrambled eggs, sausage, cereals, fresh fruit, pastries, yogurt, etc. Assistant manager Debbie Pearson, front desk manager Will and Caser along with the entire housekeeping staff are always so nice and accommodating. They make our stays here all the more enjoyable and are one of the reasons we keep returning to this little piece of paradise. Time to go sailing.....

Room Tip: The waterfront one bedroom suites are the way to go.
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  • Stayed January 2012, travelled with friends
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Fort Myers, Florida
Senior Contributor
23 reviews 23 reviews
Reviews in 9 cities Reviews in 9 cities
9 helpful votes 9 helpful votes
“Absolutely Great Keys Resort”
5 of 5 stars Reviewed 13 January 2012
1
person found this review helpful

Oceanfront property was well taken care of by a very friendly staff. Pools were warm and very clean; included watersport boats and kayaks were in good condition. Atmosphere and grounds were restful and beautiful. We stayed in one of the resort's villas. EVERYTHING at this resort made for a wonderful anniversary for my husband and I. Thank You Chesapeake Beach

Room Tip: Ask for a room facing the ocean
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  • Stayed January 2012, travelled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Islamorada, Florida
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
“beautiful beautiful property for wedding”
5 of 5 stars Reviewed 12 January 2012

I recently had my wedding at chesapeake and it was so beautiful. I received so many compliments on the location and so many friends told me they would definitely be back. The staff at the resort was so accommodating and made me so happy i decided to get married there. Even with last minute changes, they were easy going and extremely helpful through the entire process. Debbie and Thad were great to work with and made our wedding pretty stress free. We cannot thank them enough!

Room Tip: stay away from the efficiencies if you are looking for a nicer room. The efficiency has a kitchen b...
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  • Stayed January 2012, travelled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Ask kaitlynnL about Chesapeake Beach Resort
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
boca raton
1 review
7 helpful votes 7 helpful votes
“Move On”
3 of 5 stars Reviewed 4 January 2012
7
people found this review helpful

Just got back from 4 days/3 nights at Chesapeake:
The Good: The view of the ocean was awesome, I like the free bottles of water in the room, the people were nice. The breakfast was clean. Bacon and sausage were served daily along with eggs that were not fresh, they must have been powdered. Muffins,cereal, juice, coffee was good and the breakfast was maintained well.The view from the breakfast area was beautiful with seating outside. The sandy beach was very hard sand but groomed every morning. Hammocks and lounge chairs were a nice touch. Free wi-fi and free coffee all day in the lobby.
The Bad: Lightbulbs were out in the bathroom, the screen on the patio was ripped. The bathtub/shower needed a major update! The eggs at breakfast were powdered. The shoreline was not groomed and had loads of seaweed and not very welcoming.
Personally I would not return nor recommend. If I had a view of the ocean it may have made the difference.

Room Tip: Definitely get a room with a view of the ocean
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  • Stayed January 2012, travelled with family
    • 3 of 5 stars Value
    • 3 of 5 stars Sleep Quality
    • 3 of 5 stars Cleanliness
    • 3 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
New York City, New York
Reviewer
4 reviews 4 reviews
Reviews in 4 cities Reviews in 4 cities
4 helpful votes 4 helpful votes
“Relaxing and Simple”
4 of 5 stars Reviewed 28 November 2011
2
people found this review helpful

We recently visited CBR for a wedding weekend and everything turned out great. The only downside was the lack of a bar on-site, but they are next door to a great beach bar, so that worked out. The activities during the day are endless and the place is uber-relaxing.

  • Stayed November 2011, travelled with friends
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 3 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
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Additional Information about Chesapeake Beach Resort

83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Price range (per night):* INR11,090 - 16,523

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