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All 15 Islamorada hotels »

Chesapeake Beach Resort

2.5 of 5
83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Hotel amenities
Special offer
15% off room rate
Ranked #9 of 15 hotels in Islamorada
4.0 of 5 stars 153 Reviews
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153 reviews from our community

    Trip type
Traveller rating
    47
    54
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    17
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Date Rating
BuzzzBabes
Florida Keys
Contributor
15 reviews
5 helpful votes
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... More

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Mary Ann C
Fort Myers, Florida
Contributor
17 reviews
5 helpful votes
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 More

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kaitlynnL
Islamorada, Florida
Reviewer
3 reviews
1 helpful vote
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... More

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Godis12me
boca raton
1 review
5 helpful votes
3 of 5 stars Reviewed 4 January 2012
5
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... More

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SmOp10
New York City, New York
Reviewer
4 reviews
4 helpful votes
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. More

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Robin C
New York City, New York
Senior Reviewer
6 reviews
9 helpful votes
4 of 5 stars Reviewed 24 November 2011
2
people found this review helpful

We wanted a last minute relaxing getaway to the Keys, without driving all the way down to Key West. The Chesapeake Beach came through. The property is compact, with the available kayaks and paddle boats being a big plus. The only time we left the hotel during our stay was for dinner, thanks to the great recommendations of the hotel... More

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Leslie M
Florida, Massachusetts
Reviewer
3 reviews
4 of 5 stars Reviewed 9 November 2011

My hotel had changed my room from water view to road w/o telling me so stayed here last minute. Was pleasantly surprised. Older hotels in Fl can have problems but we found none. The room was clean , quiet and colorful. The price was reasonable compared to other hotels and it included breakfast. The surroundings are just as pictured. We... More

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Adrian F
Aberdeen, Scotland
2 reviews
3 helpful votes
1 of 5 stars Reviewed 2 November 2011
3
people found this review helpful

Used Trip Advisor to select this hotel as we were on a fly drive holiday down the Gulf coast to the Keys. Phoned resort to book stay for 3 nights but left after one. This resort is classed as a 4 star with room rates to match, in reality it is at best a 2 star Bed & breakfast. We... More

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MartiHawkins
PortlandMaine
Senior Reviewer
8 reviews
5 helpful votes
5 of 5 stars Reviewed 7 October 2011

We were given a very good price for our 3 day stay compared to other places near by for not as good accommodations. They did explain that all they had was their renovated original hotel but we were very happy with the room, balcony and location. We did have to wait a while to check in, but once being helped... More

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beachatthedoor
Pompano Beach, Florida
Contributor
16 reviews
7 helpful votes
3 of 5 stars Reviewed 7 October 2011
1
person found this review helpful

This hotel is a good stop over in the Keys as it sits in the middle. This also represents the type of hotel it is, in the middle. It's location is good in that it is next door to a marina, Wahoo's, and a Brazilian buffet which makes drinking, eating, and fishing without having to drive, an easy task. The... More

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