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All 20 Islamorada hotels

Chesapeake Beach Resort

2.5 of 5 Resort   |   83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Ranked #14 of 20 Hotels in Islamorada
A recent review
5 of 5 stars reviewed yesterday
audieroses Boca Raton , Fl
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367 reviews from our 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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Boca Raton , Fl
Senior Reviewer
9 reviews 9 reviews
5 hotel reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed yesterday NEW

We arrived early on a Sunday Morning about 10:30 AM to Chesapeake Beach Resort. We were greeted by NELSON at the front desk. He was a delight! We were immediately checked in to our Villa 306. Fantastic!!!! We parked in the shade right at the villa ( easy to unload our Children & the car. Great screened in front porch... More

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Pinckney, Michigan
Top Contributor
55 reviews 55 reviews
13 hotel reviews
34 helpful votes 34 helpful votes
2 of 5 stars Reviewed 2 days ago NEW

As my title says I have some good things to say about this resort but sadly some bad things as well. I struggled with only giving this place 2 stars but 3 stars was "Average" and seeing as we were paying $185 a night after resort fee's and taxes I didn't think that average fit what we experienced here. First... More

Was this review helpful? Yes 1
Naples, Florida
Top Contributor
75 reviews 75 reviews
10 hotel reviews
16 helpful votes 16 helpful votes
3 of 5 stars Reviewed 3 days ago NEW

The hotel is located on the ocean and has a beautiful lagoon with slips for small boats. Upon arriving I was assigned a cabin next to the road. The staff was very helpful in assigning me a larger cabin closer to the lagoon. The lagoon has places to fish but is difficult to access if you would like to swim.... More

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Saint Augustine Beach, Florida
Contributor
19 reviews 19 reviews
3 hotel reviews
5 helpful votes 5 helpful votes
2 of 5 stars Reviewed 1 week ago

Disappointment with a capital “D.” After prepaying over $200 a night and then a six-hour drive fighting holiday traffic, we found a compound-type property that is sorely lacking in maintenance. A poorly constructed “bar” on the first floor of the two-story tiki was fallling in, the “exercise area” was a tiny outdoor tiki with two ancient, rusted exercise machines and... More

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ft lauderdale, fl
Senior Contributor
32 reviews 32 reviews
11 hotel reviews
16 helpful votes 16 helpful votes
2 of 5 stars Reviewed 2 weeks ago

We have been coming to the Keys for years and years and never had the opportunity to stay here and have always wanted to. Finally we stayed and we were very disappointed. I will say the front desk staff was very friendly. The property is in dire need of fixing up. The pools were all cracked and needed redoing. The... More

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Reviewer
3 reviews 3 reviews
6 helpful votes 6 helpful votes
1 of 5 stars Reviewed 2 weeks ago

This have been one of the most horrendous experience in a hotel that we have ever had. The rooms were nasty , the sheets dirty! Hair all over! I called the front desk to complain and they sent the gardener w 2 sheets. The bathrooms outdated/dirty . The best part , the "Fitness center" one bicycle and one bench ,... More

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Rotonda, Florida, United States
Senior Contributor
23 reviews 23 reviews
3 hotel reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed 3 weeks ago

We decided to stay the night in Islamarada after a day trip to the keys. Chesapeake Resort had a room available so there we stayed. The resort is showing some wear. (I stayed there once before many years ago) It was clean. That is the most important thing I look for when I stay the night away from home! My... More

Was this review helpful? Yes 1
Harwich, United Kingdom
Senior Contributor
32 reviews 32 reviews
18 hotel reviews
13 helpful votes 13 helpful votes
4 of 5 stars Reviewed 4 weeks ago

After a long drive from Tampa on my way to key west, I just pitched up on a whim. The place was empty after the kids went back to school. Just stayed for a night, but it was a great place to stay. Room was comfortable and cool and well appointed. Facilities were good with 2 swimming pools, tennis courts... More

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Senior Reviewer
10 reviews 10 reviews
3 hotel reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed 4 weeks ago

Once again, the Chesapeake Beach resort has made us ridiculously satisfied. If you're looking for a high-end hotel, keep going. It's a throwback-type motel that you would expect in the 50's or 60's but it really doesn't disappoint. It's quaint and the location is great. Unlike other resorts we've found throughout the Keys, they don't mind you bringing a cooler... More

Was this review helpful? Yes 2
Fort Lauderdale, Florida
Senior Contributor
27 reviews 27 reviews
18 hotel reviews
34 helpful votes 34 helpful votes
4 of 5 stars Reviewed August 24, 2014

My boyfriend and I chose this hotel because we have a 23ft Yamaha and wanted to launch and dock our boat at the hotel where we were staying. Upon arrival, James at the front desk checked us in quickly and our room was ready at 12:00 PM. Upon walking into our garden view room, I was overwhelmed by the smell... More

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Additional Information about Chesapeake Beach Resort

Address: 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
Phone Number:
Location: United States > Florida > Florida Keys > Islamorada
Price Range (Based on Average Rates): $$
Hotel Class:2.5 star — Chesapeake Beach Resort 2.5*
Number of rooms: 65
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Also Known As:
Chesapeake Beach Hotel Islamorada

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