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Chesapeake Beach Resort

2.5 of 5 83409 Overseas Highway, P.O. Box 909, Islamorada, FL 33036
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Chesapeake Beach Resort
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398 reviews from our community

Traveler rating
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    59
    32
    30
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114
160
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4
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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Saint Louis, Missouri
Senior Contributor
27 reviews 27 reviews
12 hotel reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed yesterday NEW

Having read some of the reviews I had second thoughts about staying here but I am very glad I didn't let some of the negative reviews influence me to change. We had a perfectly delightful long weekend here. Yes, the rooms are a bit tired looking and there are a number of cosmetic issues. But the place has a wonderful... More 

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milwaukee, wi
Contributor
12 reviews 12 reviews
20 helpful votes 20 helpful votes
4 of 5 stars Reviewed 1 week ago

stayed 5 nights - comfortable room over-looking beach. beds comfortable, rooms clean with small refrigerator. charged each day for adequate continental breakfast, whether you had it or not, and at $18 per person, way over-priced. 2 pools, nice beach area. not very up-scale, but adequate, close to 2 marinas. would probably return, although peak season prices are high ($300 per... More 

Was this review helpful? Yes 2
Dallas, Texas
Reviewer
5 reviews 5 reviews
5 helpful votes 5 helpful votes
4 of 5 stars Reviewed 1 week ago via mobile

our family stayed at the hotel for a great price. The place was clean. They have water sports for free! Breakfast included to get your day started. Not the most modern, but for the cost we were pleasantly surprised. Front desk was friendly. Beautiful sunset location.

Was this review helpful? Yes 1
Atlantis, fl
Reviewer
4 reviews 4 reviews
3 hotel reviews
3 of 5 stars Reviewed 1 week ago

The location was great, right on the ocean. Facilities a little tired and dated. Room OK. Bathroom, BAD. Tub/shower had no grab bars and the tub was slippery. Was concerned about my friend as she was recovering from a broken ankle. Had a nice complimentary breakfast with hot and cold items. Had a nice seating area outside. Service people at... More 

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Oldham, United Kingdom
Senior Reviewer
6 reviews 6 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 2 weeks ago

We drove up from Key West looking to break up the journey back to Fort Lauderdale and came across Islamorada, They have a variety of rooms but we wanted a sea view room and to use the pool, 510 was spacious if a little tired, although I tried my best we only got a 15% walk-up discount although there didnt... More 

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Cape Chin
1 review
2 helpful votes 2 helpful votes
2 of 5 stars Reviewed 2 weeks ago

Stayed here last year in Feb, Hotel a little run down and the pics they show must of been taken when refurbished years ago, We reserved for 2015 and we had to cancel 1 1/2 months before our stay time, There is no SET cancellation fee, or a description explaining a cancellation. The mgmt decides what you pay, No description... More 

Was this review helpful? Yes 2
1 review
3 helpful votes 3 helpful votes
1 of 5 stars Reviewed 4 weeks ago

This place looks good online however they jip you. Instead of getting a premium room which we paid for they put us in a deluxe room. After going and arguing with them they had two different views on what the room was and were very dishonest. The place although it has nice views, doesn't have a bar on the beach... More 

Was this review helpful? Yes 3
Boston, Massachusetts
Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
8 helpful votes 8 helpful votes
3 of 5 stars Reviewed December 18, 2014

Great spot for a weekend almost halfway between Miami & Key West. This is an older facility built probably in the 50's. Room are very dated. Out bathroom door hit the toilet when opened or closed. Most sliding door in the facility were not very easy to slide, bad rollers. Parking is tight. Grounds are very well maintained. Hot Tub... More 

Was this review helpful? Yes 4
Buntingford, United Kingdom
Senior Reviewer
10 reviews 10 reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed December 10, 2014

Have stayed at Chesapeake Beach resort on numerous occasions and keep coming back because ,to me , it is the best value for money in the Keys. My room has always been very clean, well appointed and comfortable. The grounds are clean and pleasant and the staff very helpful. When staying with friends we have rented one of the villas... More 

Was this review helpful? Yes 4
Reviewer
4 reviews 4 reviews
6 helpful votes 6 helpful votes
1 of 5 stars Reviewed December 7, 2014 via mobile

FALSE ADVERTISEMENT. This is my first time to Islamorada and I will never stay at this "resort" again. This is NOT a resort but rather a outdated motel on gravel land with a man made fake beach. The room smelt like must and urine upon arrival and we were informed of an $18 daily fee to utilize old beach equipment.... More 

Was this review helpful? Yes 6
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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
Reservation Options:
TripAdvisor is proud to partner with Booking.com, Expedia, Orbitz, Priceline, Despegar.com, TripOnline SA, Odigeo and Tingo so you can book your Chesapeake Beach Resort reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.
Also Known As:
Chesapeake Beach Hotel Islamorada
Hotel Style:
#4 Top resorts Hotel in Islamorada
#10 On the Beach Hotel in Islamorada

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