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“Some Say "Dated" but I Say "Character"”

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Chesapeake Beach Resort
Ranked #13 of 19 Hotels in Islamorada
Reviewed 22 February 2014

Chesapeake Beach Resort has a fabulous website that invited us to stay at this fun and colorful resort. However, once we arrived, we quickly realized that Chesapeake's heyday has passed by a few decades. But it was great just the same. As long as a place is clean and not gross, I never mind if it has been around for awhile. And you can't beat their little horse-shoe-shaped lagoon with massive palm trees and groomed sand.

We stayed in the 2 bedroom suite with no ocean view, room 301. It as clean and nice, but dark and lacking modern conveniences like, oh, outlets and shelves in the bathroom. There was a full kitchen, really nice colors and décor, and a pull out sofa in addition to the two separate queens. Two flat-screen TVs, tall ceilings, and all the soap-shampoo-goodies. When we first walked into the room, however, someone had left the A/C blowing all day so, no lie, it was about 50 degrees. Now us Rhode Islanders are used to the cold after our freezing winter, but seriously? I want to be sweaty hot at will for $320 a night (just one control on the wall -no modern unit). After being told I was playing with the settings too much and it needed to cycle, and that was why it wasn't warm enough, the maintenance man walked in, said, "Nah, this isn't cold," and moved the thermostat up to max while still in A/C mode. No heat ever kicked on. "Oh, okay. Thanks." I shut it off and opened windows and just dealt with it. At least it was nice to sleep to, but it never really got above 65 or so. But it was yet another place in South Florida that was ridiculously overpriced with very little concern for my family's comfort. When I went to get pool towels at the front desk, the front desk person was trying to check new guests while telling someone else on the phone that she couldn't help them right now (explained why no one picked up when I called about pool towels). "Well, something's got to give!" she said. Um, maybe hire another person during rush? Oh, and while I'm ranting, $18 a day for a "Resort Fee" is laughable.

But I'm being nit-picky. We enjoyed our stay. Chesapeake has a lot of charm, and the views of the ocean were spectacular. Warm breeze in my face, my fam playing on the hammock, pelicans surfing the wind, nice guests. It was great. There are two pools, both nice and warm. Most of the staff were nice and accommodating. The grounds were just as immaculate as the rooms. The morning sunrise was the best, with lots of hot and cold breakfast choices at the free breakfast. No restaurant, but there are many restaurants all around Islamorada.

So overall, I thought the value would be much better at around $200 a night instead of over three, but we had fun and it was nice. I would recommend Chesapeake to other families.

Room Tip: Room 301 has some quirky features, and they tell you that when you book the room. There is no ocean...
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  • Stayed: February 2014, travelled with family
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Thank RhodeTripper
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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384 - 390 of 723 reviews

Reviewed 21 February 2014

If you are looking for peace and quiet. This is it! Just perfect, It is an older hotel, but every thing has been redone. We loved it!!!! The view from our room was stunning. It was exactly what we were looking for. Not children around, and very quiet

Room Tip: They don't have a restaurant or bar. There is one just next door....
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  • Stayed: February 2014, travelled as a couple
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Thank deede99
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 18 February 2014

A nice place to stay while fishing/touring the area.
Room was nice, overlooking tennis court. Grounds are nice. A lot to see and do in the area
I'm planning to go back w the family this Spring and will probably stay here again

  • Stayed: January 2014, travelled solo
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Thank JN487
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 12 February 2014

We checked in early afternoon into a garden view room. This was our home base for a two-day fishing trip, so we weren't looking for an ocean view room. It was clean, functional, close to restaurants and next door to our charter boat's dock. For our purposes it was good value for the money.

Room Tip: Get a room as far away from the road as possible
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  • Stayed: April 2013, travelled with friends
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3  Thank Hansen34112
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 12 February 2014

Chesapeake beach resort was a pleasant surprise. Staff very friendly and service oriented. Sits facing the Atlantic in Islamorada. The water is shallow all over the keys but they have 2 pools here and the use of kayaks, paddle boats, bikes. Lots of good restaurants within a couple of miles to right next door. John Pennykemp coral reef state park is north about 30 min drive. Worth a visit or two. We did their snorkel trip to reef. Even though the boat had 49 people on board, it didn't feel crowded. For the price of $40, it is well worth the trip. Reef is spectacular! We also went back to kayak around the mangroves (awesome). Well organized, well maintained and clean grounds with lots of shaded picnic spots and swimming beaches, though beaches are rocky, water shoes recommended.

Room Tip: Our room included breakfast, but we also had a small kitchenette with stove, full size refrig, micro...
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  • Stayed: February 2014, travelled as a couple
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Thank lrwolk
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 27 January 2014

We arrived early and they let us check in straight away, we had a garden view room, as we were only going to sleep there thats all we wanted, what a mistake, right by the main road so the noise of the traffic was constant, our room 102 was clean but very old and tired, the patio doors didn't fit properly, nor did the main door if they had been sealed better the noise wouldn't have been so bad. The balcony is screened off, (I believe to keep critters out) so we didn't sit out there as it felt very claustrophobic. There were three of us in our room, which is for four people but only ever had two towels and had to keep asking for an extra towel, The Bathroom was very small and had seen better days, the AC unit was above the door which was falling apart and don't know how your meant to adjust it as you would have to be over six foot tall. Breakfast was nothing special and very cramped. we were told the pools were heated but they weren't, I heard the pool man telling another guest they were having problems, but another guest said that was just an excuse!! The grounds of the Hotel and the Marina are nice but thats the only plus point, I'm sure there are much nicer hotels in Islamorada, than The Chesapeake which to me was more of a Motel, and the worst hotel we stayed at on our mini road trip to The Keys and Miami.

Room Tip: Don't pick a Garden view room, and maybe stay somewhere else!!
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  • Stayed: January 2014, travelled with family
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4  Thank Trueam
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 26 January 2014

We love Islamorada and have stayed at a view different places. We were looking for a nice ocean front room, comfortable and close to the restaurants we like in Islamorada. We took a chance on Chesapeake after trying another hotel chain who told us that they coundn't guarantee our reservation for a higher floor ocean front room. Isn't that the point of a reservation ?! At the Chesapeake the reservation staff was very accommodating and we were very pleased to see our third floor room with wonderful ocean view. Our balcony was a great place to relax and watch the offshore parasailing and the sunrise. The grounds are very tropical and meticulously kept. A bonus was the cove and the Tiki hut. The room was spacious with a comfortable King bed. Enjoyed the complimentary sea kayaks and bikes. The staff was very pleasant . We definitely are planning a return trip to the Chesapeake as our resort of choice for Islamorada

  • Stayed: January 2014, travelled as a couple
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1  Thank sunshinegal24
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

Address: 83409 Overseas Hwy, P.O. Box 909, Islamorada, FL 33036-3526
Region: United States > Florida > Florida Keys > Islamorada
Amenities:
Beach Business Centre 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: £165 - £245 (Based on Average Rates for a Standard Room)
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
Chesapeake Beach Resort Islamorada, Florida - Florida Keys

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