Chesapeake Beach Resort

This hotel is in need of a dire face lift. The bedroom area of the hotel was decent– but the bathroom was a whole other story. The toilet seat and the floor look like they’ve been around forever, and no matter how many times you clean them they will never look clean, it was really gross. The breakfast «buffet» was pretty sad, if you can even call it breakfast. Probably will not come back again. I have no idea when the pictures they have online were taken but they are misleading.

As frequenters of the keys, we are more into the quiet and relaxing vibe of Key Largo and Islamorada rather than Key West. For that reason we booked this weekend getaway at Chesapeake Resort. We found a decent deal on Groupon, I did some research — mixed reviews, but it included some features we were looking for, so we risked it.
Arriving friday afternoon, check in was very easy. The lady at the front desk was so pleasant and had us checked in, in no time. She handed us two yellow striped beach towels, these could be exchanged anytime at the front desk, but the two had to be given back at check out (there’s a $ 50 charge if you don’t give them back, and they aren’t worth $ 50 people!) There was a older gentleman with her who then gave us a map of the resort, circled a few important spots, like breakfast area, times it was open 7−10am, kayaking 9 – 5, pools, tennis courts, grills etc. He also gave us a list of local spots to see or eat at. He was so knowledgeable and gave us his honest opinions of where was good to eat, where the locals hang out, where has good views and where the beer is cheap :) We were then off to our room.
The room: basic, 2.5÷5 overall. Furniture was fine, mini fridge was great, flat screen TV on the wall — great. We had two full/​queen sized beds, with crisp white linens — great. The let down was that one of the beds we would find later that night had a sink hole in the middle, which made it pointless to sleep in. Cute little balcony with chairs and side table, perfect for drying out wet clothes or drinking the morning cup of joe. The bathroom was in serious need of updating, but there was no mold, and it had the necessities, above all else it was clean. So the kicker when it came to the room was the AC. There was a «window» AC unit above the door, it was ICE COLD. it made the room ICE COLD, which we wanted, but it was constantly buzzing because there was no seal around the door and the air was just seeping out, making it over work. Because it was constantly churning out this freezing air, it produced puddles at the door entrance and we could hear it dripping all night long. For us this wasn’t a deal breaker because the room stayed cold and we were never there during the day, but I could see for some people this would be major.
The grounds were perfect, the beach area was leveled out every morning, so it looked completely untouched, there was plenty of seating, water views from everywhere except the second pool area. The main pool where people congregated had hot tub and looked directly on to the water. The marina was also a great place to spot manatee and fish, the manatees seemed to like sunbathing in there.
We had a plan before we arrived that we would be doing BBQs, and there were plenty of grills to choose from. We picked the one behind the kayaking hut because it had a large table for prep and we could look out on the water. It was a lot of fun, everyone had coolers, since there is no bar or restaurant on the resort, people brought there own beverages and snacks, the rules are cans and plastic only, no glass bottles which everyone seems to adhere to. They have two large ice machines which can be used to fill the ice buckets from the room, or fill your cooler.
Breakfast was basic, very basic. Filled a hole but honestly, with other great breakfast stops close by, we opted to go to Bitton Bistro instead, it is a vacation after all.
As for activities, there is a $ 18 charge per person which gives you access to kayaks, pedal boats, mini catamaran and the benefit of a life guard. This was an incredible deal considering the cost of excursions and rentals in the area. We had a blast kayaking and petting the manatees. And if you are so inclined to jet ski, there is a rental just next door, you can walk or take the bike rental which is included in the $!8.
Overall this was perfect for us, could the resort do with some improvements, sure; but it met our needs and we got to have fun, sun, good food, and lots of encounters with local wildlife.

We really enjoy this place. The property is beautiful. There are plenty of spots along to hang out and feel like your on a private beach. They have 2 pools and a hot tub. They also have a two story chickee hut to hang out they we turned into a great party spot with our group. The rooms are spacious and comfortable but probably could use updating, especially the bathrooms. The staff was friendly. They don’t serve food or drinks on the property so we bring our own and there are other places within walking distance.

Loved the property and all of the little cozy spots to hang by the water. There is not a restaurant or bar on property so bring a cooler with goodies. The only rule is no glass bottles so solo cups or cans. Will definitely come back again. There are two nice pools, a hot tub and lots of areas to sit at. Paddle boats and kayaking are a part of the room and I saw people doing kite surfing but not sure if that was part of the hotel.

Keys-​y, Quaint and a Touch of Kitchy… the Chesapeake is chock full of charm. Having lived in Key West 20 years ago I’ve seen plenty of resorts so when our family headed down from the mainland for a quick stay in Islamorada recently, we chose the Chesapeake because the photos seemed to embody the older Keys style we prefer.
Good: Our kids loved the kayaks and paddle boats, explored the natural raw beauty in the ocean and lagoon, chased a fat iguana, watched fish & jellyfish. There were plenty of nooks and crannies to lounge in full sun or under a chickee hut, great packed sand walkable areas. Our garden view room was fine, the bathroom was functional, affordable price —- and who can complain about a breakfast with lots of food choices looking out at an unending view of the ocean?
Not so good: The main pool (of 2) was being renovated so some disappointment that it wasn’t open, same with the Jacuzzi. My husband wished there were a tiki bar that served drinks.
Overall, it you want to experience the true essence of the Keys, the Chesapeake delivers that quiet serenity, minus the intermittent drilling at the pool.

While there were a few negative reviews we decided to spend our key vacation here in Islamorada at the Chesapeake beach resort. We were not disappointed! This was a great place. While the resort was full, there were still plenty of places to get some privacy. We were surprised at the amount of children present but again, we could find space if and when needed. Lots of equipment to use (kayaks, paddle boats, bikes). The beach areas had nice lounge chairs and hammocks to use and two pools. There was even a tiki hut you could sit in! One pool was heated that had a hot tub close and another smaller pool that was cooler. Lots of wildlife including some iguanas! The room would be what you’d expect. It was large, with a balcony, a fridge, nice sized TV, and a decent bathroom. The bathroom was roomy, a bit dim, crappy shampoo and bath soap. Buy your own at the close by CVS (which also sells beer). Wouldn’t have realized the free breakfast was as good as it was or I’d have been there everyday! It had scrambled eggs, bacon, sausage patties, bagels and cream cheese, cereal, oatmeal, and loads I didn’t see. The staff was great, you would never see an overflowing trash can or other crap you deal with at other hotels. It is what it is, it’s not the Waldorf Estoria. Plus, you can’t beat the freaking view!!!
You won’t or shouldn’t be disappointed in the Chesapeake beach resort!

The Place is very old and not well kept. No customer service. The rooms on-​line are highly NOT reccomended. I will never come back… it is difficult to open the door of the bathroom because. it hits the …

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 of pledge cleaner. I have severe asthma and couldn’t breath in the room. I attempted to air out the room however, the bugs were rolling in. I went back up to the front desk and asked James if he had any other rooms without the pledge smell. He said that he did not but would do what he could to fix the problem. After receiving approval from his manager Massiel (who is super friendly and accommodating) James took us to a different room that offered a breeze direct from the ocean. He also placed an air purifier in the room for hours in an attempt to remove the pledge smell. James and Massiel’s efforts worked and I was able to breathe for the 2 days we were at the hotel. THANK GOD!
We live in Ft. Lauderdale and have stayed at several hotels in all of the FL Keys. Before coming to the keys, one must keep an open mind to their expectations. The hotels in the keys are not 5 star hotels by any means and are «no frills.» As long as they are clean and free of bed bugs, you are good to go!
The boat ramp is narrow, slippery and lined with coral which made launching and loading the boat quite difficult. The floating boat docks had cleats which were not attached parallel to the dock but rather in a 45 degree angle which caused scratches to the hull of the boat. Not all of the floating docks had fenders on them.
The continental breakfast is fabulous and is from 7 – 10 each day. They serve eggs, bacon, sausage, cereal, muffins and coffee/​juices. We boated 3 miles south down to a very nice restaurant called Lazy Days and it was great!
Overall, the stay at this hotel was nice. The Chesapeake offers great service/​staff, location is awesome, the premise itself is nice and the fact you can dock your boat here is a great convenience. If you or your family have severe allergies/​asthma, be sure to call ahead to have non-​invasive cleaners used during the cleaning process of your room :) Thanks again James & Massiel :) We will definitely be back in the future.

Agree with other reviewers that you just can’t find in the Keys the types of hotels you can find in the upper 48. We stayed for 4 nights during the busiest week in the Keys, last week. We stayed in one of the pet-​allowed rooms with a kitchen (thank you for allowing our dog!). It happened to be the one closest to the road with zero view. That said:
Pros:
— Accommodated our little dog
— Nice cleaning staff
— Nice, friendly families staying at resort. We noticed people happily using the bbq grill and picnic table every night. Shuffleboard was nice entertainment.
— Pool was warm and there was a hot tub
— Tiki hut was cool
— Super fun fishing and watching the fish in the lagoon
— AC worked well and was quiet
— Full sized fridge and freezer in kitchen
Cons:
— TV got maybe 5 channels. We’re talkin Nat Geo and Military channel. No movies to purchase or a DVD player.
— Yes, there still are «resorts» with bedspreads and threadbare sheets. This is one of those. Ick.
— Wifi was anciently slow
— No fan in bathroom.
— Breakfast was… yuck. Never went back after first day.
We will be coming back to Islamorada, but not to Chesapeake. Hopefully we can find another place that allows our dog. We loved La Jolla a few years ago, but they don’t allow dogs.

Spent 4 nights 5 days here over Labor Day weekend to celebrate my husband’s 50^th. We rented villa #302– perfect choice for 5 of us plus 2 unexpected college friends for 1 night. Plenty of room for all. Very clean, awesome location complete with the family of 4 manatees who visited the lagoon on Saturday for a good part of the day. Peacefully shared space with the iguanas. Snorkeled, kayaked, swam, BBQ’d, took advantage of the Tiki Hut just steps from our door, watched amazing sunsets every night. Hosts were very nice (Alan) and housekeeping crew were hilarious. Although this is an older property (once owned by Arthur Godfrey), the rooms are very well maintained. The only reason I can’t give 5 stars is because of the water rats (these are not small rodents) that crawled along the railings on the Tiki hut while we were enjoying the view at night. Another suggestion would be to add hooks throughout the villa for towels or clothes. The master bedroom in this villa does not have a closet. Other than that, fully equipped kitchen, plenty of clean pool towels, nice firm, new mattresses, good linens. Would we go back? ABSOLUTELY! Next time we’ll bring our boat and dock it right outside the door.
Highly recommended.

Nice enough place and pleasant staff. Good location at North end of Islamorada and close to some good eateries. The room I stayed in (Garden View) was clean and had a strong A/​C unit. I stayed here a few years back and wanted to give it another try. I travel in the Keys for business and usually stay in a chain place for the work-​related features. Chesapeake is severely lacking in that respect. The wireless connection was constantly dropping out without staying connected for even a minute. I am NOT exaggerating. There is also a tremendous deficiency in television station selections which was disappointing since there was no additional Olympics viewing. No business channels, either. I know those are all first world pains, but they do factor into my travel decisions. Based on the deficiencies in the basic convenience offerings that are very minimal in cost, I can only give Chesapeake 3 stars. With very little investment in inexpensive technology, this place could easily be 5 stars. Too bad, so sad. Unfortunately for Chesapeake, I cannot foresee me staying here again, especially on a business related trip.

friends and I stayed here for a weekend wedding. very keys-​ish in style, feels welcoming. free decent breakfast buffet, resort fee includes renting of kayaks, water bikes, etc. villa had 2 double bed a pull out couch full kitchen with full fridge. pools, hammocks, outside bar-​ish area where you can bring your own drinks and chill… I thought it was a nice place to stay

A fun, relaxing place to stay. It wasn’t perfect, but I prefer «real» to the sterile perfection of a Marriott or Hilton. We rented a cabin with my mother-​in-​law, her sister, and our six-​year-​old. Plenty of room for everyone. Two pools (relatively small from a resort perspective, but plenty big enough for our mermaid), free sea kayaks, and lots of lounge chairs sitting under palm trees. Really, what more do you need? The beds were very firm, but I liked them. The only weak point I found was the breakfast, which we ate inside in a very cramped and chaotic dining room. (It was too windy to eat outside; the paper plates kept blowing away. If they used real plates and bowls, you could probably manage it, and create less waste in the process.) All in all, I would gladly return. (And while you’re in the vicinity, eat at Ma’s Fish Camp — great food!).

This resort is only two hours from downtown Fort Lauderdale, so closer if you are travelling from Miami. It is a very clean, beautifully positioned property on the Atlantic side of Islamorada. The rooms were nicely appointed with huge bathrooms, lovely ocean views from the balconies, two pools, a watersport hut, free breakfast buffet daily and right next to a huge marina loaded with fishing charters and a handful of good restaurants. What I loved most is the serenity of this property, how welcoming and friendly the staff were and the rooms were tastefully decorated and complete with mini-​fridge, coffee makers, flat screens and not old and smelly like some of the other older properties. It was so lovely and also priced very well. I have stayed in the Keys many times and prefer to stay in Islamorada as it is away from the crazy and expensive Key West, yet close enough to get down there for some shopping and sunsets at Mallory Square. There are several fabulous restaurants close to Cheapeake Beach Resort and many great places to watch the sunsets that make travelling to the Keys so special.

Probably less than meets the eye, but we found it to be very clean and well cared for. The advertised water sports really are non-​existent, and the breakfast is on par with the Comfort Inn on most Interstates. If this place were anywhere else, it would be overpriced. But, it’s the keys and you can get ripped off way worse and have a worse room, so, yes, I’d recommend it

Veteran visitors to the Keys agree that there are no good places to stay unless you want to stay in an upscale Hilton-​type place. But there aren’t Marriotts on every Key, and if you want to stay on Islamorada, this isn’t a bad place. It’s not what you would normally expect from a «resort,» but again, in context it is just as good as any other in the area. True, there may not be «soft and luxurious beds.» Yes, there may not be «an upscale bar and restaurant.» OK, your room may not have «a fully stocked minibar.» But you will find a clean and comfortable place to stay, easy access to all Islamorada has to offer, and a super friendly staff. And when I was there it attracted an international and genial clientele from Connecticut, Maryland, and Brooklyn.