There would be much to say about the Florida Keys in general and the chesapeake resort in particular. Other reviews on various local hotels describe the situation rather well. Refer to them, positive or negative, there is a lot to learn from them.
We stayed three nights at the chesapeake resort and it has nothing to do in glossy paper vacation catalogs of luxury resorts.
If you want to approach some sort of “cosy standard” you’ll need to book one of the ocean front rooms. The garden view rooms are very very “basic”, old and worn out so they can’t even compete with most standard Holiday Inn, Confort Inn, Best Western that you would find anywhere in California, for instance.
The airco is an old noisy (but efficient, in March) unit, good thing that it was not needed at night and that we could sleep with the slide door open. The terrace is equipped with a small mesh net that prevent any mosquitos or flying insects to come in. Positive. It’s not the case for the ocean front rooms and suites. But if you’re a light sleeper beware of the overseas highway noise : you get it through your front door and from your balcony. Something again, that you would avoid by choosing a ocean front room.
There is a free safe in the room and a small refrigerator, both positive. But there is not closet for your clothes, just a tube when you hand them at.
There is no beach (so don’t believe catalogs that would pretend there is) as mostly on the Florida Keys - forget about swimming in the sea - and it’s located on the atlantic side. So also forget about the glorious sunsets if you are an addict of that (we are not). Most hotels, motels and tourist overnight facilities are rather old buildings and often ridiculously overpriced. You really pay a lot for the local site and nature.
The most provocative factor is "breakfast", which is really an open air counter located in a little hut ("SpoonBill café") on the marina. You help yourself to juice, coffee, muffins, rolls, all of them wrapped in a transparent plastic bag (straight from the factory) and not worth very much. Luckily there wa also cereals and (some days) yoghurt. Totally unsatisfying and unacceptable. You stand eating that or you sit at the campground table or you go at the second floor if you find a decent chair (a challenge).
The grounds are not really covered with white or yellow sand but more with the type of industrial “sand” that you use for non tarmac roads. Does not hurt if you wear any type of light shoes.
There are two small swimming pools, one of them being a bit heated. To be forgoten if you’re a “swimmer”, unless there is nobody else and you want to make a lot of turns at each end (I did). The sunbathing area around the pools is something like what you get in most Best Western’s, nothing to do with a caribbean resort in the Dominican Republic for instance. The jacuzzi is OK.
We hardly had a smile at the reception desk during the day (the gentleman on evening duty was much friendlier) although the explanations that we got there were complete and correct.
The sunbeds were OK and although there were not that many, always free at any time, as if not too many people were staying there during the most part of the day but were travelling around (what we mostly did). Forget about umbrellas, but this is common in the US, among other places. There are a few “huts”.
The place has a little marina which is pleasant (you can book a fishing ride there) and a lot of pelicans and other seabirds that you can easily photograph. They are local residents and familiar visitors of the so called “whale harbor” located next door. Parking is free and you get towels.
On the whole, we did not expect very much of our stay at the Chesapeake. All the reviews about Fl. Key hotels had disappointed us (too expensive and too many critiques altogether). So we finally planned a shorter three nights stay over there to allow us more time elsewhere in Florida. Knowing that, we finally made the best out of it, staying not too long at the hotel itself and visiting around. Because of the proximity of nature (you are really on the edge of water, the marina, the pelicans, the palm trees...) the availability of sunbeds, the little expectations that we had, we still had a brief but relaxing and pleasant visit in Islamorada.
If you are not living in the US, be aware the the cost of living is high again, especially in the Florida Keys hotels. High to very high rates in most cases. This one was moderate (so to speak) with 132 EUR per night and per room. If you take the place (nature, location, seaside), the time and what we got for the price into account, maybe you won’t get the impression to have been ripped off. You might also like to check the Hampton Inn, further down the road. Much more modern.
A good advice : be sure to reserve early at local restaurants if you go out for dinner. Waiting time is unbearable if you don’t. And think of the “whale harbor” restaurant located next door even if it would not appear on lists that you receive on the spot.