We were rather nervous as we'd booked this hotel as a package with Virgin Holidays and only read the negative reports after booking.

When we arrived we thought it was all going to be true as they'd got our arrival date wrong and our room that we'd been allocated was in use. But they said they would upgrade us for the night and get it sorted in the morning. My parents were given a similar ocean view room that we had booked originally which was perfect and my husband, son and I were upgraded to a suite with jacuzzi which overlooked the harbour and ocean.

It was absolute heaven!!! The view was stunning, location great, quiet, clean and friendly.... And the next morning they told us we could stay in the suite for the whole two weeks!!

We have stayed in the Keys before so we know that things are a little weather beaten but this exceeded our expectations by a long shot!!

The breakfasts were good and plenty and when we go back to the Keys we will definitely stay at the Chesapeake again.

For the money we were very pleased. My wife and I would definitely stay at Chesapeake Resort again. We didn't want to spend much time in our hotel while at the Keys, so we didn't want to pay higher prices. The carpet showed some old stains. The cleanliness of the bed linens and the bathroom was very good. The grounds are beautiful and tropical including palm trees and coconuts galore. I miss having my continental breakfast on their beach which is a phenomenal way to start your day. Directly next door are some resturants, nice in/out-door bar, and a marina, all of which is a very short walk. Beware the mini-frig in your room, it is wired to an unmarked wall switch, so don't switch it off and wonder whats wrong with it, like I did. Our drive to/from Key West avg'd 85 minutes - depends on traffic and how you drive. Garden Suite rooms like we had are closer to the road so you get some traffic noise, esp the lower number rooms exa:201 or 101, 208 is further away from the road. The ocean view rooms and villas are even further away from the road. Most of the Keys are narrow so most hotels will have road noise issues.
My activity recommendation is to sea kayak from Robbies Marina. Sea kayaks are easy to do and you get close up with the real beauty of the Keys. You can practice on the kayaks at the Chesapeake Resort if you aren't sure you can do it. We took our own excursion from Robbies through the Mangroves and over to the Indian Key Historic Island site. Had a flexible cooler on a two person kayak with lunch and beverages. Robbies Marina 8-5:00 Mon to Sun, various rentals, MM 77.

This review needs a relative frame of reference, for which I'll use "$ cost" to weight my views against expectations.

The location is prefect, food, fishing, nightlife literally 50 meter walk to adjacent buildings or just a short drive away. Location on the Keys themselves is perfect so no problem driving back up to the 'mainland' of Florida itself to visit stuff like the Everglades or go further afield. Conversely, driving down the Key West also easily possible, although slightly vexing when roads are really busy, so set off early to Key West. We also drove to St Petes, stayed over a night, then up to Orlando for a few days, then drive back down from Orlando to Islamorada no real problem as the US roads are so good and drivers so polite (don't think so, try driving in UK for a few days! ha ha)

Hotel staff and locals friendly and no problems on that front. But why, oh, why haven't they bothered 'deep cleaning' the rooms in 20 years? A carpet cleaner could do each room for $50 maybe? Cleaners polite and efficient, they even helped me carry a mountain of clutter to the dumpsters without me asking, so I gave them a $20 tip. However, it's not their job to remove years of grime from carpets or otherwise do intensive cleaning tasks is it? The "standard" rooms smelt lived in and a the carpets were all rather "lived in", so might describe as grubby i.e. you can see clear "dirt tracks" around all the areas people walk on. Not good enough, certainly for the price. I'd be happy for Motel prices, but they try to rip you off with an $18/day resort charge which I refused to pay, and said on the first day I wasn't interested in, but still, it gets added to your bill.

Overall, I was 100% happy with my stay, however, in the context of price, I came away thinking why the managers have let it get so grubby and how easy and cheap it would be to fix up as everything else is fundamentally right about the resort and can't be faulted in any other way. I understand the newer "deluxe" seafront rooms are much better, but simply not worth it in my opinion; I'd opt to stay in the Cheeca Lodge or somewhere better if forced to pay the deluxe room [read standard] room price.

<english humour>
I even spotted somebody hanging around the carpark in a dimly lit corner outside the hotel rooms just sitting in a big pickup truck. They were just sitting there for hours on end. I didn't tackle them directly, as Americans are renowned for letting idiots buy guns and I didn't want to get my head blown off. However, on speaking to the hotel reception they laughed and said that is the 24 hour security guard, and yes, she was well armed!
</english humour>

There was no need for security as the amazing FHP are up and down the road outside all night arresting people and zapping everybody with a speed gun, so if you go, don't speed, not even at 4am when you think the road is empty, it isn't and a cop will be in the shadows every night of the week.

There is loads of stuff to do in the vicinity, but a good car is a must.

Don't be put off by other reviews as the location is good, especially for boat fishermen, but conversly, if you will be put off by a grubby room, go elsewhere. Although the cleaners are very good and do the light cleaning perfectly.

Al.

My boyfriend and I wanted to celebrate my last spring break away from all the Key West crazyness, but close to nightlife, relaxation, good watersports, and beautiful water: all for a good price. So I booked a weekend at the Chesapeake Resort, but before I came to tripadvisor. After reading the stuff here I was terrified to go, and even had a backup hotel in mind just incase the terrible reviews here were true.

They weren't!!!

Anyone who didn't enjoy this resort must not have enjoyed the keys at all! This is the cutest place in Islamorada! The beach/laying out area is wonderful and by far the best on the ocean side, not to mention there are two pools, and hammocks everywhere! There is a resort fee of $18.00 a day, but it is NOT hidden, and it gives you unlimited access to the Hobiecats, Kayaks, Peddle Boats, Tennis, and bottled water, and the Miami Herald was delivered to our door daily.

The staff was super friendly. They upgraded our room to a deluxe with a pool and ocean view for no extra charge and gave us a huge discount on an extra night we added because we loved the place so much!

If you're planning a trip here you should know that the keys are about chilling out, laying out, drinking rum and being low-key! If you want the fine-dining experience of a fancy resort then pay the money and avoid the keys. If you want a chill atmosphere with a friendly staff, an awesome private cove and great food and nightlight at your fingertips, this is the place to stay. We loved it here, it was an awesome price, the extra fee was pennies for the use we got out of the kayaks and hobiecat, and we WILL be back.