Chesapeake Beach Resort — Hotel in Islamorada

If you're looking for a beachfront gem in the Florida Keys, we would highly recommend staying at the Chesapeake Beach Resort in Islamorada 👌

This resort went thru a massive renovation in 2022 & wowza! They did an excellent job!

Here's a quick 'preview' as to what you can expect when you stay here:

🔸️No parking fee (you will find MOST hotels/ resorts in the Florida Keys WILL charge a parking fee & a resort fee) 🔹️Welcome drink upon arrival 🔸️Breakfast included 🔹️In the lobby, you will find snack items & drinks for sale, board games (free of charge), fishing poles & bait (fee applies), along with small toiletries for sale as well 🔸️$40 resort fee (subject to change) 🔹️All Non- motorized water activities (kayaks & paddleboards) are free for the first 2 hours of use 🔸️Has trailer (boat/jet ski) parking (fee applies): On trailer $50/day, or left on dock in water $100/day (subject to change - call to verify) 🔹️Boat & Jet Ski launch available (only available for guests to utilize) call to verify launching is OK for Jet Ski's; this has been changing fast in the Keys 🔸️Sun Tiki sits onsite for water excursions (we suggest using ReefQuest!) 🔹️2 outdoor pools & 1 jacuzzi tub 🔸️Ice machines on site (located on the 1st floor of each building) 🔸️In-room: iron, iron board, hairdryer, coffee maker, fridge, travel size shampoo/conditioner/lotion, small mending kit 🔹️Sleeper sofa in all Villas, King Rooms, & Deluxe Rooms. Unfortunately, no sleeper sofa exists in the Standard Double or Standard Queen Rooms. 🔸️Nice beach area with first come, first serve beach chairs

We will be back to stay again! We really loved the fact that this property went through a huge renovation in 2022, & it truly shows! Here are a few items we think you would appreciate learning about:

🔹️If we had to suggest a room, we recommend staying in a room or villa with a view of the ocean (for obvious reasons), but specifically because you can catch sunrise right from your balcony! 🔹️As funny as this may sound, we really loved the fact that they had a welcome drink! That is one small piece of feeling "welcome" that most International destinations have done a great job at, but rarely found in the USA. A simple welcome gesture, such as this, really makes you feel like you are on vacation! 🔹️Love that they have thought about the 'little' things, and I am specifically talking about having a few fishing poles & bait on-site (small fee), along with a great selection of snacks & beverages for those late-night snack attacks. I'm also talking about not charging to utilize the kayaks & paddle boards and having a boat launch for guests to utilize! If you have a watercraft, it can be a huge pain in the rear to launch it into the water; also, finding a 'public' launch is nearly impossible! Thankfully, they have one on-site! 🔹️The customer service was excellent! Living in Florida, we run into a lot of onery people, especially when it comes to customer service, and unfortunately, it happens more times than not, especially in the Florida Keys. But to our surprise, whenever we had any questions (because you know I'm thorough & like to confirm everything), they were happy to help! 🔹️Location, location, location! We have traveled to the Florida Keys several times, & 9 out of 10 times, we prefer Islamorada! So when you find a newly renovated hotel that sits directly on the ocean & is incredibly close to several restaurants, stores, & anything else you can think of, we jump! 🔹️ Right next to the resort (virtually the same parking lot), you have access to 3 excellent restaurants & several options for not only fishing charters but also jet skis & other water tour guides (you MUST check out Alligator Reef Lighthouse!!)

🌎 We travel for a living (USA & around the globe) and love to share our experiences both here on Google maps and on our social media pages, too! Follow along our travel...

I am giving 3 stars based on what I paid for this room and the expectations I had from conversations and the website.

The room was recently remodeled and was pretty. The property has 2 pools and a little beach. They offer kayak rentals although we didn't use this. It's conveniently located next to restaurants and a bar and a marina.

When we got to the room, it hadn't been finished being cleaned. There was trash in the bathroom, and the floor had dirty footprints. There's nothing like walking into your room and seeing dirty footprints left behind from someone else. This problem was resolved immediately though with an apology. But it does make you question how well things are being cleaned especially during a pandemic.

The next morning, the shower drain was plugged and was ready to overflow by the end of my shower. Anytime the toilet was flushed or sink turned on, the water pressure went to a few drips for about 2-3 minutes. The shower drain problem was fixed within an hour. However, they left what pulled out of the shower in the trash can instead of changing that bag.

There was no extra toilet paper left in the rooms so it was inconvenient to have to walk to reception to request a roll of toilet paper. I pulled our garbage and there were no garbage bags left in the bottom of the trash can so we had to ask for a garbage bag. I've never stayed anywhere that was so stingy with the "little things" especially when paying that price tag.

The overall design in the room is very poorly thought out. There's no counter space in front of a mirror to do hair, make up, or to put in/take out contacts. The room was very, very damp feeling. You would wake up in the morning feeling damp. We were surprised there was no dehumidifier in the room.

No microwave in the room.

It was also frustrating because I called and asked about construction 1 day before arrival (the day I booked) and was told there was no construction projects going on and it may be dusty but they were in between projects so there would be no distribution from equipment. We were woke up one morning at 630 to a skid steer moving stone around.

They did text every morning to see if it wanted house keeping. We frankly didn't want people in our room so we did decline. But that was a nice feature.

Overall, I'm disappointed with this resort and truly expected better for the price tag. It was disappointing to walk into a dirty bathroom, a shower that was clogged and was frequently cold and low pressure, no extra toilet paper or garbage bags in the trash cans, and being told there would be no disruption from equipment and there was.

I was impressed with the quick responses to fix issues... That was appreciated! But they were still issues that should have...

My wife and I arrived late in the evening due to unforeseen travel issues. Thus, we were not fully aware of the resorts physical and visual configurations. However, the staff, particularly Miss. Q., were extremely helpful. Miss Q. was very instrumental in getting us checked in and settled. As she personally escorted us to villa, her parting words were, "you're gonna love what you see in the morning".

We awoke at 630am to the most beautiful sunrise I've seen in many years. Miss Q. was "right on the money" with her description. We literally watched the sun rise out of the ocean. We sat on the porch of the villa for several hours, only to move inside, open the huge sliding glass door, and sat for several more hours, just watching the water.

The villa is fully equipped with everything you need for a excellent vacation. The king size bed slept like a dream. TV and 5G phone service was just another added bonus. Full size fridge, sink with disposal, and a 2 eye cooktop. Pots, pans, dishes and flatware, tables, chairs, and extremely great views.

The resort is located on a part of the Keys that doesn't have the typical city light pollution aspects. Thus, the evenings are great for star gazing. The views looking up at night were amazing. Again, we sat on the patio just outside the giant sliding glass doors and watched the skies for several hours.

Parking was excellent. As we rented one of the villas, we were able to park our Jeep and trailer adjacent to the villa. We brought our his/hers 3 wheel motorcycles with us. We parked everything snuggled up next to the building. It was all so accommodating.

The resort only has 53 rooms or so. Thus, it is so quite and serene. We could hear the fish jumping out of the water most of the day. The late evening breezes and really cool looking ceiling fans just made for an incredible stay. Restaurants and groceries were all within 1 mile north or south.

Miss Q. and her staff mates checked on us everyday via text. Their messages were very cordial and none intrusive. Did I mention Miss Q. made sure we were checked in properly, as she stayed late to make sure we arrived safely. If you visit the resort, make sure you ask for her. She will defiantly make you stay that much better.

To say we enjoyed our stay is an understatement. My wife was almost in tears upon our departure, as she did not want to leave. We will most assuredly be returning, without hesitation. Villa 311 is our new vacation spot.

Make sure to ask for...