Resorts >Chesapeake Resort
83409 Overseas Hwy, Islamorada, FL | Directions 3303624.936497 -80.613545
Mon. - Sun. 24 Hours
We came upon this hotel when we thought we'd run out of luck as 4 othr hotels we had called at were ful. (Turned out to be a holiday weekend!) The room we had was on the 2nd floor and, though it didn't look over the bay, it had a great view over the gardens. It was clean and cool.
As with most hotels in Florida it did not serve evening meals but right next door there was a Brazilian Steak restaurant and a buffet fish restaurant. (We went for the fish one which, though very busy with families, managed to fit us in for a lovely meal.
There were also a couple of swimming pools and tennis courts for the energetic.
Breakfast was served at the hotel and was more than adequate.
Avery pleasant place to stay on our way to Key West.
We stayed here for three nights in early November. We really enjoyed it. The resort is by no means fancy, but it was much nicer than we expected. We stayed in an ocean view room and loved it. There was plenty of space, the view was gorgeous, the room was somewhat updated (although again, nothing fancy), and the pool, hot tub, and breakfast were right downstairs. The property was beautiful and extremely relaxing. Maybe we went at a slow time of year, but it almost felt like we had the resort to ourselves. There are lots of lounge chairs and places to relax away from others. The tennis courts, kayaks, and bikes were very fun and included with the resort fee. The breakfast was nothing special, but very adequate and what we expected. We generally drove to restaurants further down the island, but there are a couple of places right next if you want to walk. We recommend Wahoo's happy hour next door for a cool outdoor bar and view and cheap drinks. Overall, we loved the hotel and Islamorada. It's a very relaxing and beautiful getaway with lots of great restaurants close by. We would be very happy to return.
We love this resort! This was our second stay at the Chesapeake, as it has become our "go-to" place in Islamorada. The polite staff, spotless accommodations and serene surroundings made our vacation even more enjoyable.
I really enjoyed the place. There was nothing unpleasant throughout my 3 night stay. We paid $384 per night for this place 2/08/2013 and shared that with 5 people in the villa. We chose the ocean front view villas too. This is an outstanding deal. Breakfast right on the beach. Free kayak/paddleboat/sailboat rental. The sailboat was a 2 person sailboat.
There is a somewhat famous cat there that waits every morning for one of the staff ladies to give her a bowl of milk. The cat is very old, but has character.
Our family of 4 just came back from an excellent stay in a suite at the Chesapeake. Last year, we stayed in a Lanai room at Hawks Cay Resort but found it very expensive for what was provided. We are so pleased that we found the Chesapeake this year! We appreciated being able to use the kitchen to prepare meals which was very helpful. The full fridge, stove and microwave came in very handy. Our daughters, age 11 and 10, enjoyed the complimentary kayaking, shuffleboard, and the pools were terrific. The tiki hut was also a nice place for our whole family to sit and relax. The lagoon was picturesque and it was great to sit beside during the morning as we enjoyed our complimentary breakfast. This hotel is in a great location and it provided us with great value for our money. We will definitely stay at the Chesapeake again!
The deep sea fishing was as challenging and exciting as everyone has told me. While the tropical nights where romantic and leisurely spent in our clean and well maintained villa over looking the lagoon. With such helpful and courteous staff I could not imagine a better vacation get away.
I am from Toronto, Canada and here at the Chesapeake Beach Resort for two weeks “working”. My room is overlooking the lagoon, there are hammocks between the palm trees, and the views are spectacular. I come every year to recharge my batteries. I love to swim in the lagoon; I have seen manatees and dolphins. I spend many leisurely hours on the point taking pictures, enjoying the sunrise and getting inspiration for my writings. The room is clean; the staff is so friendly and helpful. This is a wonderful place. A # 10 for me. it is a piece of Paradise.
Decided to go to Islamorada for the weekend to surprise my son for his 13th birthday! After reading reviews here on tripadvisor, picked Chesapeake Beach Resort and what a gem. From Overseas Hwy, it looks like a small resort but it opens up on the ocean to a large stretch of hammocks and tiki huts and numerous beach chairs and seating areas, with 2 nice pools. The grounds were very tropical and well kept. We made use of the complimentary kayaks and paddle boats and had a blast! The complimentary breakfast was good, especially when sitting outside while eating enjoying the ocean view. We found a great place to eat right next to Bass Pro Shop called Morada Bay Beach Cafe which I highly reccomend...all outside dining and beautiful sunset views. Also, don't miss going the Robbie's Marina right down the road to feed the tarpon. I think my son went through 8 buckets of fish and had a blast. All in all, a great weekend at a great resort in beautiful Islamorada in the Keys!
This property looks like an old rundown keys hotel from the road but is far from it. The rooms are very clean as is the property. It has all of the amenities and the staff is very friendly and hard working. Do not pass up on the wonderful place. I hate to say too much then too many people will want to stay there and I will not be able to get a room
This was my husband and I's 2nd stay at the Chesapeake. We are locals who live just 45 min. from Islamorada but like to "get out of town" and away from the kids for a weekend alone every now and then. Both times, we have had a room with a view of the ocean. The rooms are spacious and very clean, beds are comfortable. The room has a mini fridge for your adult beverages. I hope the manager is reading this review because the one thing they could really improve on is their service of the morning coffee! Sounds silly, but you are given small cups (seems not much larger than a shot glass) Really, people, give your guests a decent sized cup of coffee! With no Dunkin Donuts nearby or anything similar, you are kind of stuck, unless you go out. The coffee maker in the room is nice but very small (4 c.) We considered taking our own normal sized coffee cup downstairs and filling them up, but they put so little coffee out, you feel funny hogging it all. This is my only suggestion for improvement and I think easy to remedy. Covered parking is especially nice, we never lost our spot and it's nice for keeping your car cool. Didn't spend much time on the beach or pool, as we like shopping and having drinks or lunch at the Lorelei or at Wahoo's next door. I was disappointed with the $18 daily fee, I think this is new, I don't remember this from a year ago. Since we really didn't use the amenities, it seemed a waste of money. We will definitely return
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