Chesapeake Resort

(305) 664-4662 | View Website

83409 Overseas Hwy, Islamorada, FL | Directions   33036

24.936497 -80.613545

Open Hours

Mon. - Sun. 24 Hours

 
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Payment Methods: American Express, MasterCard, Visa

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Chesapeake Resort
Chesapeake Resort
Chesapeake Resort
Chesapeake Resort

Reviews for Chesapeake Resort

Recommends
2 months ago

We pulled into Islamorada for a surprise fishing trip for our turning-21 son. Chesapeake rep, Will welcomed us back and made sure our room rate reflected all discounts. After fishing all day 20 miles out in the Atlantic, Will suggested we stop back - even after we'd checked out - to wash up. He had towels awaiting. Nice oceanfront hotel with small town friendly service.

Recommends
3 months ago

It was an awesome vacation. We consisted of two adults and two teenagers. I can not say enough about the grounds of the Resort. They were amazing! It's a great location right on the water with plenty to do. There is a restaurant next door and plenty to see and do in the area. The breakfast was good, just enough. The staff was friendly. We are definitely planning on going back in the Fall.

Recommends
3 months ago

I stayed here during a trying time for the locals, Bartenders Bash, but we all loved our stay at the Chesapeake. My wife and I shared a villa with a friend and everything was clean and working properly. 24 hour security patrolling around was good too since we locked our key in the room late one night. You could tell the front desk ppl were uneasy with us staying there, I guess fearing we would be belligerent drunks. Regardless of the nervousness everything went smoothly, we enjoyed the outdoor BBQ area and the hammocks. I would def stay here again.

Recommends
3 months ago

Loved, loved it. All the employees were friendly, extremely helpful...I needed AA batteries, went to the front counter...the lady offered me two batteries. They were so helpful with directions, activity ideas around the keys, etc. Free kayak use, bike use, paddleboats. Right on the ocean. Beautiful ocean breezes and plenty of sunshine. We were here from wed-Monday. Wed. to Friday we felt like we were all by ourselves...then Friday night, a bunch of people came in, but there were a couple weddings going on at the hotel next door, so we figured it was over flow from there. Breakfast was great out on the beach every morning, until the crowd moved in on the weekend, but nothing the hotel could do about that....Saw lots of lizards, up to 4 feet long. They don't bother anyone. Fun and entertaining to watch. One morning a manatee cow and calf showed up in our lagoon. Lots of fish, a few resident crabs. Lots of chairs and little islands to lay out and enjoy the sunshine. A wonderful pool and hot tub. Everything is clean, reminded me of old Florida, but kept in great shape. Every room has a good view. We stayed in one of the villas, wasn't supposed to be an ocean view, but we could see the ocean right out our front door...from our screened porch. Very quiet here, peaceful, great facility, restaurants within walking distance.

Recommends
4 months ago

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.

Recommends
4 months ago

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.

Recommends
4 months ago

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.

Recommends
5 months ago

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.

Recommends
5 months ago

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!

Recommends
5 months ago

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.

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