Resorts >Chesapeake Resort
83409 Overseas Hwy, Islamorada, FL | Directions 3303624.936497 -80.613545
Mon. - Sun. 24 Hours
Chesapeake Beach is a great resort. This is my 3rd trip to Islamorada and I've stayed at The Hampton Inn before which is also very nice. I would rate Chesapeake above it because it feels more homey and has an old school Keys-feel. We stayed in room 314 which is an upstairs villa with an efficiency. It overlooks the water and a small lagoon. I really think we lucked out with this room. It's quaint and picturesque. I would definitely stay here again. If you're party crazy, I would stay somewhere else. It's more of a family/couples environment.
We had a great stay at the Chesapeake Beach Resort this weekend August 9th through the 12th. The front desk staff (Cesar and a girl) were very helpful and courteous. The stay got even better as we (there were 6 in our party) headed down to the waterfront to catch some sun and enjoy the ocean, hammocks, hotub, and pool. The person in charge of the waterfront activities (Bobby) made our trip that much more enjoyable! Being a sailor, I enjoyed being able to use the hotel's Hobie Wave to sail around behind the hotel and it was free at that. The grounds, and pool area were kept immaculately clean. Aside from the hotels's great amenities and staff the overall location of the hotel is perfect. The hotel is next door to two restaurants and walking distance from Holiday Isle tiki bar. In addition, it's only a few minutes drive to Robbie's marina where we hand fed tarpon and Bud N' Mary's where we rented a 26 foot deck boat. Last but not least there was free breakfast provided at the hotel. Eggs, bacon, sausage, muffins, cereal, bagels, waffles and fruit. Perfect, for getting a quick breakfast in before a day on the water in the sun. Keep up the great work! We will definitely be back!
I booked my stay based on Tripadvisor reviews and was not disappointed! In fact, I found Chesapeake exceeded my expectations. Several posted reviews dissed the cleanliness, condition, and bedding qualities of the rooms, so I arrived with a few hesitations.
Checking in at night I was helped by a friendly front desk person. In fact, I called before I arrived thinking I was lost. She coached me with a few simple directions and I arrived safe and secure. Check in was a breeze. I appreciated a real key on a wristband that wouldn't get lost - 2 sets in fact.
My ocean side king suite was immaculate, the bed and pillows very comfortable, and the furnishings quite nice. This is indeed an 'old Florida' style facility, which is what I prefer. The living area had a sofa and 2 arm chairs, as well as storage furniture and large screen tv. The adjacent dining area had a 30" round table w/ 4 side chairs. Two balcony areas, one off the living, another off the bedroom, had 2 arm chairs with side tables. The housekeeping staff were helpful and friendly, not in your face. I left my 'privacy please' tag on several different days and they didn't bother me, but left clean linens in a bag outside my door.
A real treat was the jacuzzi in the king room just steps from the bed; I thought it would be in the bathroom, but it was a second tub altogether. Wonderful for honeymoon romance I would imagine! Relaxing for me before hitting the bed.
The main pool is large enough to swim laps, no deep end or diving board. I actually liked the shallower depth for standing around and visiting with other guests. Plenty of nice quality chaise loungers, umbrella tables with arm chairs, and a large hot tub in the pool area. I didn't go to the second smaller pool, but others seemed to be enjoying it.
There is a beach, though small, but still exists, and you can wade out into the shallow water to enjoy the ocean. Wear shoes as there is seaweed and some gravely rocks as you enter. Not shelling beaches like Sanibel, but still the same wonderful calm, warm ocean water. Low tide was in the morning and was great to get out into the water. Loungers and hammocks and chairs/tables are located along the property's length by the water.
As for the grounds, they were very nice. Not a 5 star overdone resort property, but small gardens along the pathways between buildings. Plenty of parking even for Labor Day weekend, and room for boats to pull in and dock at the nice small harbor there. Lovely plantings and walkways to the pool, water sports area, tennis court, and covered workout weight equipment spot. Elevators that have been added at some point made getting from the first level parking up to my 3rd level room easy. The view of the ocean is spectacular.
I booked an all day off-shore fishing charter with Captains Parker and Grovier on the Danica Anne. My daughter from Miami visited for 2 days, and went fishing w/ me. We caught a lot of fish and had a nice ride with these two gentlemen. A very pleasant fishing experience. Good for singles, couples, family, or up to 6 friends on their nice large 42' boat that has an enclosed cabin, including an airplane size bathroom 'head'. We fisher ladies appreciate that!
I would return again for sure. A diverse crowd at the pool, with folks from Miami, New York, Ohio, and me from Colorado. If you have a boat, it seems a great place to dock and stay.
Hot breakfast is complimentary and decent fare served in an A/C room on the way to the pool and boat area.
Ice and pop machines near the elevators at each level. Some gifts and things for sale in the Lobby. Closest grocery store is 20-30 minutes or so away, so maybe hit it on the way there to stock up if you are fixing for yourself. There is an ATM at the restaurant/harbor complex just to the north by the dockmaster office.
friends and I stayed here for a weekend wedding. very keys-ish in style, feels welcoming. free decent breakfast buffet, resort fee includes renting of kayaks, water bikes, etc. villa had 2 double bed a pull out couch full kitchen with full fridge. pools, hammocks, outside bar-ish area where you can bring your own drinks and chill... I thought it was a nice place to stay
A fun, relaxing place to stay. It wasn't perfect, but I prefer "real" to the sterile perfection of a Marriott or Hilton. We rented a cabin with my mother-in-law, her sister, and our six-year-old. Plenty of room for everyone. Two pools (relatively small from a resort perspective, but plenty big enough for our mermaid), free sea kayaks, and lots of lounge chairs sitting under palm trees. Really, what more do you need? The beds were very firm, but I liked them. The only weak point I found was the breakfast, which we ate inside in a very cramped and chaotic dining room. (It was too windy to eat outside; the paper plates kept blowing away. If they used real plates and bowls, you could probably manage it, and create less waste in the process.) All in all, I would gladly return. (And while you're in the vicinity, eat at Ma's Fish Camp - great food!).
This resort is only two hours from downtown Fort Lauderdale, so closer if you are travelling from Miami. It is a very clean, beautifully positioned property on the Atlantic side of Islamorada. The rooms were nicely appointed with huge bathrooms, lovely ocean views from the balconies, two pools, a watersport hut, free breakfast buffet daily and right next to a huge marina loaded with fishing charters and a handful of good restaurants. What I loved most is the serenity of this property, how welcoming and friendly the staff were and the rooms were tastefully decorated and complete with mini-fridge, coffee makers, flat screens and not old and smelly like some of the other older properties. It was so lovely and also priced very well. I have stayed in the Keys many times and prefer to stay in Islamorada as it is away from the crazy and expensive Key West, yet close enough to get down there for some shopping and sunsets at Mallory Square. There are several fabulous restaurants close to Cheapeake Beach Resort and many great places to watch the sunsets that make travelling to the Keys so special.
We first stopped at Chesapeake Resort for one night in 1981. We loved it so much we ended up staying for a week using it as our base to explore The Keys. Since then we have returned many times staying for a couple of weeks or more. So much more friendly than a chain hotel. The place has a warmth to it, the staff are very friendly and helpful and there are excellent restaurants within a short distance. It is an ideal place for just a couple of nights or for a longer stay. The family who own the resort go out of their way to make you welcome. We often met other visitors who were regulars and who made an annual trip to Chesapeake Resort. As visiting Brits we have always been well cared for in traditional American style. We stayed in both the villas and in the main rooms and found them very comfortable, clean and well appointed. Shall be back again later this year.
We stayed in room 314 which is an upstairs villa with an efficiency. It overlooks the water and a small lagoon. I really think we lucked out with this room. It's quaint and picturesque. I would definitely stay here again.
This is an awesome hotel with good view to sea access, morning views were amazing and it is a calm and quiet resort. The trees, plants, shades and the locations were well maintained, we stayed for a day while on the way to Key west. We loved the place, breakfast was good, pools and tennis courts were nice. Has a small gym. Best thing in this hotel is the view to morning sunrise and calm sea.
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