Chesapeake Resort

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! more

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 more

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 more

This place is clean, fresh, and the views are beautiful. It is reasonably priced and the staff couldn't be nicer or more helpful. You must check out the tiki hut. The breeze is refreshing the ocean view is calendar picture good. A good book and a glass of something and what a good day. I tried to come up with something to be critical about but... Do watch for the guard iguanas that march up the beech every afternoon. Very cool! more

The Chesapeake Resort was exactly what we needed -- low key, comfortable, great location, friendly staff. We ended up being upgraded from a 1 bedroom ocean view villa to a 2 bedroom ocean view villa. It was huge! 1200 sq. ft. with a full kitchen, dining area, living room and 2 bathrooms. As promised, we had a great view of the ocean and the hotel's lagoon.\r \r The continental breakfast was included and was very generous. The heated pool was wonderful and the hot tub/spa was also great. There is no real swimming beach but we didn't really need it. There are several kayaks you can use for free as well as bicycles and rackets for the tennis court. \r \r We would definitely recommend staying here. more

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. more

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! more

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. \r \r 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.\r \r 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.\r \r 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.\r \r 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.\r \r 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.\r \r 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.\r \r 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!\r \r 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.\r \r Hot breakfast is complimentary and decent fare served in an A/C room on the way to the pool and boat area.\r \r 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. more

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!). more

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. more

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. more

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. more

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. more

Would stay there agin any time more

very good hotel, room is very clean , staff is friendly, nice and quiet , good location,close to restaurants, nice place to relax and enjoy. Views are stunning. I would definitely stay there again. You have to be there to see it. more

We had a wonderful time at the Cheasapeeke resort...the room was clean, the beds were comfortable, shower was great. We loved it. more

nice accommodations, free breakfast and nice staff. more

if you want a true keys atmosphere in a beautiful tropical location with clean rooms and a great staff, then this is it. We rented a pet friendly efficiency for two nights. The room was a little outdated but well kept and clean. I think the regular rooms are more up to date. It had a nice screened in porch too. The kids loved using the kayaks and pedal boats in the ocean and snorkeling right off the beach. The beach is not a sandy beach, but there aren't Real sandy beaches in the keys. The lagoon is usually filled with tropical sea life. We saw parrot fish and lobsters. The hammocks around the property are fantastic for relaxing. more

Clean, friendly, low key. Flip flops and beach attire are acceptable everywhere. The staff was extremely helpful and friendly. more

My family spend a week here most years in the same period.\r We take a suite which is excellent value, with a small kitchen where one can prepare simple meals as required.A fridge is provided for the storage of foods, beer and white wine.\r In the evenings we go out for dinner. There are many good restaurants south bound on US1. All in all Cheasapeak beach resort is an excellent place to stay, with many good restaurants available within a short driving distance. more