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    Chesapeake Beach Resort

    3.4 (96 reviews)
    PriceyHotels
    Open Open 24 hours

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    Paul S.

    I highly recommend this resort! It's not very big, which I loved, and the ocean view rooms were fantastic. There are two pools with plenty of seating and umbrellas. The breakfast is a must, the omelettes were great! The staff were wonderful, the amenities were abundant and easy to access! I haven't felt this relaxed at a resort for quite some time, and enjoyed everything minute of my stay!

    Stoyan H.

    The good: - decent room - self parking The bad: - consistently rude staff (except Anthony) - no one explained about included breakfast or amenities, we found out when we were checking out - no staff available to get paddles for includes rafts - no bar Save your money and go somewhere else...

    Yogurt station
    Erin V.

    This was our first time back here since it was redone. We went for Mother's Day weekend. My family had three rooms, three children and two dogs. We had THE BEST WEEKEND EVER! The rooms and entire resort were immaculate. The sand was groomed daily, the seaweed was cleaned up several times during the morning so the shoreline was clean to enter the water and use the kayaks and paddle boards. My family had the most memorable time during breakfast. Chef Chris made the best fresh custom to order omelettes, waffles and scrambled eggs. The Sunrise room was kept very clean and stacked. I didn't get pictures until it was closed but my family all found something they loved and we enjoyed sitting outside by the water. They have several places to enjoy your meal. Breakfast was included and was the best way to start our day. Chef Chris and his assistant had great music playing and were so friendly and helpful to the children. They really catered to my family and started our day off with positive vibes. There are two pools, see through kayaks, paddle boards, sand chess & checkers, and several cornhole boards to enjoy. We had an ocean view room and it was very spacious and clean. The entire property was so clean and well groomed. All of the staff was so friendly and attentive. They have live music outside that we enjoyed while having a frozen drink at the pool. My step father enjoyed doing the free yoga outside in the beach with a great teacher. This was an awesome trip all around and we can't wait to come back. It's pet friendly and kid friendly but has such a relaxing and fun vibe!

    Marina entrance and beach point

    First time staying here and we vacation to the keys every year. Can't believe I haven't been here. Previously always stayed at the place with the tiki bar but that's another story. The Chesapeake is my new go to place. Staff has to be the best in the keys. Parking with a 30' boat is good to great, winding road through palms but just the right amount of room. Stayed in a villa by the well protected marina and views were amazing. Grounds are well maintained, some magic elf rakes the grounds and collects the sea weed before wake up. Location is central to everything on isla morada. Oh, did mention the staff. Five stars. "Continental breakfast " please, made to order omelets, waffles, yogurt parfaits. Pet friendly to the extreme. Pools were spotless, fresh towels, bartender would bring drinks to poolside. Can't say enough. Will be booking here for the foreseeable future.

    Lorri C.

    We had a great experience here. The staff were very friendly from the front desk, housekeeping and Eric at the bar. A great shout out to the chefs and their awesome omelets (Chris and can't remember the chef that was there on Friday, May 31 2024 and the young lady that hustled around making sure everyone was taken care of. The room was clean, pools refreshing and total access to the beach for swimming, fishing, kayaking and paddle boarding (all equipment was free for 2 hrs). Highly recommend this place for place to stay. Restaurants within walking distance and just an all around great place with awesome staff!

    Here is the more shaded pool. I dubbed this the lush pool. I loved being surrounded by all the plants.

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    10 years ago

    Wonderful little Floridian resort. Property is a little older but clean. Beachfront allows wonderful sun rises. We had a fabulous time.

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    Page 3 of 3

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    Review Highlights - Chesapeake Beach Resort

    Our king ocean view room was even better than the pictures and the room was spotless upon arrival.

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    The Sunset Inn - Front area parking a little tight but doable

    The Sunset Inn

    (34 reviews)

    Sunday night stay- it was nice. Here is what we liked-…read more* Rooms were clean * It appears it has had a recent face lift. * Close to a couple places we wanted to visit- walking distance to Islamorada Brewery and next door to Mangrove Mike's * Cute little pool area- water was quite warm * Mini fridge has some basics in it but priced reasonable, What could of been better: * It has had a facelift but it has the feel of a flipped house. Floor tiles coming unstuck and lifting. Just little things. *Bed wasn't as comfortable as I would if liked - but that can be subjective. Liked it, price was reasonable and we would stay again

    Well known and respected member of the community, the Sunset Inn was an interesting stay…read more Easy with check-in, parking was a breeze, and the unit was accessible to physically challenged. The hotel itself was very clean, and the room looked like it was recently remodeled. The bed had a European style bottom on it where I kept hitting my ankle and toes. The mattress was kind of soft, but the pillows were really nice and comfortable. The bathroom looked rather old, and the shower itself didn't have a door on it. So you risk getting water onto the bathroom on the floor when you're just taking a normal shower. I liked the rear room door which led to the pool area. The pool was a saltwater type and very inviting. This was a major plus for this Inn. Get the towels from the front office and pick a nice spot around the pool. This area really was well done Shopping is a breeze with the Publix grocery store just one mile south. Many great choices for restaurants are all within 2 miles. There are no places to cook inside the unit, but there is a microwave outback in case you wanna warm something. A small refrigerator is provided along with a coffee maker and Keurig coffee pods. Try not to book a room facing the street, as it gets rather noisy at night. Also, foot traffic during was rather loud up until midnight. There is a great value in staying here as the price for rooms are very reasonable. I think I paid $136 for the night. The two women at check-in were very polite and attentive to my needs. Questions were answered, I think I would stay here again if I didn't have a room up against the highway. Be sure to inquire first.

    Cheeca Lodge & Spa - Crispy Rice

    Cheeca Lodge & Spa

    (605 reviews)

    We had a really nice stay at Cheeca Lodge & Spa in Islamorada. The resort is beautiful, peaceful,…read moreand offers so many amenities that you do not really need to leave the property to have a great time. When we arrived, we were welcomed in the lobby with a glass of champagne, which was a lovely touch. I also liked that valet parking is included in the hotel fee. You can simply drop off your car keys, and the staff will park your car for you. Self-parking is also available if you prefer. One of my favorite areas was the fireplace in the front ocean-view area. At night, there was live music, making it a wonderful place to sit, relax, and enjoy the view. The resort has a lot to offer, including oceanfront family pools, an adult relaxation pool, a swimming beach with loungers, kayaks, paddle boards, fishing rods and reels, and a beautiful 525-foot fishing pier for catch-and-release fishing. There is also a 9 hole executive golf course, tennis courts, pickleball courts, sports courts, and beach cruiser bicycles. Families can enjoy the kids' game room and Camp Cheeca, which provide fun activities for children. Adults can relax at the full-service spa, fitness center, sunrise yoga classes, and water aerobics. The resort also offers Wi-Fi, concierge service, in-room coffee and tea, bottled water, EV charging stations, and shuttle service within 2 miles. Some areas of the resort could use a little restoration. For example, the jacuzzi next to the family pool looked like it needed some maintenance. We also noticed a slight seaweed smell near the beach, but this may be normal during the high season and can depend on the weather and ocean conditions. On our first day, we ate at Nikai, the resort's sushi restaurant. Guests can sit outside and enjoy the view, which I really liked. There is also indoor seating, but the restaurant is fairly small. We ordered the Salmon Aburi, Dragon Roll, and Matsuri Roll. The outdoor seating was definitely my favorite because we could enjoy our food and drinks while taking in the beautiful surroundings. Cheeca Lodge has several dining options besides sushi. Atlantic's Edge offers oceanfront dining with beautiful views and serves breakfast, lunch, and dinner. Mia Cucina serves Italian style dishes in a relaxed setting. Tiki Bar and 25South are great places for drinks, snacks, and casual meals. Guests can also visit Morada Bay Beach Café for a relaxed beachside dining experience. Pierre's is another popular nearby restaurant, known for its elegant atmosphere and beautiful waterfront setting. At night, the front ocean view fireplace area with live music is a great place to enjoy a drink after dinner. The combination of the fire, ocean view, and music creates a very relaxing atmosphere. Having so many restaurants and dining choices nearby makes the resort very convenient. You can enjoy sushi, Italian food, casual drinks, beachside meals, or a more elegant dinner without traveling far. The resort has a beautiful Florida Keys atmosphere and offers plenty of activities for both adults and families. I especially liked having so many options in one place, including the beach, pools, water activities, fishing, golf, tennis, pickleball, spa, restaurants, live music, and our comfortable ocean-view room with a fireplace. It is a great place to relax, enjoy the water, dine, and have everything conveniently located at the resort. The champagne welcome, included valet parking, ocean views, fireplace, and live music were also nice extra touches. Although a few areas need a little restoration and there was a slight seaweed smell during the high season, these issues did not ruin our stay. I would definitely recommend Cheeca Lodge & Spa if you are planning a trip to the Florida Keys and want a resort with plenty of amenities, beautiful views, comfortable rooms, great dining options, and a relaxing atmosphere.

    Cheeca Lodge was everything we hoped for and more. We absolutely loved our stay and can't wait to…read morecome back. From the moment we arrived, we felt genuinely welcomed. A special thank you to our concierge, Anne, who was absolutely wonderful. She took the time to recommend family-friendly activities both at the lodge and around Islamorada, and her recommendations made our trip even more memorable. One of the best things about Cheeca Lodge is that there's truly something for everyone. We loved that we could paddleboard, kayak, ride bikes, fish off the iconic pier, relax by one of the three beautiful oceanfront pools, or simply enjoy the incredible views. There's even complimentary golf, which we didn't have time to take advantage of this trip. Our lagoon-view room was beautiful, peaceful, and impeccably maintained. The entire property is stunning, secure with gated entry, and offers complimentary parking throughout your stay. We also had an amazing experience at Mia Cucina, the Italian restaurant on site. The food was excellent, but what really stood out was the staff. The chefs were so kind and welcoming to our kids, making dinner feel extra special. The complimentary 24-hour shuttle was another huge plus, making it easy to explore the area without worrying about driving. There's also a 24-hour convenience store right across the street, which came in handy more than once. Islamorada ended up being the perfect destination for our family. It has such a relaxed, laid-back feel while still offering plenty to do. If you're looking for a luxury resort where you can truly unwind, spend quality time with family, and enjoy exceptional hospitality, Cheeca Lodge is it. Thank you to Anne and the entire Cheeca Lodge team for an unforgettable stay. We can't wait to return!

    Islander Resort - Cabana room

    Islander Resort

    (231 reviews)

    The resort was very welcoming, staff are all gems and definitely will be coming back…read more Great location, a bit of seaweed but it was not affecting the amenities. You have paddle boards, kayaks, bicycles, plus several other activities on site. Coming during school time also makes it even better since no influx of kids will be on the premises. This will definitely allow for a better relax time.

    From the moment we arrived at Islander Resort, we knew we were in for something special. While our…read morefirst night didn't go as planned, what truly stood out was how quickly and genuinely the management team stepped in to make things right the very next day. That level of care and accountability speaks volumes. This resort is truly a slice of paradise, beautiful oceanfront views, gorgeous rooms, bungalows facing the pristine private beach, multiple pools, lush tropical grounds, on-site dining, and endless activities that make it impossible to get bored. Whether you're lounging by the water, enjoying a cocktail at the bar, biking around the property, or just soaking in the peaceful island vibe, there's something for everyone. It's a slow pace ñ, relaxing feel; like you're on your own private island. Although we weren't able to kayak or fully enjoy the beach due to sargassum during our stay, it just gives us the perfect reason to come back and experience it all next time! But what made our stay unforgettable was the PEOPLE. A huge heartfelt thank you for superb customer service and for being such a kind, dog-loving resort family; it meant the world to us traveling with our pup. Angela, Dolce, Vanessa, Josh, William, your love for animals and leadership clearly shines through your incredible team; your attention to detail, warmth, and friendliness elevated our entire experience. Charlene, our incredible server at the Tides; you have a wonderful future ahead, thank you for all the love and attention you poured out to us and Bane! You didn't all just meet our expectations; you exceeded them. We truly could not have asked for a better way to celebrate our special day, and we are already looking forward to coming back. Food for thought; the yellowtail snapper fish sandwich at the Tides was incredible and so was the smash burger. The pina coladas were fantastic too. We weren't a fan of the Drift restaurant although it was pretty; the food at the tides bar was much better; think of elevated Bar food but freshly curated. Most importantly they are dog friendly ( no breed or weight restrictions) ; make sure your dog is well trained. We took our big boy and he felt like a prince with his complimentary Islander Bandana and fire hydrant poop bag dispenser; but he is a quiet boy and well behaved . The resort will not tolerate bad behaved dogs or barkers. So please don't ruin it for the rest of us that have well behaved, big dogs, get banned because others don't know how to control their own four legged children.

    Amara Cay Resort - View of the resort out on the water

    Amara Cay Resort

    (201 reviews)

    This was our second year staying at the Amara Cay, and what an enjoyable experience both times. We…read morewere allowed early check in which is such a nice amenity. Check in was quick, and very friendly with recommendations. Our room was on the second floor again, this time an ocean front and wow - it's worth it. We had the courtyard view last time and it's also a very pretty view - you can't lose. The pool area and bar is so wonderful - very scenic, and the service at the bar is great. They have a great menu for lunch options that they bring out to you. The room was very clean, modern, and spacious. You can request a microwave if you need too! There are bikes, paddle boards, and kayaks for rental for free. Lots of things going on in between the three resorts - we wish we'd had a chance to try the yoga! We will be back for years to come.

    I have been staying at Amara Cay for more than a decade, going back to when it was still a Hampton…read moreInn, and it has always been one of my favorite places in the Florida Keys. Unfortunately, this experience was extremely disappointing. The day before my trip, I came down with a cold and decided not to travel. At the same time, I accidentally dropped my phone in the pool and could not make calls. I immediately used my tablet to email both Booking.com and Amara Cay to cancel my reservation. Despite my efforts, the cancellation was not properly handled. When I finally got a replacement phone and called 24 hours later, I was passed back and forth between Amara Cay and Booking.com with no resolution. I was ultimately charged for both nights as a "no-show." Even more frustrating, according to the stated policy, a no-show should result in a charge for one night, not two. Amara Cay later emailed me twice saying they would look into the matter, but no one ever followed up. After more than ten years of being a loyal guest, I am very disappointed. Unfortunately, this experience has caused me to cross Amara Cay off my list. Based on this experience, I cannot recommend this hotel to others.

    Coral Bay Resort - King bed room, small dinette, kitchen, tv and bathroom

    Coral Bay Resort

    (12 reviews)

    $$

    My husband and I were so impressed with this resort! The…read moregrounds were immaculate. It had a welcoming feel. You can tell that they really take pride in every area of the property, rooms, pool and grounds. What a joy!! It was a fantastic experience where we could forget about work and enjoy each moment. We had room 4 which was a kitchen, dining area, king size bed, and bathroom located near the dock. It was clean, up kept and we enjoyed our entire time there! The bed was comfortable and it had a nice TV. My husband brought fishing tackle so that he could fish from the dock and was extremely happy!! Next time he plans to bring his small boat so that he can dock it there. Upon our arrival we were greeted and checked in quickly and efficiently. Our questions about the area, restaurants, etc. were answered and he said he was only a text away if we had any questions at all. This was impressive to me and I was grateful. The sunsets were gorgeous and we were happy we brought our camera. We did not use the pool or the many hammocks and chairs on the grounds but we're happy they were there. We enjoyed the dock and porch area just outside our room and we are looking forward to coming back next year! This resort does not charge for parking or a resort fee which we appreciated and is located 10 to 15 minutes from a Publix in case you would like to purchase items for the kitchen. CVS is near the Publix too. This is a wonderful old style Florida resort that doesn't nickel and dime you for everything. We already have reservations for next year!

    Everything from check in to leaving was excellent . This is like stepping away from the day to day…read morerush we all live in . The staff was almost unnoticeable and the rooms are clean and well maintained . Of you want a quiet keys vacation this would be the one . We are going back next year hope to see you you there .

    Chesapeake Beach Resort - hotels - Updated September 2026

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