We had a wonderful stay at the Chesapeake Beach Resort and would absolutely stay here again. One of the biggest reasons we chose this resort was that it is pet-friendly, allowing us to bring our dogs along for the trip. Traveling with pets can be challenging, so we really appreciated how welcoming the resort was. The location is perfect. Having Publix directly across the street within walking distance was incredibly convenient for groceries, snacks, and anything else we needed during our stay. There are also several restaurants nearby, making it easy to grab a meal without having to drive far. The complimentary breakfast was excellent each morning. The made-to-order omelets were a highlight and something we looked forward to every day. For boaters, the location is hard to beat. The nearby boat ramps made getting on the water quick and easy, and the beautiful clear waters of the Keys were just minutes away. The resort itself was clean, well-maintained, and offered beautiful ocean views. The pool area was relaxing, and the staff was friendly and accommodating throughout our visit. If you’re looking for a pet-friendly resort in Islamorada with a great location, excellent breakfast, and easy access to boating and local attractions, I highly recommend Chesapeake Beach Resort.

We had such a great stay at Chesapeake Beach Resort! The location is perfect, everything was very clean, and the service was outstanding from start to finish. A special shoutout to Jose in Maintenance. He was so attentive, always had a smile on his face, and was quick to help with anything we needed. It is clear he genuinely cares about the guests and takes pride in his work. Yadira and Vanessa in the front office were also wonderful. They were friendly, responsive, and always happy to help with any questions we had. Another big plus was the covered parking. It was so nice not getting into a car that had been sitting in the hot sun all day. Overall, we had an amazing time and felt very well taken care of during our stay. We would absolutely recommend Chesapeake Beach Resort and are already looking forward to coming back!

We had such a wonderful stay at this resort in Islamorada! Check-in was quick and easy, and the staff was incredibly friendly from the moment we arrived. The continental breakfast was delicious — the omelette station was such a nice touch every morning. The private beach was one of our favorite parts of the stay. It was quiet, calm, and so peaceful. We even did yoga on the beach, and the general manager joined us! She was incredibly sweet, and the yoga instructor was amazing. Our room was always spotless and smelled so fresh and clean every time housekeeping came by. The location was also super convenient with a Publix right down the road. I also really enjoyed the complimentary 2-hour water sports rentals that included bikes, kayaking, and paddle boarding. It was such a fun added perk and a great way to enjoy the beautiful surroundings. Overall, such a relaxing experience and we already look forward to staying here again!

Our stay at Chesapeake Beach Resort was absolutely amazing from start to finish! The check-in process was quick and easy, and every staff member made us feel so welcomed and accommodated throughout our stay. The complimentary breakfast each morning was fresh and delicious. I had a made-to-order omelet with spinach, tomato, and feta cheese that was SO good! A huge thank you to Jose, Kathy, and Dilcia for going above and beyond — they were incredibly kind, attentive, and even brought our food directly to the table with a smile. Their hospitality truly made the experience special. Later, we had lunch and drinks at the bar with Jose Y, and he was fantastic! He made amazing drinks and provided outstanding service the entire time. Everything about this resort exceeded expectations, and we can’t wait to come back!

You absolutely cannot beat the customer service here. We have stayed multiple times, and every single time, we are greeting like family - it feels like coming home. The place would not be the same without Chef Chris! Our 3 kids adore him and all the other staff. The staff simply go above and beyond to make every experience exceptional. Very family friendly resort with beautiful views!

We just wrapped up a stay at Chesapeake Beach Resort for our 29th anniversary, and it turned out to be exactly what we needed. From the moment we booked, Jasmine made the entire process smooth and stress-free. She was professional, attentive, and made sure we got the right room for our family. That level of care carried through the entire stay. The property itself has a relaxed, waterfront feel that’s hard to beat. Waking up to the ocean view and spending time between the pool and beach made the trip feel much longer. It was the perfect balance of quiet and comfortable while still being family-friendly for my wife and kids. What really stood out was the staff. Everyone we came across was welcoming, helpful, and genuinely seemed to care about making sure we had a good experience. That consistency makes a difference. For a short anniversary getaway, it checked all the boxes—easy, relaxing, and memorable. We’ll definitely be back.

My family and I recently stayed at Chesapeake Beach Resort and would rate it a solid 4.5 out of 5 (half stars not available on Google). Overall, we had a wonderful experience. The staff truly made the stay memorable…friendly, attentive, and genuinely welcoming throughout. One of the highlights was the breakfast each morning. Having chefs preparing fresh, made-to-order options was a fantastic touch and really elevated the experience. The resort itself is charming, quaint, and beautifully maintained. The pool and hot tub were excellent - my daughter especially loved spending time there. We also appreciated the thoughtful setup of beach chairs and umbrellas scattered throughout the property, making it easy to relax and enjoy the stunning ocean views from different spots. A couple of small suggestions that could make the experience even better: Adding smart/streaming TVs so guests can log into their own Netflix or streaming accounts—especially helpful for families with kids Offering a small library or game area with books and board games available to borrow would be a great added touch for downtime All in all, a relaxing and enjoyable stay, and we would absolutely consider returning. Thank you for a lovely visit!

We were in awe with this place! From immaculate beach themed lobby when you check in to your room over looking the beach! It can't be beat! Super clean facility! Rooms spot on! Two pools, one salt and one fresh water with a hot tub as well. We enjoyed some beach checkers on the life-size game board as well. What makes this place truly special, and in my opinion, "takes the cake" is the made to order egg breakfast! What a differentiator! Awesome job! ? We will be back!

This place was beautiful! Super clean and updated right on the beach! We would 100% stay here again and will recommend to friends and family. The continental breakfast was way better than we expected! They have a build your own omelette bar! The pools were great and warm, we never had to call housekeeping for more towels. Each day they came when we were out and always kept everything neat in the room for us. My only complaint was one day we arrived to the room after being gone all day to our door cracked open from housekeeping and we don’t know how long our room was wide open for. Thankfully nothing seemed out of place.

I spent three nights in room 211 which is a partial ocean view king room. The rooms are fresh and updated; the large walk-in shower and balcony were my favorite parts. The fridge and microwave came in handy. I wish I had paid extra to have the full ocean view, as my room mainly looked at the heated pool and building next door. It had a slight ocean view from the corner of the balcony. The breakfast is excellent; I enjoyed an omelette each morning from the same friendly gentleman. The clear kayaks are right out front and easy to use. I enjoyed both pools and the hot tub along with the live music Saturday afternoon. I was in a real bind in my last day. Jasmine and Vanessa at the front desk went above and beyond to save the day! I am so so grateful to them! This property has a tremendous staff that understands customer service. They are to be applauded. Also, I highly recommend going out on the Morada Mermaid boat to the sandbar and enjoying their sunset cruise. I did both. It leaves from a marina 7 minutes down the road. It is only $50 a person for the month of January which is a steal. A trip to Islamorada isn’t complete unless you get out on the water. The hotel is next door to two great restaurants, Flagler Station and Wahoo’s. Flagler’s is upscale, and Wahoo’s is casual. I had great experiences at both. I will be back! Thank you again.