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The Key to Paradise - It’s not often you find a resort that exceeds your wildest dreams. The newly renovated Chesapeake Beach Resort takes everything you’ve ever wanted in a seaside vacation and places it in one scenic, majestic location. Celebrated as the Sport Fishing Capital of the World, Islamorada’s relaxed atmosphere provides an unmatched year-round destination. Visitors flock here for family vacations, group tours, corporate retreats, romantic escapes and more.
Star ratings are intended to indicate the general level of features, amenities, and services to expect. This property is classified according to Giata.
HOTEL STYLE
Centrally Located
Marina View
Languages Spoken
English, Spanish
Location
83409 Overseas Hwy, Islamorada, FL 33036-3526
Chesapeake Beach Resort
241 reviews
Getting there
Somewhat walkable
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Chesapeake Beach Resort is celebrated for its tranquil and picturesque setting, boasting clean, contemporary amenities amidst verdant surroundings. Guests commend the resort for its immaculate and roomy accommodations with stunning vistas, though a few have noted maintenance hiccups. While opinions on value are mixed, many appreciate the diverse breakfast options and complimentary water sports.
The resort's prime location is a highlight, offering easy access to local dining and shopping. Service is generally lauded for its warmth and attentiveness, despite occasional check-in delays.
Location
Convenient
Atmosphere
Tranquil
Rooms
Spacious
Value
Expensive
Cleanliness
Mixed
Service
Inconsistent
Amenities
Satisfactory
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We checked in & were greeted by the nicest staff! Very helpful & gave us good tips for dinner & breakfast. Our room was clean & comfortable with an AMAZING view! I read other reviews about bad views of construction areas & that lead me to choose ocean side. Glad I did. I set on the balcony with coffee & watched the sunrise over the water each morning. Although we did not take advantage of the pools, there were 2 that looked well maintained. The beach area was clean & had plenty loungers. I saw other reviews about not getting their room serviced. We did not have any issues in this regard. They operate on an “as needed” basis using text messages. I liked this way better than someone coming by randomly beating on the door with a shout of “housekeeping!”. We ran out of toilet paper-I sent a text & had toilet paper delivered to the room right away. Each morning we received a text asking if we needing anything & wished us a wonderful day. We will be back to Islamorada & will gladly return to the Chesapeake Beach Resort
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Date of stay: June 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 14 Jun 2021
Thank you for taking the time to share your experience with us and with others. We appreciate your feedback and hope to see you soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Chesepeak is a great new hotel in an awesome location here in islamorada. We come to the keys often however never stayed in islamorada, so we wanted something low key, yet with some nice things to do.
The hotel was purchased in 2017 after it sat vacant for a bit after hurricane Irma. The place was completely gutted and redone due to the damage caused by the storm and by sitting vacant for a time, so everything is new! The rooms are nice, bed comfortable, comes with a mini fridge and a microwave and fairly clean. I did notice little things that could be cleaner such as dust on top of light switch plates, sand or something on the balcony but other then that, it was fine. It's also important to know that the property still has some construction set up, but no active construction going right now. They will be renovating some buildings next to the hotel that will eventually be 1, 2 and 3 bedroom bungalos.
As far ask activities go, the property has 2 pools and a beautiful beach area with plenty of lawn chairs. As far as activities go, you can rent kayaks and a paddle board as well as fishing rods. They also will be adding Jetskis in the near future.
They don't do housekeeping while you stay unless you request it (they text you each morning)
Con wise I would say their: ▪︎the reservation system needs some work ▪︎they can do a better job cleaning up the beach area. There were bottle caps, cigarette butts etc ▪︎need lighting in the overflow parking area ▪︎it would be a good idea to have umbrellas on the beach and at the pool ▪︎no bar or restaurant (it was destroyed during irma)
Overall, I would absolutely stay here again, and I'm looking forward to seeing how this place develops over the course of the year.
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Date of stay: June 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 14 Jun 2021
Thank you for taking the time to share your experience with us and with others. We appreciate your feedback and hope to see you soon!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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This hotel surpassed my expectations. When reading the mixed reviews on Trip Advisor, one needs to evaluate one's own personal priorities. If you're expecting a high-end luxury resort or are looking for an extended stay, you'd best look elsewhere. However, if you're looking for an immaculately clean place with spacious, tastefully decorated, newly remodeled rooms and a beautiful view, this hotel is a solid pick. While the oceanfront rooms are expensive, they are comparable (or less) than other hotels in the Keys. We found most of the staff to be quite helpful and friendly. Shakita, at the front desk, always welcomed us with a smile. Other members of the staff kept things well maintained by raking seaweed from the beach, tending to the landscaping and power-washing the walkways. During our 3-day stay, it never felt crowded. There were plenty of lounge chairs on the beach and space in the pool for all. While fairly close to the highway, it never seemed loud. There was a laid back feel to the place. We liked having a microwave and small fridge in the room, too. It was fun playing corn hole on the beach (there were board games available, too). It's true that you have to sign out your beach towels each day, pay for kayak rentals, and the continental breakfast is average at best (it was good enough for us)...but hey, they were available, and it kept the price in check. We would definitely stay here again.
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Date of stay: April 2023
Value
Location
Service
Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 2 May 2023
Thank you for taking the time to share your experience with us and with others! We are delighted you enjoyed your stay!! We hope to see you again soon!
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At first glance this place is beautiful. The property as far as the beach and pool are very convenient and make the property appealing. We booked this last minute, for two days, and were rarely in our hotel room. Unfortunately, the time that we spent in the room and wanted to sleep.. we heard every movement of the next room over. Every time there phone went off, music was on after midnight, every time someone sneezed, we even knew every time they were taking a shower or having a conversation. It was frustrating, and on top of it we felt like we had to be super quiet and whisper so we didn’t disturb anyone. Our latch on our door did not work properly, and we found that you kind of had to play around with it. We woke up one morning with the door pushed open, and that happened two other times on the trip. Also, the way the shower was set up, when you go to turn it on be prepared to be sprayed with cold water.. there’s no way around it. We had a small balcony that looked into a construction area, but we were able to look past that because we read reviews that they were under construction. The rooms themselves are beautiful and decorated to appeal. We tried to change rooms, but were told that the only room available was on the other side of the room the noise was coming from.. this is mainly due I’m guessing to the paper thin walls. The manager did call me the next day, and offered to refund the $27 resort fee.. I feel like more should be done. But I would say she approached the situation with a lot more concern than the desk girl did initially because she was not professional. After getting back to our room the first night, we tried to find another hotel to stay at but there were no vacancies in the area.. so we were stuck.. I’m going to contact hotels.com that we booked through to see if they could do something. I’ve traveled often and have stayed at a wide variety of hotels (1-star to 5-star) and this is the most unpleasant experience I have had. I do not recommend this hotel, and would recommend staying at the Hadley House that our friends stayed at which is only a mile south from there.
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Date of stay: February 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 3 Mar 2021
Thank you for taking the time to share your experience with us. Your comments have been shared with the team in hopes to prevent any future disappointment. Thanks again and we hope to see you soon.
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My friends and family booked this hotel for 6 days and ended up leaving after one night. People staying here should be advised that the hotel is right off overseas highway and road noise is significant. Garden view rooms are small, lacking storage and have no bathroom storage. The small sandy area outside the balconies is fun for the kids but we found broken glass and cigarette butts. The beach behind the ocean view rooms was also littered with cigarette butts and covered in smelly seaweed. One of the rooms we reserved did appear to have been cleaned and had hair on the sheets under the covers. The floors were not clean and despite having a no smoking policy, smoking was rampant. The resort was kind enough to let us cancel the remainder of our reservation and refund us 50% of our reservation however, we wouldn’t recommend this hotel for those with families as it didn’t seem clean, or family focused.
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Date of stay: March 2021Trip type: Travelled with family
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 28 Apr 2021
Thank you for taking the time to share your experience with us. Your comments have been shared with the team in hopes to prevent any future disappointment. Thanks again and we hope to see you soon.
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Fantastic location for fishing, jet ski and other water activities. The rooms were fairly updated with a few design flaws. The refrigerator and microwave are stored together in an enclosed cabinet, without any ventilation. There was limited storage or countertop space, making it challenging for 3 people to stay organized. The glass shower door made an extremely loud noise when closing. The cubby for the coffee maker should have lighting as the cubby is dark, making it a challenge to make coffee without having to turn on several lights just to see. The walls were thin and you can hear the other rooms conversations. The exterior walkway was filthy! There was stains on the walkway that was either coffee/beverage drippings or trash that had leaked. The trash storage area was right outside rooms and it was clear it hadn’t been mopped in some time. There is a resort fee of $25 per day that covers a boxed breakfast that isn’t refrigerated. The pool deck areas wasn’t clean, there was debris ( chip bags, leaves, water bottles) and iguana feces all over. The pool intake vent's were filled with plant debris, clearly hadn’t been cleaned recently. The deep pool was occupied by guests partying, loud music, glass bottles on the pool deck for a long period time. We were uncomfortable staying and moved to the kiddy pool. Under the right management this could be a nice hotel. It appears they are trying, but just falling short from hitting the mark.
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Date of stay: August 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 22 Aug 2022
Thank you for taking the time to share your experience with us. Your comments have been shared with the team in hopes to prevent any future disappointment.
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Beautiful resort with fantastic views if you’re staying in the ocean view rooms. Construction is going on so the courtyard view rooms are currently just a view of construction. It’s must needed though and will be beautiful when it’s done. Our only complaint is the jacuzzi isn’t open after sundown. They actually put a lock on it. We are all adults here. If we’re paying $500 a night for a hotel room, we want to relax and unwind in the jacuzzi. It’s too hot to get in the jacuzzi during the day and zero opportunity to enjoy it in the evening. The girl at the front desk said something about sea turtles but that just a bs excuse for them to lock up their jacuzzi at night. We live in Key West and are very familiar with sea turtles and they don’t go in jacuzzis. It’s an excuse to not to be able to use the amenities we pay for in a hotel. We have stayed at Cheeca lodge several times and there are no time frames for the jacuzzis as long as we are quiet and respectable adults. Due to this, we won’t be back to Chesapeake Beach Resort. Spending evenings in the jacuzzi is a big deal for us while we’re on vacation. We will head back down to Cheeca lodge or many of the other hotels that don’t put timeframes on the amenities we pay for. If you don’t care about that, Chesapeake is a decent place, great location and pretty views. I would recommend they put horseshoe and/or cornhole out in the sand. They have plenty of space to do so, for the entertainment of their guests.
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Date of stay: March 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 28 Apr 2021
Thank you for taking the time to share your experience with us and with others. Regarding the swimming pool hours, there is a county ordinance that allows swimming pools/Jacuzzi's to be open from dawn to dusk. Thanks again and we hope to see you soon! Best wishes!
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Beware Overpriced Motel with resort prices. We are from Miami and decided ro spend 1 night in the Keys to relax. They are currently under renovation. The check-in lobby is a makeshift room with no appeal or consideration for the guest experience. There is random equipment being stored all around. Seems more like a makeshift storage area with a table for check in. The property is on the waterfront and has a pool with a view. But no restaurant or bar to enjoy in this area. They did do a nice job with the room renovation and very clean. Breakfast is a box with items like sausage and egg sandwich, cereal and fruit etc. You can pick up in lobby or they will charge $3 to deliver to the room. Again, this is not room service it is a box delivered in a plastic bag. But I was literally appalled by my experience on the way out. I had mistakenly thought that check out was at 12 pm. At 11:10 am someone had knocked on my room to let us know we were past check out. I apologized as I had the time wrong but said we would get going. My friend was in the shower when this happened so we were moving as quickly as we can but was preceded to be interrupted two more times. The third time the lady came in the room and would not close the door and I was still changing. Telling us she would have to charge us if we stayed 5 more minutes. To put this in perspective we were out at 11:31 am. All of this for a hotel charged $480 for 1 night !!
Bottomline this is a Motel and had they charged Motel pricing I might have dealt with it. But for $120 more I could have stayed at the Cheeca Lodge (where I have stayed many times) and they truly understand what hospitality means from check -in yo check out. Go up the street and save yourself the disappointment.
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Date of stay: October 2021Trip type: Travelled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 18 Oct 2021
Thank you for taking the time to share your experience with us. Your comments have been shared with the team in hopes to prevent any future disappointment.
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We stayed at the Chesapeake Resort recently and we were very impressed with the new rooms and all of the new amenities after Hurricane Irma. This used to be our favorite place to stay in Islamorada and after all of the renovations we will certainly be back. The two main buildings have been completely renovated and the rooms are very comfy and nice. The entire property is not yet completed but the pool area and lounging area near the water are perfect. The staff is great and the grounds are cleaned every day by the wonderful staff. There is plenty of shade near the water kayaks and paddle boards available for free. There is not a restaurant on the property but you can walk next door for lunch or dinner. There is also a Publix 1/2 mile away.
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Date of stay: July 2021
Rooms
Location
Service
Room Tip:Clean and relaxing ocean front hotel in Islamorada
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 26 Jul 2021
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and thank you for highly recommending our hotel. Thanks again and we hope to see you soon!
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Check in was late at 130am and the lady at the front desk was so kind and went over everything with me. They texted me in the morning to see if I wanted room cleaned and one morning I forgot to fill out a breakfast sheet and they asked me if I wanted breakfast if I was willing to wait a couple minutes, which I appreciated greatly! The property is beautiful and I’m thankful for the wonderful service. Will definitely be back to visit!
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Date of stay: July 2022Trip type: Travelled solo
Room Tip:Parking is tough, I’d definitely get there before 10pm. They should expand on their parking space
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Response from Christena Gilbert, Other at Chesapeake Beach Resort
Responded 18 Jul 2022
Thank you for taking the time to share your experience with us and with others. We are pleased you enjoyed your stay and thank you for highly recommending our hotel. Thanks again and we hope to see you soon!
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Florida City, Florida5 contributions5 helpful votes
The property is still undergoing a renovation. We anticipate the renovation will be completed mid-2022. Our ocean view and garden view rooms are newly renovated. We have 2 pools, a beach, kayak rentals and fishing pole rentals.
There are more places to choose from in the Islamorada area.
PRICE RANGE
$513 - $1,048 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
chesapeake beach hotel islamorada
LOCATION
United StatesFloridaFlorida KeysIslamorada
NUMBER OF ROOMS
65
Prices are provided by our partners, and reflect total costs of the stay, including all taxes and fees known to our partners. Please see our partners for more details.
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