This hotel was wonderful. Located right in front of the beach. It appears that all the rooms have great views of the beach. The staff is welcoming and accommodating. Our room was clean and spacious with a small balcony (not private) with the ocean view. The bathroom too, was big. The shower was roomy with proper water pressure. For breakfast, they have your regular continental breakfast along with an omelette bar. Totally unexpected. I thought that was a very nice touch. They have 2 swimming pools: one fresh and the other saltwater. read more

Chesapeake Beach Resort - Hotels Near Me - Islamorada, Florida

The breakfast options are amazing. The views are incredible. The staff was very attentive to our needs. The rooms were clean. We enjoyed the peace and quiet during the week. As we got closer to the holiday weekend, more guests showed up leading to more noise, but that was the only minor issue. The free bikes for 2 hours were really great too. read more

Chesapeake Beach Resort - Pool area - Hotels Near Me - Islamorada, Florida

We called the hotel and booked a one bedroom king suite with a pull out couch for 575$. When we arrived, it was a tiny room with a king bed and a pull out couch that was at the foot of the king bed, not typical industry verbiage indicative of a one bedroom suite. The pull out wasn't ready even though we requested a third party bed. I called front desk and there was an excuse for all my issues, I was told that I could talk to the manager in the morning. We just left. read more

Five night stay from late March-early April. We are already talking about coming back. The staff went out of their way to make us feel like we were on a vacation. Free omelettes in the morning was a wonderful way to begin recovering from the previous day's festivities. The view from our balcony was tremendous. A fabulous place to stay in the Keys if you want some space from the non-stop party of Key West. read more

My wife and I had reservations for a two-night stay March 23. Unfortunately, my mother passed away a few days before that, necessitating that we cancel; I called on March 20 to inform the resort. Despite my prior notification, though, Chesapeake informed Booking.com that we were "no-shows." (I provided Booking with a true account of what happened). Only after repeated calls and emails over the course of the next week by us and Booking.com did the resort authorize Booking to give us a refund but it was a partial one of $527 out of $944. I asked Chesapeake out of common decency due to our family tragedy to give us the rest of our deposit, $417. They declined. read more

The best thing about this place is extremely helpful and friendly staff! Second good thing is the view from ocean front room, the little private Bay Area and the beach. The breakfast is adequate. They do make omelettes as you would like them . That's about it , I'm afraid. The first night we stayed at one of the villas by the road and had no sleep due to the traffic noise on the road. The shower door was stuck and the beds were uncomfortable and noisy. The staff moved us graciously to a waterfront suite. We had to do with queen beds instead of queen and king but the noise now was replaced with the air condition unit which apparently had a mind of its own as we turned it off and it was still making noise. The facilities are definitely overpriced. If you do end up going there do not stay by the road. read more

Solid 3 star motel and resort ( 4.5 star for the Keys). It has pool and very nice pool by the water. It has a very small beach and lagoon. Staff is a great. For the price it is a very nice to stay in the Keys. Room was clean and comfortable. Beds were comfortable but our shower did not work well. Breakfast was great ( free with room). read more

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! read more

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Great spot. Clean room with beautiful bay view. Help was friendly and breakfast excellent. Close walk to decent restaurant. Padded lounge chairs would elevate the experience. read more

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! read more

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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. read more

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My friends and I stayed at the Chesapeake Beach Resort for three nights at the end of October. I opted for a non-view room and will not make that mistake again. It's worth it for the ocean view rooms, which really do have a lovely expanse out to the Atlantic Ocean and small, but nice balconies. My building looked out at a "garden" which was fine, but didn't feel nearly as tropical as it could have...and that's all on me. The room size was great, and everything was very clean. But the walls are paper thin and I could hear kids to one side of me screaming into the night and a person snoring all night to the other side of me. There also isn't any dresser or drawer space...just a small "closet" area with four hangers, which doesn't seem like enough space for a room that should sleep four people. The service was really good, and the team working at the front desk and for maintenance and housekeeping were all incredibly friendly. There isn't daily housekeeping service unless you ask for it. I did request more toiletries and a hair dryer, which were brought when requested, but I also had to ask them to empty the garbage cans. I really do like having the bed made every day and the garbage collected every day when I'm on vacation. Another lesson learned. There are two pools, and a hot tub, as well as beach area and lots of lounge chairs. The pools were chilly so most people used the hot tub as a pool...there were LOTS of children in the hot tub. It would be nice if they had an adult area specifically. Overall, I'd probably stay somewhere else next time. read more

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... read more

Chesapeake Beach Resort - Hotels Near Me - Islamorada, Florida

My husband and I stayed here for our honeymoon in April and this was by far the best place we could have picked! We were happily greeted at check in, room was spotless and cleaned daily, attentive staff who were always nice and helpful, and amazing breakfast each morning. We loved the beautiful view off our balcony and appreciated the well kept grounds. We cannot wait to return!! read more

Quiet. Peaceful. Perfect getaway for couples. Excellent customer service. This was our second stay at Chesapeake. Chesapeake and Islamorada are our new favorite destinations in the Keys. Islamorada reminds us of the Key West we fell in love with 30 years ago. Low key and peaceful. Every day is perfect when starting with Krystal's French toast. Her smile is infectious. She and the breakfast gang aim to please with their attention to detail. The private beach is lovely with shade and sun options. No talking or music. It was the perfect spot to watch the boats at the sand bar or to take a nap. Walk through the adjacent parking lot to four restaurants. We love the casual vibe outside at Wahoos. We can't wait to go back. read more

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! read more

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Beautiful place. No respect for quiet time. Loud music at 0630 in the morning On jet skis right by the rooms as they were unloading themselves in the water. read more

we've been here 2 hours and they don't have glasses for wine or cocktails! they want to sell you some plastic crap ! tell me one hotel that won't or can't supply you with something that's important on a mini vacation read more

Location: convenient Customer service: good Room: clean and looks comfy Beds: not comfy, loud, pillows flat A.C .. we couldn't get it cold enough so we were hot at night. We were delivered the wrong breakfast. When I told them they said they didn't have our breakfast sheet. The lady was kind and made up the boxes for us. Whatever breakfast we were given was for the room upstairs. Before 10 the cleaning lady opened our door and said she was told we had checked out ‍ Beaches :( read more

Clean, comfortable room. The robes were a nice touch. Breakfast was wonderful and plenty of seating with ocean views. Staff lovely as well. read more

Let's start with the price tag: It averaged out to $315 per night... but wait, there's more! Add a $50 per night "amenities fee" for amenities that, as it turns out, are more mythical than a Florida panther. Welcome to the Chesapeake Beach Resort, where the "luxury" is as elusive as Bigfoot. The Welcome Drink That Never Was: We were supposed to be greeted with a complimentary drink upon arrival. Four days later, I'm still parched. The Phantom Amenities: Kayaks, paddleboards, and pedal boats? Good luck finding someone to assist you with them. When we did, they told us it was too windy. Apparently, the kayaks were more scared of the wind than we were. Pool towels? Hope you like reusing, because once you get one, you're married to it for your entire stay -- clean pool towels were as elusive as the amenities. Morning Wake-Up Calls: If you enjoy sleeping in, forget it. The cleaning staff has a different plan. They'll try to bust in before 9:30a and, if that fails, expect a wake-up text. Irony alert: Do Not Disturb signs mean "We'll disturb you via text instead." Thirst Traps: No bar in sight, anywhere. They have canned drinks in a room that's never open or you can go beg for one at the front desk. Water? Bring your own or prepare to spend a small fortune on bottled water. I'm pretty sure we're now majority shareholders in Evian. Food Fiasco: Breakfast is your only option here -- dry cereal, basic omelets, coffee, and tea. No restaurants, no poolside bar, no snacks. They've really perfected the art of the hangry vacationer. The Beach Area - A Bit of a Mirage: Yes, there's giant chess, checkers, and cornhole, which is fun until you realize you can't actually enjoy the ocean. It's basically a sea of turtle grass, so no frolicking in the waves here. Saturday Night Fever (and not in a good way): The sandbar party next door turned the resort into a bass-thumping nightmare. The walls were vibrating, and not in a soothing way. Meanwhile, the pool area became a no-go zone thanks to a family blasting their own distasteful music. Management was MIA. The Staff: Shoutout to Emily and Lisa, the real MVPs of this place! They work their tails off with smiles on their faces despite being overworked and under-supported. They deserve a vacation more than we do. TL; DR? The verdict is in! The property is nice and clean, but that's where the positives end. For what we paid, this experience was a major letdown. I'd recommend saving your money and your sanity -- this is one trip we won't be repeating. read more

My husband & I stayed 3 nights & had a wonderful time. Our room was clean upon arrival. We chose not to have our room cleaned during our stay and enjoyed the hands off approach. You get a 2 hour complimentary rental & they have 2 clear kayaks, stand up paddle boards & non-clear kayaks as well as paddle boats to choose from. The activities attendant is darling and beams positivity! She is friendly, helpful and loves her job. All the staff my husband & I interacted with were accommodating. We had a wonderful baby moon at Chesapeake! read more

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Front desk clerk is very rude and nor the beach or pool have umbrellas. So be ready to get sunburned. read more

When just needing a last minute place to stay, this place will do. It's clean, well maintained, has a small private beach and 2 swimming pools. One of my favorite things to do at night in the keys is to grab a drink and sit out back watching the water...unfortunately this was not as enjoyable as I hoped as there wasn't much light out back. They have plenty of opportunities for nice string lights between the palm trees which would add such a nice ambiance. Again, it's clean, affordable and convenient location if you're in town....just think there is room for improvement. read more

We had an absolutely amazing experience! Check in was at 4pm, but the front desk (who were extremely informative, welcoming and friendly) accommodated a 10:30am check in free of charge. We stayed in a king room with an ocean view - the room itself was renovated (shiny and new!) and we had a view of both the ocean and the pool. The resort itself is the epitome of serenity - it was extremely quiet and peaceful, which was exactly what we were looking for in our weekend getaway. The private beach was a game changer - perfect place to lay out a great backdrop for pictures. They have 2 pools and a jacuzzi as well. There aren't any bars or restaurants on site, but there are literally both next door, just a few steps away. I would 100% recommend this resort and will definitely be booking again in the future. One note - there is renovation still going on, but we didn't experience any disruptive noise during our stay. Can't wait to see what this place looks like after the reno! read more

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The only reason I gave a one is because there wasn't a zero. 4 o'clock checkin is a joke. No, your room isn't ready. Can you tell me when it will be ready? No Front desk couldn't care less. As we waited and waited others came in, complaining about the same thing. Same response. Are you at least discounting the rate? No. Avoid this place like the plague unless you really don't need your room before dark. read more

Stayed here for 3 days 7/3/22. The room was cleaned and has been renovated. Nothing fancy but nice place to stay. Our room small fridge did not work (warm). The toilet handle fell off, and I just screwed it back myself. Adjacent beach was not swimmable due to sea grass. We did not use the two pools on the property. Nice view of the beach. Staffs were friendly depending on who was working and time of day? Included Grab n Go breakfast, but must text or fill out order form before each night. Free Coffee are available around the clock in the lobby. read more

Chesapeake Beach Resort - Hotels Near Me - Islamorada, Florida

Overall nice place. Currently under renovations so kinda look messy but what construction look clean right? The view would've been OUTSTANDING had we not have that big ass tree in front of out balcony. Still can see around it but would've been great to have full view of the ocean and the beach. That and the slight flooding at the entrance (due to raining past day and a half) are my only complaints. Would stay here again, I bet would look nice once all reno is completed and the beach area would be great. read more

The check-in process was seamless, they even provided restaurant recommendations. Location is excellent, with many restaurants nearby. The resort area was pretty spectacular, with the pool and chairs looking at the ocean, tall palm trees creating a nice ambiance, and even a small area where one can safely get into the water. There was a welcome text and I could actually reply to a person and make requests via text. Felt very personalized. read more

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I started my morning with a delicious Omelette from Nari and sat seaside to open up the day. The flavor of the omelette with scent of the sea, perfect. The resort offers beautiful views of the ocean that words can't describe coming from the Midwest, you have TJ experience it read more

Really impressed. We got a king ocean view room and it was basically a one bedroom apartment. The bed was comfy, the bathroom huge (double sink), large shower, huge living room area, two TVs, refrigerator and microwave. Two A/Cs. Two ceiling fans. The staff was very accommodating. Glass of Champagne upon arrival. Nice touch! :) Balcony with chairs and a small table. Two sliding glass doors with a view of the ocean. This hotel uses text messages to communicate about housekeeping needs, and this is a policy I wish every hotel would use. I asked for a high floor weeks before our stay and got not only that, but a corner room with even larger balcony. (Thanks again!) Everything was clean upon arrival. Lots of free parking. Mini store for munchies, drinks, toiletries in the lobby. And they give you a free breakfast everyday. Fresh fruit, water/OJ, microwaveable egg sandwiches, coffee is always available, plus you have a coffee maker in your room. One tiny caveat. There is covered parking in some areas. And while that's very nice, the cement poles near the stairways make it treacherous to get in and out of a space. Nothing to be done about that of course, but it might be better to just park in an outside space. Will return if we get down here again. Keep up the great work guys! read more

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We stayed here for 5 days and 4 nights during the month of October. Great service, great quality rooms and furniture. The beach is not the greatest for swimming but the kayaking was great. We kayaked out to the sandbar, about a mile into the ocean. We spent half a day out at the sandbar and it was great. The resort provided the kayaks. The pools are great and very clean. Walking distance from a good restaurant, Wahoo. Walking distance from a Publix, an excellent grocery store. I would highly recommend the Chesapeake Beach Resort, you just ask and they deliver. read more

Ok this is my version on my personal experience at this beach resort. It's a long story but bare with me. Everything started on the 14th of May. My family and I had 4 beautiful days at Chesapeake Beach Resort were we had rented 3 rooms and1 villa. My husband, stepson and I stayed on the Villa. The reason for our family trip was my husband's 60th birthday and Mother day weekend. Like I said, everything was great until the morning we checked out. My husband was in charge of putting all luggage in the car while I was at the front desk checking out. We live in Boca Raton so we are about 2 1/2 hours away from the resort. By the time we get home my son takes the luggage out and he lets me know that the trunk is empty so I don't need to worry about anything. Ok, a couple days go by and on Tuesday night I start to look for my hair dryer and realize the bag I had put my hair dryer, flat iron, my cosmetic bag and jewelry bag is missing. Oh no! I go in panic mode and started looking around the house. Nothing. So I go ahead and call the resort and ask the front desk if any bag it's been reported lost from the cleaning staff. The girl says to me that not to her knowledge and to please call back in the morning which I did. Spoke again to the clerk and she lets me know that the bag is there! Great!!! I think. I explain that I live far away but can make it this past Saturday to pick it up. I explain to the lady that my Cartier watch and other pieces of jewelry are in that bag besides my dryer and toiletries. I said the watch it a 9,000$ watch and other items are 18k gold and hope for them to be there since I put them there my self when packing in the morning of the 14th. So I was relieved to hear the bag was at the office. When I arrived at the lobby the girl goes to the back office and brings my bag inside a plastic clear bag. When I take it out the first thing I noticed is the zipper open to a third of its length, I finish open it and start looking I see everything but my jewelry bag. I noticed my toiletry bag zipper is half way open too... not my style to leave every zipper half way close. So the bad news is all my Jelwery is gone!!!! No watch, no gold hoops no gold ring or chains. ALL GONE!!! Only my dryer, iron and toiletries. Not much empathy from the staff neither. I spoke to the manager who was more worry about me complaining that what was happening to me... very disappointed. Felt so violated and on top not much effort in comforting me. I even doubt my self and offer her to go back home again and check again before going to the police. Finally made it home to double check and this time be 100% sure my jewelry bag was in that bag and somebody took it from me. So today, Sunday 21st finally made the call to the Monroe Sheriff department and made the report for my stolen watch and jewelry for the próx amount of 11,000$. I had to drive down to Isla Morada for the third time in other to file the report and press charges in person so the police can built a case and follow thru with the case. And possibly hope for some kind of closure on this matter and to do the right thing and let people know that no body has the right to violate your personal belongings no matter what. I also told the manager that in the resort staff is somebody who is not honest. So beware of this. My mistake was to forget my bag behind and act a bit late but that is not reason for someone to go into your personal belongings and take what is not theirs. Not cool at all. Hope this message helps prevent another theft. Thank you... and sorry for this sad and long story. Hope the owners choose better next time. PS. I don't hold any personal grouch against the facilities or the good people that work there because is a very nice resort but sadly one bad apple can ruin the entire experience for the rest. Ivette Bless and Julio Aponte. Villa #301 read more

This room had one of the most beautiful views I have ever seen . If you want a nice quiet place to get away with out a crowd this is definitely the place for you . Rooms are renovated and the manager Samantha goes above and beyond her call of duty . Also jazz at the front desk has the best customer service possible ! read more

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Loved our stay. We chose this resort as a convenient more affordable location for day trips to Keywest and access to parks and restaurants in Islamorada and Key Largo. The room was updated, large bathroom and clean. We had 2 queen beds and a living room with couch which worked well for traveling as a family. Having read other reviews it's true there is no bar on site, but you can easily walk to 2 bars, or just get your own beverages and stay put because nothing could be more beautiful than sitting outside on a starry night just watching the sky and listening to the wind rustle the palm trees. Also I was happy with the existing amount of outdoor lighting which includes pathway lights, single solar lights on the tree trunks and strings of lights on the individual cottages. Honestly you can see the stars at night, you feel like you are in nature and I prefer that atmosphere to strings of bright lights. Drug store and grocery store very close by. Staff was friendly and in response to other reviews I never saw any staff consuming champagne. The breakfast was boxed including Jimmy Dean sandwiches you can heat in the room. This worked very well for us traveling with our kids, there was also cereal, granola bars muffins and fruit, so it was healthy enough. I did not mind filling out a daily breakfast form because we don't want waste food and this way you can request exactly what you want to eat. Would be good to be able to submit online in case you arrive back to hotel late. Regarding cleaning it's true they did not clean daily but we don't want a cleaner in the room daily. They were happy to give us clean towels and toilet paper when requested. The staff here are I am guessing mostly local people very down to earth. Some are quiet but I don't equate that with unfriendly. Next time I would stay on top floor because folks above us stepped loudly on floor in the morning. read more

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Generally, it's nice. Good location, clean, rooms were updated, patios are great. Pools, great, beach area, vending machines and ice access, kayaks, fishing poles. It's almost there....no bar is the kicker for me. Not a resort without a bar. I would come back if they had a bar but i prefer Cheeca or Amara Cay - they have it all. There's absolutely nothing to do after dark. Yes, you can go to the liquor store, but sitting at a beach bar is everything. My other negative constructive comment is parking. There are no marked spots and it's just flim flam whatever. Messy! Staff were nice and friendly read more

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. read more

This resort needs to be taken as just a place to lay your head for now. The property is still in very bad shape from the hurricane last year and 80% of the entire property is closed off. Only one building of 20 rooms is being used to house guests and the pool and lobby are accessible. There is no access to the beach whatsoever right now. None of these things bothered me. I go to islamorada often and I typically book whatever accomodations I can find. The prices are high for this resort. I had a voucher from a 3rd party site i use so cost didnt impact my experience. The issue is there are a lot of properties on the island still not opened (postcard inn and islander as example). Therefore boarding in Islamorada is in high demand so while the amenities may not be on site your still paying top dollar due to low supply of overall rooms. This I can see being frustrating to a traveler especially someone dreaming of a keys/beach vacay. My experience was very minimal and good. I only stayed one night and I enjoyed it for what it was. They do offer a voucher to go to Founders Park for free since their beach access is closed off. read more

Even though this place was under construction, it totally exceeded our expectations!! We totally didn't want to leave and wish we had more time to have spent there. Everything new and modern. Super clean and holy moly ROOMY. We had a million dollar view in our King suite. 2 flat screens, one in the living room area and the other in the bedroom. The bathroom is larger than some of the hotels we have stayed in The staff was VERY friendly and accommodating. They extended our checkout due to a late flight. We were able to check in early too. The pool is nice, however we are beach folks so thats where we stayed. Our balcony was huge and we loved sitting there watching the fishermen fish and the iguanas and squirrels climbing the trees, not to mention the obvious coastal scenery. There is not an on-site restaurant however there may as well be bc one parking lot over is an AYCE Seafood buffet and it absolutely did NOT disappoint. (Endless snow crab & beyond). Additionally there is a really cool bar right beside it as well. So glad we found this place. 10/10 recommend read more

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Do not come here thinking it's an actual resort with restaurants in the property and amenities you expect from other REAL resorts in the area. Pay a little more and go stay at others where you can enjoy staying on property without having to leave and go out to grab a bite or even a drink. read more