At one time or another, I have been a guest at some of the finest hotels in the world: The Peninsula (Hong Kong); The Connaught (London) ; Le Richemond (Geneva); Splendido (Portofino), The Carlyle (New York), The Meurice (Paris), just to name a few. I will just say this: my recent five day stay at Round Hill tops them all. From the moment I entered the registration area, the experience was simply sublime. The location, the friendliness of the entire staff, the cleanliness, the entertainment, and the food were superb. How on earth can each member of the staff, up and down the line, learn, and remember, your name in such a short period of time? And every greeting is with a warm and genuine smile. The accommodations at The Pineapple House overlook a crystal clear bay and a stunning nightly sunset. As well as being beautifully decorated in the vintage Ralph Lauren (his "Cottage 26" is right next door) style, they are spotlessly clean. It is no wonder that JFK and Jackie spent part of their honeymoon in one of the Villas! If you are partial to understated, low key, and effortless style, this is the place! Round Hill does not bluster with glitz, it whispers to you with elegance! Sitting in the open air bar, before dinner, sipping a dry martini, and listening to a great pianist play Gershwin and Porter songs is my idea of Heaven. I intend to spend a week at Round Hill every year for the rest of my life. A food tip: the simply grilled Grouper will take your breath away! It was swimming a few hours earlier! For me, Round Hill is a treasure that I finally found!

Round Hill is a nice place to stay, esp. for families & if you have a villa. They have an illustrious history & they can clearly still trade off of that (Hence the caliber of celebrity that stay there). Ralph Lauren has his own Villa (which is gorgeous of course) & another famous person stayed when we were there. However, we felt the place was a bit of a fading glory. It still has Charm to spare but the main parts were definitely run down. The Library, TV room & upper tier of restaurant were a bit sad & smelled musty. The whole thing had this Mrs.Haversham kind of feel to it. You know in it’s Hey day it was absolutely stunning & you can see the remnants of that.

MAJOR TIP for Couples: MAKE SURE, you do not book during a school break. THE REASON: ALL of the Rooms overlook the 1 pool & there are NO actual windows (just shutters). That means from as early as 7:30am you start hearing the squealing excitement of children. ALSO, BE SURE, to ask for a room W/OUT an interconnecting door. You can hear EVERYTHING your neighbor says anyway.. but it becomes worse with the door. The neighbors kid kept opening the it & coming into our room! We had to be moved. Concierge tried to act surprised & say no one has ever asked for that before but we insisted. It was much better. Yet, every morning & evening we still heard ABSOLUTELY EVERYTHING our neighbors below us were talking about & they were not being loud.

So a few Con’s before we get to the Pro’s:
No in room amenities: Management’s policy ...”we want people to relax so no TV’s in rooms”. Well.....we are all adult’s & on holiday we should be able to relax as we choose. We thought it was a bit of a con that they don’t provide rooms w/TV’s/DVD’s. Only upon rental ($30 per day) & it’s an Old TV from the 90’s! However – b’c of the lack of privacy (proper windows) we can understand why they had to implement no TV’s. We just don’t like the BS excuse they give. Also – absolutely no in room bar. Again – if you want a refrigerator you have to pay a daily rental fee & for it alone. They also don’t stock it. You have to tell them what to put in.

Housekeeping: Was a little lackluster. Mold on our lampshades & the grout in our bathroom. We killed a large roach under our chaise (which was raised off the floor by 2 Ft.) & the remanants of the stain were there our entire stay (meaning HK didn’t mop the full floor even w/easy access). The room books were never wiped down, they had a dusty/greasy film....stuff like that.

Spa: Weird Set-up. No Chill out room before hand & the massage room was shared! There was only a partial partition wall, so again heard the next door massage begin/end & the use of the bathroom (which is also in that room) & it’s Utility closet being used. Distracting.

Grounds: A Tire washed up on shore from the path to & from the spa. It was never removed & it could have been. No separate quiet Adult pool. Needs major freshening.

Villas: We felt that it did cater to their regulars. So much so, a woman felt comfortable enough to breastfeed (w/out covering up) in the middle of dinner. The sat very central & were very obvious b’c they hung in a large clique.

We also had roaches in our bathroom every night. We did call front desk to ask if this is normal & they said Yes, esp. after the rain. So we VERY much appreciated their honesty. It’s just a little nerve-wracking to be brushing your teeth & have a roach crawl over your foot when on vacation. They were only in our bathroom (except once). Mainly under the sink. So there was probably something to that.

PROS: The pool is beautiful. The View from the upper floor rooms are exactly as the website shows. The staff were mostly very curteous & friendly. It is definitely a fantastic set-up for children. My massage (w/Cassandra) was excellent. Food was pretty solid. Super easy to get to especially if you want a last minute-quick break from Tri-State area. The shop was great! Well priced items, not too crazy. Beach Buffet & Jamaica Night is fun! Esp. for kids.

All in all, Round Hill is good. I think Families would & do love it! It is really set up for that. The have much to offer. As far as luxurious, it’s a bit overrated yet it is very sweet. It charges the prices but isn’t choice, little details, total privacy & quiet... a luxury most people pay for? I say it’s great as a quick last minute escape for a few days! But for a really long holiday as a couple & for $125 more a night, try Las Ventanas.

Round Hill is a truly special place. It says in the brochure that it is like putting on a cashmere sweater, which is a wonderful description and so apt.. You instantly feel comfortable and looked after the minute you step through the beautiful reception area, instantly staring out at the views of the bay.
We went with children aged 6 and 9 - on our third visit. It's wonderful to realise the children can experience freedom in an incredibly safe environment. The beach and pool staff are always keeping an eye on their safety and well being.
The staff, most of whom have been there for many years, find nothing too much trouble - from trekking across the beach in 80degree heat with a tray of food for the children, to serving you an ice cold pina colada by the pool.
We cannot fault the cleanliness of the rooms, the restaurant or any of the facilities. All make the most of the views and provide a very relaxing environment to be in.
If you are looking for a luxurious holiday in peaceful surroundings, then this is the perfect place - a testament to the fact we have been back three years running. There is also, however, plenty for the children to experience as well. It's up to you what you wish to do with your time, and any requests are granted without question.
Another lovely point about Round Hill is that, because it is relatively small, you are able to meet and chat with like-minded people, if you so wish.
The food is varied and delicious, although there is only one restaurant, they take care to provide a wide selection of many different tastes.
This is a truly stylish place, steeped in history ... as you will note when you see the pictures of all the stars who have visited over the past years.
But it's just as good for families!

This is a long overdue review. I've been browsing this site, looking for another all-inclusive place to go next year on family vacation, and what I'm discovering is that NOTHING seems to compare to Round Hill. We were there in December with our 3- and 5-year-olds. I have traveled pretty extensively in my lifetime, so I have a good sense of what constitutes a quality resort.

ACCOMODATIONS: Just beautiful, elegant Caribbean (dark wood and white). We stayed in a one-room in The Pineapple House. They told us to book one room and an adjoining one for the kids, but they wouldn't sleep alone so they allowed us to cancel the other room.

KIDS ACTIVITIES: We left our kids at the Pineapple Club for parts of the day. The nannies there were incredibly sweet and caring. The club is small--really, just two rooms--and the toys are old-ish and worn. But, that's me seeing it through my adult eyes. The kids didn't care, they had a lot of fun! And they did activities with them, drawing pictures, making pictures, etc. We had a dedicated nanny, Francine, because my son has some disabilities, and she was just so wonderful. One day, she paddled my son around on a paddleboat for a half hour because he didn't want to get off! Speaking of staff...

THE STAFF: Unparalleled; we have never had such courteous, genuinely nice, NO attitude service. Everyone was cheerful and incredibly accomodating at all times.

THE FOOD: Like a reviewer below, we probably gained 5 pounds on this vacation! We've never before experienced this level of quality in resort food. We got the all-inclusive plan, and wow, did we eat. My husband basically ordered a crab leg with every meal! I loved the salmon, the steak, the salads. Everything.

In sum, Round Hill is an outstanding resort. We like to see new places every year so we're not going back but I may regret that decision because after Round Hill, everything else will pale slightly in comparison.