For the third straight year, we chose Round Hill Resort, in Jamaica, for our February week away with our 3 young adult children. Jamaica is good for us because we have a non-stop flight from Baltimore to Montego Bay. Other islands we like (e.g. BVI) involve an all-day struggle to get there.
What we like about Round Hill: It is a small to moderate size resort with all amenities well scaled for resort size (in other words, you don't have to get up early to claim beach lounge chairs or worry that you won't get a spa appointment. There are plenty to go around.). The resort is casual elegant (maybe the term is understated elegance), by which I mean very classy (good service, very lovely landscaping, lovely rooms overlooking the ocean.) Management is very helpful and accommodating about special needs.
But here's what really keeps us going back to Round Hill: really good food (best we have had in the Caribbean); really great and convenient water sports program staffed by very helpful and competent staff (I did my fist Scuba dive with them a year ago and repeated it this Feb.). And lots of water sports activities are free -- Hobie Cat sailboat, kayaks, snorkeling at reef right off the beach (this is the best!). And there is plenty of shade on the beach so that our 2 non-water sports family members can sit in the shade and read all day, without being cut off from those of us doing water sports. Also, we always get massages at the spa, which we like a lot. And the fitness-center staff is helpful, too. Really, all I can say about writing this review is that I feel like I'm giving the world my precious secret. But since I can only be there one week a year, I guess I should share.

Generally, this is a nice place, not so much a resort along the lines of Half Moon Bay as a club consisting of villas that dot a hillside above an old school beach club. The villas are the reason to come here. They are historic and, if you book a whole one, private. (If you book only a villa suite, the way they are designed with common space, your enjoyment may vary with whom you get as fellow villa occupants.)

This is not the place to go if you are seeking open, tropical beaches with turquoise water. The beach is a cove with every chair occupied (at least in January) and partially paved. Beachside rooms, while nicely appointed, are close together. The beach is a nice place to read a book but there is no space for a beach walk. Swimming and water sports are limited by a reef about 50 feet out that is off limits due to sea urchins. (The beach is good for toddlers as the water is calm and shallow.)

The one issue we had is that the resort is not entirely forthcoming about the cost of meal plans. At the the advice of others on Tripadvisor, we booked the platinum plan, advertised at $180/person/night as all inclusive. It turns out the full price is $225 or $450/couple/night or $3150/week, enough for a room at some resorts. The flyer they give you describing the plan says service and taxes are included but they aren't. The extra 25% is mentioned elsewhere but only in the fine print. All in all, a nice spot. When comparing with other resorts, just be sure to budget for the extra 25% you will be charged at checkout..

I just had the most wonderful and relaxing time at the Round Hill Hotel & villas. I stayed in cottage #2. The cottage itself, while well apportioned in space and accommodation, some of the furniture could be updated. That being said, the staff was wonderful and took care of us in an attentive and caring way. The Round Hill property as a whole was a dream. It was relaxing and offered the amenities that a high end resort is expected to provide in great style. My greatest compliment is reserved for the absolute feeling of safety I felt. The doors need not be locked and your belongings were secure even without you being there. I highly recommend it even though for many it seems a little pricy, it was well worth the splurge.

One of the most relaxing, enjoyable experiences of my life. We stayed at the hotel on the beach for 7 nights, and everything was just marvelous. The food was excellent, the staff extremely accommodating, and the landscaping and architecture were exquisite. I went with my family, along with my 2 and half year old son who had a blast. I have never written a review on trip advisor, but need to spread to good word about Round Hill.