Round Hill Hotel and Villas

Opened in 1953, the property was conceived as a place for well-heeled artists and socialites to build private cottages, which would then be run by a hotel. It attracted well-known names such as Adele Astaire, Oscar Hammerstein, and John F. Kennedy, and has since become one of the most impressive properties in Jamaica. Immersed in carefully crafted flora, Round Hill is one of the few Jamaican resorts that actually feels like it's in an exotic, far-away land. It's secluded, lush setting spans 110 acres, and is filled with hanging vines, seashell-filled sand, fruit trees, and lawns with hammocks. It retains a classic, plantation-style design, with original checkered floors at the lobby, an 18th-century chandelier with candles that are lit nightly, and lots of colonial-inspired furnishings. 

It's previous life as a pineapple plantation can be felt in the hotel's pineapple logo, which decorates signage and a piece of artwork made by a local artist in the TV room. A large garden is at the top of the hill, and produce such as peppers, mint, and mangos are used at the restaurants. Guests can take a weekly tour of the garden, though most tend to spend their time by the pool and beach, often reading or chatting with the well-regarded staff. The crowd is a mix of quiet couples and young families, who seem to coexist peacefully -- a kids' club and private nannies help with this. Plus, couples can head to the spa side, which has a verdant lawn with sunbeds and hammocks, and is adult-only.

Outside Montego Bay, Round Hill is located in Hanover Parish, set a 35-minute drive from Sangster International Airport. It has a secluded, quiet location that's about a five- to 10-minute drive from the small town of Hopewell, where there are some restaurants, churches, and banks. Guests rarely leave the grounds, unless to find cheaper dining options or visit the famous Tryall Golf Course, a 10-minute drive away. Parking is free on-site.

The resort consists of 27 hillside villas (divided into 74 suites) and 36 rooms that were designed by Ralph Lauren (a member of Round Hill's board of directors and the owner of two homes on-site). The hotel-style units are split across two sea-facing floors, but only the lower level rooms have furnished outdoor spaces. Immaculate rooms have bamboo four-poster beds, beige tiling, white walls and linens, and pops of blue and pink in throw pillows and blankets. Ceramic pottery, pineapple-shaped lampshades, and silver kettles add upscale touches. Second-floor rooms have white shutters that open to pretty vistas, while all have comfy armchairs, air-conditioning, iPod docks, desks, coffeemakers, closets with safes and mini-fridges, and free Wi-Fi. No TVs are provided. Bathrooms come with deep tubs and separate rainfall showers, dual sinks, Elemis bath products, and hairdryers. 

Villas are farther from the beach and amenities, but dotting the hillside, they offer lovely ocean vistas. All are individually owned and decorated, though expect a similar plantation-style design across the board, with rich wood furniture, chic linens and decor, and classic touches such as four-poster beds. Units come with living spaces, furnished outdoor spaces, and kitchens -- where breakfasts are prepared each morning for guests. Most of the villas have private pools, and they have up to six bedrooms. Swish bathrooms have tubs and separate showers, some of which are located outdoors.

A small but lovely beach area has calm water, loungers, and umbrellas, plus an adjacent bar. Also in this area is a good-sized infinity pool with gorgeous ocean vistas and a shallow section for kids. Adults looking to escape kids can head to the spa side of the hotel, which is adult-only and has ample space for guests to lounge on chairs or hammocks. The spa has a small circular pool of its own, as well as a full salon, indoor treatment rooms, and garden set massage area with chakra showers. Also in this area is a windowed, well-equipped fitness center and a pavilion where yoga and fitness classes take place (for a fee).

For more activity, non-motorized water sports and tennis courts are included. Kids can keep busy at the Pineapple Kids' Club, which is free and has activities for children of all ages. Nanny service is also available for a fee. Next to the kids' club is an area where local merchants sell goods such as handbags and wood carvings. For those missing their TV or wanting to watch a sporting event, the Pineapple Room has a large TV and comfy couches. A library offers a collection of books and additional seating.

Round Hill is a popular spot for weddings thanks to its beautiful grounds. The property can host up to 150 people in various spots -- yoga pavilion, beach, and private villas, for example -- and they have a limit of one wedding per weekend. 

The Round Hill has a few modern, Caribbean-inspired dining and drinking options, all of which are well-reviewed. The upscale Restaurant at Round Hill is a seasonal eatery open from mid-December to March. Reservations are required The Grill is an upper-level eatery with fantastic ocean views and tasty food all day. The Seaside Terrace restaurant is casual and has themed evenings that include farm-to-table, beach barbecue, and Jamaica nights. Between the beach and pool is a hut-style bar. Afternoon teas are free, as are weekly manager receptions with free cocktails. 

Food is a bit pricey across the board, which is why some guests opt for the all-inclusive package that covers meals and alcoholic and non-alcoholic beverages.