Top 10 Staffed Jamaica Luxury Villas

With its enticing cultural heritage, beautiful natural surroundings and classic Caribbean lifestyle, Jamaica remains one of the finest choices for a tropical holiday. Given the abundance of joys that it has to offer to the travelers choosing to grace its shores, it’s only natural to want to make the very best of your vacation in Jamaica – and this begins with selecting the accommodation that is likely to provide you with the most authentic and enjoyable experience possible. 

Staying in a luxury home brings privacy, space, and amazing amenities to a vacation, but fully staffed villas really elevate that experience by allowing guests to feel completely spoiled during their stay and there’s no question that Jamaica is the undisputed king of luxury villas that come fully staffed. 

From the moment you check in at any of the homes you will see below, your every need and wish will be personally looked after by a dedicated team of service professionals who are committed to delivering a level of luxury and pampering that you simply won’t find at even the fanciest hotels or resorts. These incredible homes usually include a chef, butler, housekeeper, laundress, gardener, security guard and more.

Private Villas vs. All-Inclusive Resorts

Unlike resorts and hotels that are packed with travelers and tourists, many of our Jamaican villas are nestled in secluded areas and allow for a true sense of luxurious isolation far away from the bustling crowds; and in today’s current travel climate, avoiding crowds is top of mind.

And while hotels often have an atmosphere that is far more contained and enclosed, your own villa rental offers you the opportunity to experience the island from an authentic (yet luxurious) perspective. 

No matter how high the caliber of your chosen hotel, you are always bound to be sharing the space with other guests in some capacity. However, with your very own luxury villa rental, you have the guarantee of complete exclusivity and the promise of being able to escape to your own private haven. No prying eyes. No rowdy neighbors. No sharing of resources with strangers. When you rent a villa, everything is yours for as long as your stay to ensure utter relaxation and privacy for all guests.

Top Staffed Villas in Jamaica

Here is a taste of  some of our gorgeous vacation rentals that offer the exquisite full staff experience you can only receive in Jamaica:

1. Villa Twin Palms

7 Bedrooms • 7 Bathrooms • Sleeps 14 people.

Included Staff: Butler(s), Chef, Gardener, Housekeeper(s), Laundress, Security Guard(s)

Surrounded by ten acres of rolling, manicured lawns and expertly landscaped gardens that contain many specimen trees, Twin Palms commands a strategic position on Barnes Hill with views that take in sixty miles of varying vistas including the ocean. 

This is a house that is designed for entertaining be it on a grand or an intimate scale. The straight lines and elegant enfilade style are naturally conducive to the flow of people and there are many stylish areas where one can retreat to or congregate for private conversation, a game of backgammon or a rubber of bridge. 

The veranda is the center piece to the living space at Twin Palms, offering space to sit, a table at which to dine, a bar to sit at and a pool deck for sunning. The seven multi-tiered pools are centered by a sixty foot infinity-edge lap pool, with a children’s wading pool and whirlpools either side. Close by is the palm court and a secluded fire pit which is strategically placed to capture optimum views of the sunsets for which the parish of Hanover is so renowned.

Book your own stay at Twin Palms.

2. Haystack

10 Bedrooms • 10 Bathrooms • Sleeps 20 people.

Included Staff: Butler(s), Chef, Gardener, House Manager, Housekeeper(s), Laundress, Security Guard(s)

Located on Ocean View Drive, Haystack is surrounded by rolling lawns with lovely sea views to the front and a panorama of the Tryall estate to the rear. Built by a family for families to enjoy, the villa is built on three tiered levels and is notable for its capacious open-plan interiors and free-flowing space.

Formal dining indoors in the striking red dining room affords views of the sea with meals prepared using fresh produce from the villas organic herb and vegetable garden. Outside is a huge veranda, comfortably furnished with an al-fresco dining area and a further lower deck with stylish seating is adjacent to the large heated salt water swimming pool. A fabulous bar with television has recently been installed at one end of the pool.

A spacious entertainment room on the lower pool level is complete with games table, foosball, ping-pong, flat screen TV and bar. Also to be found on the lower level is a comprehensively equipped private gym. 

Book your own stay at Haystack.

3. Promiseas

8 Bedrooms • 8 Bathrooms • Sleeps 18 people.

Included Staff: Butler(s), Chef, Housekeeper(s)

These spectacular side by side villas, each four bedrooms, are beautifully decorated with modern teak, Guango, Spanish Elm, driftwood and stainless steel furniture. The villas also boast a fine collection of contemporary art. In Promiseas 1 there are four master bedrooms all with king-size beds, en-suite bathrooms, Jacuzzi or hot tub and rain showers. Promiseas 2 has three king bedrooms and the fourth bedroom, on the third floor, has four queen beds and is ideal for children or young singles.

Promiseas 1 has a spectacular curved shingle roof, a curved mirrored entrance ceiling with contemporary lighting to highlight all areas and blue mahoe ceilings. The unique design features of Promiseas 2 include a glass atrium in the center of the living room with a beautiful teak tree growing through the open top, third floor Tree House bedroom, living room with spectacular views of the sea, the hot tub in its man-made, underground cave surrounded by bamboo with a bar and massage deck overlooking the sea, and the contemporary lighting. 

Promiseas Villas (1 and 2) can be rented as a five or eight bedroom configuration. These two luxury Premier villas come with two highly trained chefs, three butlers, two housekeepers and an entertainment coordinator/boat tour guide on request. There is a fishing/water sports boat available for rental. The property is equipped with single and double kayaks, life jackets for all ages and fishing equipment.

Book your own stay at Promiseas.

4. Dragonfly

7 Bedrooms • 7 Bathrooms • Sleeps 14 people.

Included Staff: Butler(s), Chef, Gardener, House Manager, Housekeeper(s), Laundress

Occupying a commanding position on Garden Hill, this sensational villa is the perfect space for a luxury getaway. Without a doubt its most outstanding feature is the breathtaking unobstructed view of the ocean that will take your eyes west toward Lucea and east to the twinkling lights of Montego Bay. This most desirable of views can be enjoyed from all bedrooms, living spaces and the magnificent 100 feet swimming pool.

On the upper entrance level are four bedrooms including the master bedroom with an oversized bathroom retreat and private hot tub. The exceptionally capacious free-flowing living spaces comprise a living area, bar, dining and informal sitting veranda and an extra indoor dining room that can double as a board room for executive retreats. 

From the living area you can walk out onto a stunning gazebo which affords full advantage of the surrounding ocean panorama as well as magnificent views of the Tryall Club itself, including the championship golf course. A further three luxury bedrooms are on the lower level off the pool terrace and the enormous heated swimming pool with gazebo which is the largest pool at Tryall. All bedrooms enjoy bathrooms with double showers and their own private exterior seating areas.

As you would expect, there are numerous facilities on hand for guests to enjoy such as a basketball court, home theatre, fully equipped gym as well as a fully stocked games room with x-box and table tennis.

Book your own stay at Dragonfly.

5. Hummingbird House

7 Bedrooms • 7 Bathrooms • Sleeps 14 people.

Included Staff:  Chef, Gardener, Housekeeper(s)

With one of the most panoramic views in all of the Tryall Club and a meticulous attention to detail and design, guests staying at the seven-bedroom Hummingbird House are often so captivated that they book it again before completing their current vacation.

The villa is a sprawling 14,000 square feet residence with a spectacular 50 feet infinity pool, set amidst four acres of beautifully manicured gardens on Barnes Hill. Built in a modern, open, contemporary style, the level of finish and interior design is both striking and exceptional.

There are numerous options for family fun and entertainment including a games area with pool table, a state of the art media centre and an entertainment centre with 70″ HDTV. A recently installed putting green offers guests an opportunity to work on their short game without leaving the comfort of the villa. Up to 14 guests can dine in either the beautiful indoor dining room or outdoors on the breezy terrace. Either way, your meals will be wonderful experiences set against a backdrop of spectacular Caribbean sunsets, and heightened by the culinary talent of your private Chef.

Book your own stay at Hummingbird House.

6. Silent Waters Villa

8 Bedrooms • 6 Bathrooms • Sleeps 20 people.

Included Staff: Butler(s), Chef, Gardener, House Manager, Housekeeper(s), Laundress, Maid

Silent Waters Villa is one of the most glamorous luxury rental villas in Jamaica. This award winning Jamaican holiday home is distinguished by world class architecture, design and decor, breathtaking location, and exquisite accommodations and service. 

Located on one of the highest hilltops overlooking Montego Bay and the Caribbean Sea, the site consists of 16 and a half acres, secured with a sophisticated electronic security and video system, twelve buildings, helicopter pad, private tennis court and two swimming pools occupy five acres. 

Each bedroom suite has its own patio with chaise lounges for sunning and relaxation, all other  sleeping rooms have their own air conditioner and ceiling fans, wet bar, telephone, stereo system, high speed wireless Internet service, LED high definition television with DVD player and iPod docking station. The entire property is rented to only one party of guests at any given time, thereby providing complete seclusion and privacy for the guests.

Silent Waters is a superb property for a family reunion, corporate retreat, destination wedding (seating 54 guests or cocktail party up to 150 guests) or just a small group of friends seeking a most unusual holiday experience. It also includes the gracious staff of 14 who will cater to your every need.

Book your own stay at Silent Waters Villa.

7. Whispering Waters

7 Bedrooms • 7 Bathrooms • Sleeps 14 people.

Included Staff:  Butler(s), Chef, Gardener, Housekeeper(s), Laundress

Located side by side, these neighboring villas combine to offer two swimming pools, two private beaches, two air conditioned gyms and two tennis courts lit for night play. Each villa has its own private coral cove and sandy beach. Both villas overlook one of Jamaica’s loveliest crystal clear bodies of water, Discovery Bay. 

On the main level is the massive Great Room. French doors open wide to a large furnished veranda and bar. Just beyond are the private pool, Jacuzzi, shallow children’s pool, lawn, beach and bay. Upstairs is a second sitting room, entertainment center, internet area and five of the seven bedrooms. Floors throughout are a combination of gleaming wood and imported stone.

Inside and outside dining tables accommodate up to 14 guests. As a special treat, the staff will plan a torchlight beach party, chicken, lobster or fresh-caught fish grilled on the outdoor barbecue. Families renting both villas may have lunches and dinners together on request.

Book your own stay at Whispering Waters.

8. Fairway Manor

7 Bedrooms • 9 Bathrooms • Sleeps 14 people.

Included Staff: Butler(s), Chef, Gardener, Housekeeper(s), Laundress

Fairway Manor is a stylish multi-faceted 10 000 square foot private home. Its rooms feature cool marble floors and overlooks the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea.

Fairway Manor’s well planned rooms open onto terraces and balconies where the sweeping panorama of multi-colored gardens, lush green golf course and deep blue Caribbean Sea is truly breathtaking. Each level features a central large living room and spacious open-air areas for drinking and dining, playing pool or watching sports, movies, etc. on either of two 52″ televisions. 

Special guest membership in Half Moon provides a remarkable golf, beach and tennis package for Fairway Manor guests. In addition to the Half Moon golf package, available literally in your front yard with pro shop walking distance from Fairway Manor, more world class golf is five minutes away at Cinnamon Hill and challenging White Witch.

No description of Fairway Manor is complete without mention of its delightful staff. Apart from routine duties, Butler Roy Tomlinson actually designed and laid out all the gardens on the property, and planted them with help from staff members Richard, Olive, Veronica and Janet! 

Book your own stay at Fairway Manor.

9. Jubilation

6 Bedrooms • 6 Bathrooms • Sleeps 12 people.

Included Staff: Butler(s), Chef, Gardener, Housekeeper(s), Laundress

This magnificent villa is located on Mahogany Drive with the entrance driveway on Ocean View Drive. Constructed to the highest of standards and quality and with lovely sea views, Jubilation sits surrounded by a mature, beautifully landscaped garden that has become the favourite habitat of birds. The villa kitchen is regarded as being one of the best-equipped at Tryall, the swimming pool is huge and the sheer amount of veranda and patio space make it a perfect home for entertaining in.

The large master bedrooms feature king size four poster beds with lavish en suites complete with Travertine tiles, marble vanities, copper sinks and exotic clawfoot tubs. Both bedrooms open onto the full length terrace which overlooks the pool and with ocean and garden views.

The spacious living and dining areas are furnished with interesting works of art with doors that fold back allowing the breezes to come in. A separate entertainment room on the lower level comes with a 60″ television, games, music system, books as well as an adjoining bathroom and door that open to the lower veranda, bar and pool area. 

A skilled and charming staff of five are on hand to provide the legendary hospitality that Jamaica is renowned for.

Book your own stay at Jubilation.

10. Following Seas

6 Bedrooms • 6 Bathrooms • Sleeps 12 people.

Included Staff: Butler(s), Chef, Gardener, House Manager, Housekeeper(s), Laundress

Commanding a strategic position atop one of the highest points of Tryall, Following Seas is a gracious, visually arresting house that combines the attributes of a much-cherished family home with the world-class facilities of a boutique hotel and the aura of old Hollywood glamour.

Space is a keyword where everyone can come together or retreat to their own favourite newly-discovered corner. An expansive covered terrace with a dining area overlooks the sparkling infinity pool as well as the ocean with a separate private Jacuzzi spa and terrace further along. 

With a deck that overlooks the magnificent bay and perfectly placed to observe the setting sun is a large media cottage complete with an 80 inch flat-screen television and bar area. A perfect square with the original fretwork tray ceiling, the drawing room is one of the loveliest at Tryall and a perfect place to escape with a book.

Each bedroom has a private double bathroom expertly fitted with marble and granite custom-built cabinetry and crystal cupboard and draw handles that mirror the colour of the bedroom walls.

Book your own stay at Following Seas.