3,902 private villas and vacation homes worldwide, arranged by your Aspen Travel Advisor. VIP travel benefits, zero membership fees.
Caribbean · Jamaica · Ocho Rios
Magnificent 14-acre oceanfront estate. Here is the rich character of The Riviera married to the superb service of Colonial Jamaica ... on a magnificent seascape just west of Ocho Rios on Jamaica's renowned north coast. Rio Chico's guest list includes diplomats, industrialists and celebrities from around the world.
Caribbean · Jamaica · Montego Bay
Its remarkable architecture defines spacious bedroom suites, a long furnished verandah, a striking inside dining room and large family play room ~ all enhanced by overviews of the long private pool and acres of landscaped lawns and breathtaking views of the deep blue Caribbean Sea.
Caribbean · Jamaica · Ocho Rios
17th Century fortress restored as a remarkable private home on a perfect private Caribbean beach.
Caribbean · Jamaica · Discovery Bay
This 13,000 sq ft villa is complemented with luxurious and beautiful finishes. Happy Hour villa is a resort in itself, with a calm sandy beachfront, tennis/pickle court, gym, spa, sauna, games room, media room, infinity pool, Baja ledge/kiddies pool, hot tub, indoor/outdoor living & so much more.
FeaturedFree Night(s)Caribbean · Jamaica · Ocho Rios
Malatai on the Beach | Stay a Little Longer
MALATAI is a fabulous contemporary home with modern updated bedrooms and noteworthy bathrooms nestled on a wide beachfront on the beautiful Old Fort Bay Beach. While privately located, Malatai is only minutes from Dolphin Cove, famous Dunn‘s River Falls, and lively Ocho Rios with its wide selection of duty-free shopping, excursions, and music.
Caribbean · Jamaica · Ocho Rios
Sea Salt is a fabulous new property to our portfolio, located on Old Fort Bay, making this lovely half-moon beach one of our premier locations. Sea Salt is made up of a 5-bedroom main house on the beachfront with two 2-bedroom cottages set back from the beach with an expanse of tended grass lawns reaching down to the sea. Offering 9 bedrooms, beachfront, and a top-rated staff, near Ocho Rios.
Free Night(s)Caribbean · Jamaica · Ocho Rios
Jamaica | More Nights, More Luxury!
In the 1950s, Kingston attorney Clinton Hart happened onto this remarkable 3-acre waterfront location, bought it, and built a simple beach cottage for his family. Through four generations, Canoe Cove has been a beloved family home, virtually unembellished. In 2015, Hart’s grandson replaced the worn cottage with a new sort of architecture, straightforward, uncomplicated, and loaded with thoughtful comforts and essentials to redefine luxury in a beachy, barefoot lifestyle.
Caribbean · Jamaica · Ocho Rios
Aquamarina boasts updated, contemporary interiors, with every room offering breathtaking views of the Caribbean. This stunning 6,000 sq. ft. villa overlooks crystal-clear waters and features a private sandy cove and one of the island’s finest beaches.
Free Night(s)Caribbean · Jamaica · Ocho Rios
Jamaica | More Nights, More Luxury!
This stunning 8-bedroom villa is located right on the water’s edge, overlooking the crystal clear blue waters that Ocho Rios is well-known for. Entry to the villa is through the private compound of Hermosa Cove Boutique Resort.
Caribbean · Jamaica · Ocho Rios
Promiseas Villas are located on a fabulous private sandy cove which are newly completed and exceptional in every way imaginable.
Caribbean · Jamaica · Montego Bay
Occupying a commanding position on Garden Hill, this sensational new villa is a dramatic new addition to the Tryall Club.
Free Night(s)Caribbean · Jamaica · Montego Bay
Tryall Club | 2026 Caribbean Nights
Discover the epitome of Caribbean sophistication, opulence, and breathtaking vistas of Oceana, a true masterpiece located amidst nature’s grandeur atop Garden Hill at The Tryall Club. Oceana, built from the ground up, is simply awe-inspiring. With wide-angled views of the Caribbean Sea, the city lights of Montego Bay to the east, and the island’s westerly views, the scenic offering from this private villa will exceed expectations.
Caribbean · Jamaica · Montego Bay
This amazing seafront property is one of the newest premier villas at Round Hill.
Caribbean · Jamaica · Montego Bay
Harmony Hill is a private oasis offering the finest in Caribbean living, combining Jamaica’s rich architectural tradition with today’s modern amenities and service.
Caribbean · Jamaica · Montego Bay
Perched atop the legendary Round Hill Estate, Hillside House embodies the timeless charm of Old Jamaica paired seamlessly with modern luxury. This crowning jewel has long been a show-stopper, celebrated for its breathtaking panoramic views and cooling trade winds that sweep effortlessly through the property. Thoughtfully designed with families in mind, Hillside House offers inviting, unpretentious elegance — a relaxed yet refined retreat created for savoring the very best of island living.
Free Night(s)Caribbean · Jamaica · Montego Bay
Tryall Club | 2026 Caribbean Nights
Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish bathrooms throughout.
Caribbean · Jamaica · Discovery Bay
On a stunning promontory, once the site of an old stone fort, sits a remarkable home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue Caribbean Sea on the other.
Caribbean · Jamaica · Discovery Bay
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with a private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayaking water.
Caribbean · Jamaica · Montego Bay
Hummingbird House is one of the finest properties within the Tryall Club!
Caribbean · Jamaica · Montego Bay
Pineapple House is a spacious villa located on Copper Ridge with a magnificent 180 degree view of the Caribbean Sea located on Jamaica’s exclusive North Shore
Caribbean · Jamaica · Discovery Bay
Located on beautiful Discovery Bay, Amanoka is one of the most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water, and waterfront gazebo with suspended canvas swings.
Free Night(s)Caribbean · Jamaica · Montego Bay
Tryall Club | 2026 Caribbean Nights
A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay.
Free Night(s)Caribbean · Jamaica · Montego Bay
Tryall Club | 2026 Caribbean Nights
Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee and driving range are within walking distance of the Phoenix front door. Nine laykold tennis courts are just a golf cart ride up the hill.
Caribbean · Jamaica · Ocho Rios
Villa Lido is a fabulous brand-new contemporary beach house, constructed in 2021. Situated right on the white sand, the half-moon beach at Old Fort Bay. Beautifully designed and finished, incorporating family heirlooms and a chic modern vibe. Music, its history & its relevance today are foremost in its concept.
