Name Highlight Activity Duration Price Season Destination Sunrise at Tryall - Montego Bay, Jamaica, W.I. - View Details Sunrise looks out over a private beach and the clear-blue shallows of the Caribbean Sea to a snorkeling reef and the indigo waters beyond. The villa is supplied with full household staff. Villa Rentals USD 630 - 1535 Per day St. James Sunset at Tryall - Montego Bay, Jamaica, W.I. - View Details 3 Bedroom Villa on Country Club Drive - Rating: DeLuxe. Sunset is a three-bedroom villa with the perfect location for a seaside escape. The villa is supplied with full household staff. Villa Rentals USD 785 - 2045 Per day St. James The Wharf House - Montego Bay, Jamaica, W.I. - View Details Imagine a 300-year-old cluster of hand-hewn stone buildings next to the sea. The villa is supplied with full household staff. Villa Rentals USD 429 - 1358 Per day St. James Thomas House - Montego Bay, Jamaica, W.I. - View Details In the Walt Disney film "Cool Runnings," Thomas House is a spacious ocean-view villa overlooking the first fairway of the Half Moon golf course. The villa is supplied with full household sta Villa Rentals USD 550 - 1300 Per day St. James Tradewinds at Tryall - Montego Bay, Jamaica, W.I. - View Details Tradewinds sits in an exclusive location right on the shore of the Caribbean Sea. The villa is supplied with full household staff. Villa Rentals USD 710 - 1740 Per day St. James Tranquility on the Beach - Montego Bay, Jamaica, W.I. - View Details True to its name, Tranquillity is a place for relaxing into the calm ambiance of an exquisite home on a beautiful waterfront site ... The villa is supplied with full household staff. Villa Rentals USD 715 - 2072 Per day St. James Villa Mawr - Montego Bay, Jamaica, W.I. - View Details Villa Mawr is a comfortable four bedroom ocean view villa on an acre and a half of lush tropical gardens. The villa is supplied with full household staff. Villa Rentals USD 472 - 929 Per day St. James Villa Olga - Montego Bay, Jamaica, W.I. - View Details The beautiful and fully staffed, Villa Olga is located on the north coast of Jamaica six miles east of magical Montego Bay. The villa is supplied with full household staff. Villa Rentals USD 172 - 515 Per day St. James Villa Rococo - Montego Bay, Jamaica, W.I. - View Details Villa Rococo captures the allures of western Jamaica hillside sharing an ideal spanning of hundreds of acres of lush mountains and embracing valleys. The villa is supplied with full household staff. Villa Rentals USD 429 - 1429 Per day St. James Villa Viviana at Tryall - Montego Bay, Jamaica, W.I. - View Details A most serene and enchanting location, Viviana is the ideal place to re-discover the secret to falling in love with nature and with life. The villa is supplied with full household staff. Villa Rentals USD 2143 - 4286 Per day St. James Vista Del Mar at Tryall - Montego Bay, Jamaica, W.I. - View Details Tradewinds sits in an exclusive location right on the shore of the Caribbean Sea. The villa is supplied with full household staff. Villa Rentals USD 630 - 1535 Per day St. James Wheel House at Tryall - Montego Bay, Jamaica, W.I. - View Details 6 Bedroom Villa on Copperwood Ridge - Rating: Superior. Welcome to the Wheel House Villa! The villa is supplied with full household staff. Villa Rentals USD 945 - 2250 Per day St. James Wild Orchid - Montego Bay, Jamaica, W.I. - View Details Wild Orchid is a glamorous and luxurious hideaway in the tropics. The villa is supplied with full household staff. Villa Rentals USD 500 - 1821 Per day St. James Windrush at Tryall - Montego Bay, Jamaica, W.I. - View Details Windrush is a most captivating villa with its polished, luxe Caribbean style and elegant verandah setting embracing the outdoors. The villa is supplied with full household staff. Villa Rentals USD 1100 - 2750 Per day St. James Windsong - Montego Bay, Jamaica, W.I. - View Details Windsong is an exquisite and very private home just minutes from Round Hill. The villa is supplied with full household staff. Villa Rentals USD 500 - 1429 Per day St. James Xanadu at Tryall - Montego Bay, Jamaica, W.I. - View Details Xanadu offers spectacular views of the rolling green fairways of Tryall Club’s championship golf course. The villa is supplied with full household staff. Villa Rentals USD 1100 - 2750 Per day St. James Yellowbird at Tryall - Montego Bay, Jamaica, W.I. - View Details This beautifully appointed four-bedroom villa completed in 1991 offers spectacular views of Tryall Club’s golf course and the Caribbean Sea. The villa is supplied with full household staff. Villa Rentals USD 865 - 2280 Per day St. James Azure Sky - Negril, Jamaica, W.I. - View Details Azure has the finest “play room” in Negril. Perfect for family relaxing, large parties, or wedding receptions. The villa is supplied with full household staff. Villa Rentals USD 1700 - 2500 Per day Westmoreland Bay Whisper - Negril, Jamaica, W.I. - View Details This villa sits directly beachfront, being all that separate you from a private, pristine beach and the blue green waters of the Caribbean. The villa is supplied with full household staff. Villa Rentals USD 1700 - 2500 Per day Westmoreland Dream Walk - Negril, Jamaica, W.I. - View Details Located on the beach, Dream Walk is 3500 sq ft of luxury. The villa is supplied with full household staff. Villa Rentals USD 1200 - 1700 Per day Westmoreland Ginger Breeze - Negril, Jamaica, W.I. - View Details The elegant living room with wet bar, PC, and stereo boasts breathtaking views of the Bay and the famous Negril sunsets. The villa is supplied with full household staff. Villa Rentals USD 1700 - 2500 Per day Westmoreland Lilac Mist - Negril, Jamaica, W.I. - View Details The Honeymoon Villa! We invite you to experience the finest rental accommodations in all of Negril, Jamaica. The villa is supplied with full household staff. Villa Rentals USD 600 - 800 Per day Westmoreland Avalon - Ocho Rios, Jamaica, W.I. - View Details Avalon Villa is a beautiful one story villa nestled in a lush tropical garden overlooking the sea. The villa is supplied with full household staff. Villa Rentals USD 429 - 529 Per day Saint Ann Carey Island - Ocho Rios, Jamaica, W.I. - View Details If living like royalty is your vacation fantasy, then Carey Island will make your dreams come true! The villa is supplied with full household staff. Villa Rentals USD 643 - 1786 Per day Saint Ann Carib Apartment - Ocho Rios, Jamaica, W.I. - View Details Beautiful and private One bedroom duplex apartment overlooking the Caribbean Sea. The villa is supplied with full household staff. Villa Rentals USD 250 Per day Saint Ann previous 25 vacations  -  1  -  2  -  3  -  4  -  [ 5 ]  -  6  -  7  -  8  -  9  -  next 25 vacations