Montego Bay Villas

Montego Bay Jamaica Villas

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  • Summer Hill Montego Bay 1
  • 9 BR

  • This brightly painted, 3 story villa boasts 10,000 square feet of elegant, yet charming accommodations with a total of 9 bedrooms.

  • $929–$1,643 / night
  • Pool
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  • Silent Waters Montego Bay
  • 8 BR

  • Nestled in the hills of Jamaica, overlooking pristine forests and the spectacular turquoise waters of Montego Bay sits a truly remarkable private Jamaica resort property .... an enchanting heaven.

  • See Rate Sheet
  • Pool
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  • Villas at Half Moon, A RockResort Montego Bay
  • 7 BR

  • For years Half Moon's Royal Villas have played "home away from home" for many discerning clients. These 33 - individual villas with private swimming pools, provide the ultimate Caribbean style escape.

  • $1,175–$3,999 / night 4 Specials
  • Pool
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  • Whispering Waters Discovery Bay
  • 7 BR

  • Whispering Waters, a deluxe 7 bedroom villa overlooks one of Jamaica's loveliest crystal clear bodies of water, Discovery Bay.

  • $2,000–$2,572 / night
  • Waterfront Pool
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  • Amanoka Discovery Bay
  • 7 BR

  • Amanoka - magnificent 7 bedroom villa is the largest and newest villa on beautiful Discovery Bay.

  • Rates by Request
  • Waterfront Pool
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  • Belle Abri Montego Bay
  • 7 BR
    7 BA

  • Completed in 2006, Belle Abri (“beautiful sanctuary”) is a 12,000-square-foot 7-bedroom deluxe staffed villa overlooking the Half Moon golf course, Ritz Carlton, The Palmyra and vast vista of Caribbean Sea. The architecture is dramatic ~ the view is breathtaking.

  • $1,286–$2,286 / night
  • Pool
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  • Fairway Manor Montego Bay
  • 7 BR

  • Fairway Manor is a 6,000-square-foot, 2-story, 7 bedroom private villa overlooking the famous Half Moon 18-hole Robert Trent Jones golf course and the sea.

  • $940–$1,810 / night
  • Pool
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  • Greatview Jamaica Montego Bay
  • 6 BR

  • Greatview is one of the newest and most glamorous private homes overlooking the Half Moon golf course, Ritz Carlton and vast ocean vista.

  • $1,272–$2,200 / night
  • Pool
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  • Summertime Tryall
  • 6 BR
    6 BA

  • Summertime. The setting is breathtaking: five sunny acres of landscaped grounds adorned by an abundance of palm trees, bougainvillea and hibiscus ... large private pool ... vegetable garden ... and wooded grotto with antique stone terrace for sunset cocktails.

  • $786–$1,072 / night 1 Special
  • Pool
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  • Highland House Montego Bay
  • 6 BR

  • Rising from the hills, the seven rooftops of the Highland House cover over 7,000 square feet

  • $929–$1,071 / night
  • Pool
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  • Karma Bay at Tryall Tryall
  • 6 BR
    6 BA

  • A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica.

  • $1,000–$1,715 / night
  • Waterfront Pool
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  • Keela Wee Discovery Bay 1
  • 6 BR

  • Located on a private coral cove, this pretty yellow stone, 6 bedroom villa overlooks one of Jamaica's most peaceful bodies of water ... Discovery Bay.

  • $1,715–$2,143 / night
  • Waterfront Pool
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  • Makana on the Beach Discovery Bay 1
  • 6 BR

  • Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay.

  • $1,858–$2,429 / night
  • beachfront Pool
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  • Malatai on the Beach Montego Bay
  • 6 BR

  • Directly on the turquoise waters of Old Fort Bay in St. Ann‘s Parish, Malatai, is a magnificent new 6 bedroom villa.

  • $1,715–$2,286 / night
  • beachfront Pool
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  • Bambu Montego Bay
  • 6 BR

  • Nine miles west of Montego Bay is a very private hill overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast.

  • $1,179–$1,800 / night
  • Pool
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  • Serendipity Montego Bay
  • 6 BR
    6 BA

  • This villa is newly remodeled with a pleasant balance of elegance, and comfort.

  • $500–$929 / night
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  • Sea Island Montego Bay
  • 6 BR

  • Drive through the impressive entrance gates with their tall stone columns to enter the unique and gorgeous home that is Sea Island.

  • $643–$1,429 / night
  • Pool
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  • Endless Summer Montego Bay
  • 6 BR

  • Endless Summer, a 6 Bedroom turreted mansion with views of the Caribbean Sea.

  • $1,000–$1,429 / night
  • Pool
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  • Wild Orchid Montego Bay
  • 5 BR

  • On 220 private acres of former banana and coconut plantation stretching from mountain to sea, Wild Orchid is a glamorous and luxurious 5 bedroom hideaway in the tropics.

  • $500–$858 / night
  • Waterfront Pool
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  • Windrush at the Tryall Club Montego Bay
  • 5 BR
    5.5 BA

  • Overlooking the manicured Tryall Club golf course and the sea, Windrush is a beautiful 7,000-square-foot private home distinguished by fine antiques, original art and exquisite interior design.

  • $1,429 / night
  • Pool
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  • Cliffside Cottage Montego Bay
  • 5 BR

  • Dramatically perched on a lush green hillside above the sea...

  • $500–$1,000 / night
  • Pool
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  • Pavilion Montego Bay
  • 5 BR

  • Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful.

  • $715–$1,072 / night
  • Pool
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  • Infinity at the Tryall Club Tryall
  • 5 BR

  • Among the newest Premier villas at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea.

  • $1,715 / night 1 Special
  • Pool
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  • Drambuie Estate Montego Bay
  • 5 BR

  • Built in the 1940's by the Duke of Marlborough, Drambuie Estate, a magnificent 5 bedroom villa is a slice of old Jamaica when lively drawing room conversation and gracious service ruled the day in an extraordinary private setting.

  • $643–$1,158 / night
  • Pool
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  • Ian Fleming Villa at Goldeneye Montego Bay
  • 5 BR

  • Fleming's retreat is a boutique resort laced with beaches, tropical forest, caves and secluded nooks. Intimate and informal, this idyll attracts celebrities and other lovers of luxury.

  • $5,500–$6,600 / night 1 Special
  • beachfront Pool
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  • Sugar Bay Discovery Bay 1
  • 5 BR

  • On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay, a 5 bedroom deluxe villa.

  • $1,143–$1,986 / night
  • beachfront Pool
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  • Sunrise Montego Bay
  • 4 BR

  • Right at the water’s edge, Sunrise, a superior, 4 bedroom villa looks out over a private beach and the clear-blue shallows of the Caribbean Sea to a snorkeling reef and the indigo waters beyond.

  • $708–$1,737 / night 1 Special
  • Pool
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  • Hillside Villa at Round HIll Montego Bay
  • 4 BR

  • When Round Hill was only an undeveloped knob of lush green hillside rising over the sea, one man had the good fortune to have his choice of lots, and the wisdom to choose that piece of land most favored by the sun and prevailing trade winds, which also happened to have one of the most spectacular views in all the Caribbean.

  • $600–$1,300 / night
  • Pool
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  • Almond Hill Montego Bay
  • 4 BR

  • Designed by Prince Kasimir Korybut in 1993 and brilliantly renovated in 2012, Almond Hill is a lovely private home located on a former 500-acre coconut plantation just 22 minutes west of Montego Bay and one minute from posh Round Hill where guests enjoy complimentary resort membership.

  • $429–$993 / night
  • Pool
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  • Windsong Montego Bay
  • 4 BR

  • Windsong is an exquisite and very private home four minutes from Round Hill.

  • $500–$1,143 / night
  • Pool
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  • Beach House Montego Bay
  • 4 BR

  • Contemporary 4-bedroom beachfront house on a calm Caribbean bay. Lovers of water sports will revel in this location.

  • $715–$1,272 / night
  • beachfront Pool
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  • Noble House Montego Bay
  • 4 BR

  • Noble House is a unique architectural gem by the sea.

  • $893–$1,108 / night
  • beachfront Pool
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  • Destiny Montego Bay
  • 4 BR

  • Destiny is a dramatic achievement of architecture and design.

  • $1,072–$2,465 / night
  • Pool
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  • Sea Haven Discovery Bay
  • 4 BR

  • Located on a private waterfront acre, Sea Haven is a traditional 4 bedroom West Indian cottage dressed in charming periwinkle blue.

  • $429–$715 / night 1 Special
  • Waterfront Pool
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  • Serenity on the Beach Montego Bay
  • 4 BR

  • Serenity is one of the most beloved and often revisited 4 bedroom villas on Jamaica's beautiful north coast.

  • $536–$1,479 / night
  • beachfront Pool
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  • Tradewinds at the Tryall Club Tryall
  • 4 BR

  • This cozy home sits on two acres at the famous Tryall Club ~ directly on the Caribbean Sea.

  • $708 / night 1 Special
  • Waterfront Pool
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  • Fairwinds Montego Bay
  • 4 BR
    4 BA

  • Fairwinds is a beautiful four-bedroom private home with a magnificent sea view.

  • $565–$1,336 / night
  • Pool
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  • Sunset Montego Bay
  • 3 BR

  • Sunset is a three-bedroom villa with the perfect location for a seaside escape. This beautiful villa sits on the edge of the Caribbean Sea.

  • $786–$2,043 / night 1 Special
  • Pool
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  • Blue Heaven Montego Bay
  • 3 BR

  • A 3 Bedroom deluxe private villa with a sweeping view of the blue Caribbean Sea and Montego Bay.

  • $458–$686 / night
  • Pool
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  • The Cottages at Goldeneye Montego Bay
  • 3 BR

  • GoldenEye overlooks the Caribbean Sea in the quiet village of Oracabessa Bay on Jamaica’s north coast.

  • $560–$1,440 / night 1 Special
  • Pool
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  • Goat Hill Montego Bay
  • 3 BR

  • Goat Hill, a 3 bedroom deluxe private villa, sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea and the most favorable trade winds day and night.

  • $786–$1,072 / night
  • Pool