Jamaica Villas

Jamaica is one of the most popular villa rental destinations in the Caribbean. Known for its friendliness, beauty, and laid-back lifestyle, Jamaica is the perfect island getaway. From its fabulous beaches and villas, to its world-class golf courses, Jamaica has something for everyone. Many visitors to Jamaica prefer to rent a villa for the luxury, convenience, and value it offers. With so many different types of residences in our extensive collection of Jamaica villa rentals, you’ll be sure to find something that suits your style.  Read More

About Jamaica

The Jamaicans say "Out of Many, One People", and it is true. Jamaica's diversity offers something for every vacationer! more

6+ Bedroom Jamaica Villas

    • Hanover Grange at Tryall Photo
    • Hanover Grange at Tryall Tryall
    • 9 BR
      9.5 BA
    • Hanover Grange is one of the latest additions to the Tryall family of Estate Villas. The homeowner is Jamaican-Born Theresa Roberts who has lived for many years in the United Kingdom but now divides her time between Knightsbridge in central London and Hanover Grange.

    • $2,013$6,494 / night
    • Pool
    • L’Dor V’Dor at Tryall Photo
    • L’Dor V’Dor at Tryall Tryall
    • 9 BR
      12 BA
    • Tucked away on a hill overlooking the majestic Tryall Club and providing 360 degree panoramic views of Montego Bay and Hanover, L’Dor V’Dor is a haven waiting to be discovered. The largest villa on the property, it is perfect for large families or family groups.

    • $1,948$6,494 / night
    • Pool
    • Sundown Photo
    • Sundown Discovery Bay
    • 9 BR
      9 BA
    • Nestled in the secluded Discovery Bay, on Jamaica's North Coast, Sundown Villa epitomizes what an exquisite, vacation villa should be.

    • $1,500$4,571 / night
    • Pool
    • Haystack at Tryall Photo
    • Haystack at Tryall Tryall 1
    • 8 BR
      8.5 BA
    • 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.

    • $1,558$5,195 / night
    • Pool
    • Rio Chico Estate Photo
    • Rio Chico Estate Ocho Rios
    • 8 BR
      8.5 BA
    • Rio Chico sits on what some have called the most beautiful site in all the Caribbean. Built in 1898, the villa recently underwent a lavish renovation by one of the world's most brilliant hoteliers.

    • $7,857$10,821 / night
    • Pool
    • Silent Waters Photo
    • Silent Waters Montego Bay
    • 8 BR
      6.5 BA
    • Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-class architecture and design, breathtaking location, and exquisite accommodations and service.

    • See Rate Sheet
    • Pool
    • A Summer Place on the Beach Photo
    • A Summer Place on the Beach Discovery Bay
    • 7 BR
      9 BA
    • Nestled on its own sandy beach by the blue waters of Discovery Bay, A Summer Place is a spacious and playful family home.

    • $1,571$3,500 / night
    • beachfront Pool
    • Amanoka Photo
    • Amanoka Discovery Bay
    • 7 BR
      7.5 BA
    • A favorite of celebrities and discerning vacationers, Amanoka promises a luxurious and truly enjoyable vacation.

    • $2,000$4,286 / night 1 Special
    • Waterfront Pool
    • Fairway Manor Photo
    • Fairway Manor Montego Bay
    • 7 BR
      9 BA
    • Stunning for its massive renovation and outstanding new features.

    • $1,010$2,914 / night
    • Pool
    • Fortland's Point Photo
    • Fortland's Point Discovery Bay
    • 7 BR
      7.5 BA
    • On a stunning promontory, once the site of an old stone fort, sits a remarkable new home named Fortlands Point.

    • $2,000$3,929 / night
    • beachfront Pool
    • Harmony Hill at Tryall Photo
    • Harmony Hill at Tryall Tryall
    • 7 BR
      7.5 BA
    • 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.

    • $1,688$4,610 / night
    • Pool
    • Hummingbird House at Tryall Photo
    • Hummingbird House at Tryall Montego Bay
    • 7 BR
      7.5 BA
    • Hummingbird House, a Premier Villa, has recently undergone a two year renovation and expansion to now become one of the finest properties within the Tryall Club!

    • $1,623$5,195 / night
    • Pool
    • Longview Manor at Round Hill Photo
    • Longview Manor at Round Hill Montego Bay
    • 7 BR
      7 BA
    • On lush acres of beautifully landscaped and terraced grounds atop posh Round Hill, Longview Manor commands sweeping views of the Caribbean Sea and blue-green mountain range.

    • $1,786$4,786 / night
    • Pool
    • Phoenix at Tryall Photo
    • Phoenix at Tryall Tryall 1
    • 7 BR
      7.5 BA
    • Phoenix sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay.

    • $1,299$2,857 / night
    • beachfront Pool
    • Round House at Tryall Photo
    • Round House at Tryall Tryall
    • 7 BR
    • Round House is arresting both in its design and superb location.

    • $1,558$3,247 / night
    • Pool
    • Sugar Hill at Tryall Photo
    • Sugar Hill at Tryall Tryall
    • 7 BR
    • Sugar Hill is an elegant new 7-bedroom island home privately perched atop a manicured 3-acre property overlooking the breathtaking Caribbean Sea and exclusive Tryall Club.

    • $1,948$4,610 / night
    • Pool
    • Twin Palms at Tryall Photo
    • Twin Palms at Tryall Tryall
    • 7 BR
    • Twin Palms is perhaps the most amazing feat of architecture and design achieved in the Caribbean in decades.

    • $2,597$5,195 / night
    • Pool
    • Villas at Half Moon, A RockResort Photo
    • 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.

    • $1,200$4,500 / night 2 Specials
    • Pool
    • Whispering Waters on the Beach Photo
    • Whispering Waters on the Beach Discovery Bay
    • 7 BR
      7 BA
    • From the homeowner who created the wonderful villa Keela Wee comes its new sister house, Whispering Waters. Located immediately next door to Keela Wee, this brand new villa offers seven bedrooms and en-suite bathrooms.

    • $2,000$4,286 / night
    • beachfront Pool
    • Anticipation at Tryall Photo
    • Anticipation at Tryall Tryall
    • 6 BR
      6 BA
    • Newly reconstructed, Anticipation was named the 2012 Tryall Club Villa of the Year.

    • $1,299$3,896 / night
    • Pool
    • Bambu Photo
    • Bambu Montego Bay
    • 6 BR
      6 BA
    • Nine miles west of Montego Bay is a large private site overlooking perhaps the most glorious view of sea and sky on Jamaica’s renowned north coast.

    • $1,179$3,000 / night 1 Special
    • Pool
    • Bumpers Nest at Tryall Photo
    • Bumpers Nest at Tryall Tryall
    • 6 BR
      4.5 BA
    • On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut.

    • $1,299$3,896 / night
    • Pool
    • Endless Summer Photo
    • Endless Summer Montego Bay
    • 6 BR
      6 BA
    • One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea.

    • $1,143$2,921 / night 1 Special
    • Pool
    • Flower Hill Photo
    • Flower Hill Montego Bay
    • 6 BR
      14 BA
    • Flower Hill is one of the newest villas in Montego Bay's, Spring Farm neighborhood. This Premier 19,000-sq-ft villa sits on 4 beautifully landscaped acres overlooking the Half Moon Beach Resort and Golf Club.

    • See Rate Sheet
    • Pool
    • Following Seas at Tryall Photo
    • Following Seas at Tryall Tryall
    • 6 BR
      6 BA
    • Following Seas is a marvelous private villa with the top rating of Premier. It is tastefully renovated with thoughtful comforts, amenities and stylish new bathrooms throughout.

    • $1,299$3,896 / night
    • Pool
    • Greatview Photo
    • Greatview Montego Bay
    • 6 BR
      7.5 BA
    • Greatview is one of the most glamorous private homes overlooking the Half Moon golf course and vast ocean vista.

    • $1,371$3,857 / night
    • Pool
    • Hidden Bay by the Sea Photo
    • Hidden Bay by the Sea Runaway Bay
    • 6 BR
      6.5 BA
    • HIDDEN BAY by the SEA perches dramatically on one of the most remarkable sites on Jamaica’s renowned North Coast. Completed in 2014, the property captures both the drama of an extraordinary elevated panorama of blue sea and the proximity of its own sandy beach. Its well-planned design attracts groups of up to 12 adults and especially two- and three- generation families.

    • $1,143$3,286 / night
    • beachfront Pool
    • Jubilation at Tryall Photo
    • Jubilation at Tryall Tryall
    • 6 BR
      6.5 BA
    • Jubilation Villa is the latest reason to enjoy your Jamaican vacation at The Tryall Club. This newly created tropical paradise is elegantly furnished throughout with carefully selected antique treasures, locally built mahogany four poster beds and uniquely crafted local wood carvings.

    • $2,078$4,545 / night
    • Pool
    • Karma Bay at Tryall Photo
    • Karma Bay at Tryall Montego Bay
    • 6 BR
      6.5 BA
    • 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.

    • $1,299$3,896 / night
    • beachfront Pool
    • Keela Wee on the Beach Photo
    • Keela Wee on the Beach Discovery Bay 1
    • 6 BR
      6.5 BA
    • Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water ~ Discovery Bay.

    • $1,714$3,715 / night
    • beachfront Pool
    • Makana on the Beach Photo
    • Makana on the Beach Discovery Bay 1
    • 6 BR
      6.5 BA
    • Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay.

    • $1,857$3,715 / night
    • beachfront Pool
    • Malatai on the Beach Photo
    • Malatai on the Beach Ocho Rios
    • 6 BR
      6.5 BA
    • Just off the main road into Ocho Rios, a small lane leads to a tropical woodland. At the end of the lane, an electronic gate opens to reveal a large and magnificent villa named Malatai.

    • $1,714$3,429 / night
    • beachfront Pool
    • Mullion Cove Photo
    • Mullion Cove Bluefields Bay
    • 6 BR
      4 BA
    • Mullion Cove sets the tone and is the original prototype for the Bluefields Bay villas helping them become one of the top luxury resorts in the Caribbean.

    • $725$1,400 / night
    • Waterfront Pool
    • Pimento Hill Photo
    • Pimento Hill Montego Bay
    • 6 BR
      6.5 BA
    • Pimento Hill is a spacious private home with a legendary history. The villa overlooks the Caribbean Sea and is located just five minutes from chic Round Hill where guests enjoy complimentary membership.

    • $643$2,700 / night
    • Pool
    • Rose Cottage at Tryall Photo
    • Rose Cottage at Tryall Tryall
    • 6 BR
      7 BA
    • Rose Cottage, a six-bedroom villa, sits quietly yet dramatically on a plateau affording exceptional mountain and ocean views.

    • $1,948$3,896 / night
    • Pool
    • San Michele Photo
    • San Michele Bluefields Bay
    • 6 BR
      6 BA
    • This authentic home sits on the Caribbean with wraparound natural vistas of mountains and sea.

    • $940$1,900 / night
    • Waterfront Pool
    • Sea Island Photo
    • Sea Island Montego Bay
    • 6 BR
      6.5 BA
    • Drive through the impressive entrance gates with their tall stone columns to enter this unique and lovely home, beloved by the families who return year after year.

    • $571$2,000 / night
    • Pool
    • Six Bedroom Villa at Round Hill Hotel & Villas Photo
    • Six Bedroom Villa at Round Hill Hotel & Villas Montego Bay
    • 6 BR
    • The exquisite Caribbean villas at Round Hill are beautifully decorated by individual owners to Round Hill's exceptional standards. Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica.

    • $4,679$9,266 / night 2 Specials
    • Pool
    • Sweet Spot at the Beach Photo
    • Sweet Spot at the Beach Runaway Bay
    • 6 BR
      6 BA
    • Located on a wide sandy beach, Sweet Spot is like a pretty jewel box next to the sea.

    • $1,214$3,286 / night
    • beachfront Pool
    • Tranquillity on the Beach Photo
    • Tranquillity on the Beach Montego Bay
    • 6 BR
      6 BA
    • True to its name, Tranquillity is a place for relaxing into the calm ambiance of an exquisite home on a beautiful beachfront site ~ while being gently pampered by a competent staff.

    • $814$2,815 / night
    • beachfront Pool
    • Viviana at Tryall Photo
    • Viviana at Tryall Tryall
    • 6 BR
      7.5 BA
    • On a remarkable six private acres on a plum site at the prestigious Tryall Club, Viviana is distinguished by the top rank of Premier.

    • $1,299$3,896 / night
    • Pool
    • Windrush at Tryall Photo
    • Windrush at Tryall Montego Bay
    • 6 BR
      6.5 BA
    • Windrush overlooks the manicured Tryall Club golf course and the Caribbean Sea. Large and quite well-decorated, this fine private home is distinguished by antiques, original art and extraordinary comfort. The panoramic view of the sea is breathtaking.

    • $1,558$3,896 / night
    • Pool
    • Windward at Tryall Photo
    • Windward at Tryall Tryall
    • 6 BR
      6 BA
    • Windward at Tryall in Montego Bay is just right for a family or group of friends.

    • $1,623$3,896 / night
    • Pool

4–5 Bedroom Jamaica Villas

    • Allamanda Photo
    • Allamanda Montego Bay
    • 5 BR
      5 BA
    • Brand New 8,000-square-foot private villa on 2 acres ... perfect for families!

    • $1,286$3,000 / night
    • Pool
    • Bougainvillea at Tryall Photo
    • Bougainvillea at Tryall Tryall
    • 5 BR
      6 BA
    • Completed in January 2008, Bougainvillea is one of the most stylish homes in this collection.

    • $1,558$3,896 / night
    • Pool
    • Cielo at Tryall Photo
    • Cielo at Tryall Tryall
    • 5 BR
      5.5 BA
    • Cielo means "sky" and "heaven" and the name tells a lot about living in this wonderful villa on a hill. Add the all-day panorama of blue Caribbean Sea at every glance and "heaven" gets even better!

    • $786$2,500 / night
    • Pool
    • Cliffside Cottage Photo
    • Cliffside Cottage Montego Bay
    • 5 BR
      5 BA
    • Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.

    • $714$1,786 / night
    • Pool
    • Coconut Cottage Photo
    • Coconut Cottage Montego Bay
    • 5 BR
      5.5 BA
    • Coconut is a very private 5-bedroom cottage nestled into an acre on a gentle hillside that was the original 500-acre plantation of Round Hill Estate.

    • $643$1,500 / night
    • Pool
    • Coral Cove Villa on the Beach Photo
    • Coral Cove Villa on the Beach Discovery Bay
    • 5 BR
      5 BA
    • A recent renovation has created a second floor, fifth bedroom and updated interiors ~ all without compromising this villa's comfy put-your-feet-up signature. The feeling is an at-home, informal, relaxed lifestyle.

    • $571$1,715 / night
    • beachfront Pool
    • Drambuie Estate Photo
    • Drambuie Estate Montego Bay
    • 5 BR
      5.5 BA
    • Built in the 1940‘s by the Duke of Marlborough, Drambuie Estate is a slice of old Jamaica when lively drawing room conversation and gracious service ruled the day in an extraordinary private setting.

    • $707$1,858 / night
    • Pool
    • Elysian Plain at Tryall Photo
    • Elysian Plain at Tryall Tryall
    • 5 BR
    • Aptly named "Elysian Plain", the resting place of the Greek Gods, this spacious, 5 bedroom villa sits literally at the edge of the clear, blue Caribbean Sea.

    • $1,000$2,500 / night
    • Pool
    • Emerald Seas Photo
    • Emerald Seas Ocho Rios
    • 5 BR
      5 BA
    • Emerald Seas is an elegant two-level private home built into a mountainside beside the blue-green Caribbean Sea.

    • $643$2,000 / night
    • Waterfront Pool
    • Five Bedroom Villa at Round Hill Hotel & Villas Photo
    • Five Bedroom Villa at Round Hill Hotel & Villas Montego Bay
    • 5 BR
    • The exquisite Caribbean villas at Round Hill are beautifully decorated by individual owners to Round Hill's exceptional standards. Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica.

    • $3,449$6,849 / night 2 Specials
    • Pool
    • Great River House Photo
    • Great River House Montego Bay
    • 5 BR
      5.5 BA
    • Set on five acres of gently sloping land with sea view and surrounded by manicured lawns, today's Great River House is the product of a massive renovation in 2008.

    • $1,000$3,143 / night
    • Pool
    • Ian Fleming Villa at Goldeneye Photo
    • Ian Fleming Villa at Goldeneye Oracabessa
    • 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.

    • $2,500$8,500 / night 3 Specials
    • beachfront Pool
    • Infinity at Tryall Photo
    • Infinity at Tryall Tryall
    • 5 BR
      5 BA
    • Among the newest Premier villas at the renowned Tryall Club, Infinity is a halcyon haven overlooking the Caribbean Sea.

    • $1,753$3,571 / night
    • Pool
    • Kenyan Sunset Golf Villa Photo
    • Kenyan Sunset Golf Villa Montego Bay
    • 5 BR
      7 BA
    • Glamorous 8,000-square-foot 5-bedroom private golf villa on 2 acres with separate 2-bedroom guest cottage!

    • $1,014$2,500 / night
    • Pool
    • Knockando at Round Hill Photo
    • Knockando at Round Hill Round Hill
    • 5 BR
      6 BA
    • More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill.

    • $1,284$3,621 / night
    • Pool
    • Lime Acre Photo
    • Lime Acre Whitehouse
    • 5 BR
    • Take a step back in time. Welcome to Lime-Acre Villa, a 5 bedroom villa that sits on the South Coast among the untouched beauty of the Jamaica of years gone by.

    • $929$1,500 / night
    • Pool
    • Lolita at Tryall Photo
    • Lolita at Tryall Tryall
    • 5 BR
      5 BA
    • Lolita is a remarkable architectural achievement: a 14,500-square-foot modern villa on a four-acre site chosen for its breathtaking view of the deep blue Caribbean Sea!

    • $1,299$3,247 / night
    • Pool
    • Mahogany Hill at Tryall Photo
    • Mahogany Hill at Tryall Tryall 2
    • 5 BR
      5.5 BA
    • On seven acres overlooking the Tryall golf course and the Caribbean Sea, Mahogany Hill is among the most beautiful and spacious private homes at the Tryall Club. The unique architecture has situated all bedrooms for maximum privacy.

    • $1,065$3,896 / night
    • Pool
    • Noble House on the Beach Photo
    • Noble House on the Beach Montego Bay
    • 5 BR
      6.5 BA
    • A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean.

    • $893$2,843 / night
    • beachfront Pool
    • Nutmeg Photo
    • Nutmeg Montego Bay
    • 5 BR
      5 BA
    • A charming 5 bedroom villa in the upscale residential neighborhood of Spring Farm ~ just five minutes from three world-class golf courses, designer shops, bars, restaurants and beaches.

    • $929$2,357 / night
    • Pool
    • Overlook at Tryall Photo
    • Overlook at Tryall Tryall
    • 5 BR
      5 BA
    • Built on one of the prime sites at Tryall and conveniently located in easy walking distance of the Great House, gym and tennis courts, with total privacy and magnificent landscaping.

    • $1,299$3,247 / night
    • Pool
    • Pavilion Photo
    • Pavilion Montego Bay
    • 5 BR
      5.5 BA
    • 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.

    • $714$2,072 / night
    • Pool
    • Pineapple House at Tryall Photo
    • Pineapple House at Tryall Tryall
    • 5 BR
      5.5 BA
    • 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

    • $1,558$3,247 / night
    • Pool
    • Point of View at Tryall Photo
    • Point of View at Tryall Tryall
    • 5 BR
      5 BA
    • Located on the highest point at the renowned Tryall Club, Point of View sits on one of the most spectacular sites in the Caribbean … indeed, in the world.

    • $1,299$3,247 / night
    • Pool
    • Scotch on the Rocks Photo
    • Scotch on the Rocks Ocho Rios 1
    • 5 BR
      5 BA
    • Scotch on the Rocks is a charming turquoise villa overlooking the Caribbean Sea.

    • $789$1,434 / night
    • Waterfront Pool
    • Sea Salt at Tryall Photo
    • Sea Salt at Tryall Tryall 1
    • 5 BR
      5.5 BA
    • Sea Salt is one of the most stylish villas in this collection.

    • $1,299$3,247 / night
    • Pool
    • Sugar Bay on the Beach Photo
    • Sugar Bay on the Beach Discovery Bay 1
    • 5 BR
      5.5 BA
    • On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay.

    • $1,286$3,619 / night
    • beachfront Pool
    • Sundance at Tryall Photo
    • Sundance at Tryall Tryall 1
    • 5 BR
    • Sundance is a stunning five bedroom, traditional Palladian style villa completed in 2006,with views of the Caribbean.

    • $1,558$3,247 / night
    • Pool
    • Tek Time Photo
    • Tek Time Montego Bay
    • 5 BR
      6.5 BA
    • Tek time is Jamaican patois for advice that almost all of us need: take time to slow down and take in all that’s good and beautiful around us. Living in a glamorous villa with a staff of six who pamper their guests without ever intruding makes it easy to heed that advice.

    • $1,014$2,500 / night
    • Pool
    • Trinity at Tryall Photo
    • Trinity at Tryall Tryall
    • 5 BR
    • Completed in January of 2007, Trinity Villa is an ultra-luxurious, 5 bedroom paradise.

    • $1,818$4,091 / night
    • Pool
    • Wild Orchid Photo
    • Wild Orchid Montego Bay
    • 5 BR
      5.5 BA
    • On 220 private acres of former banana and coconut plantation stretching from mountain to sea, Wild Orchid is a glamorous and luxurious hideaway in the tropics.

    • $1,000$2,071 / night
    • Pool
    • Almond Hill Photo
    • Almond Hill Montego Bay
    • 4 BR
      4 BA
    • 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.

    • $643$1,357 / night
    • Pool
    • Avalon at Tryall Photo
    • Avalon at Tryall Tryall
    • 4 BR
      4 BA
    • Avalon is a newly decorated four-bedroom villa situated in one of the most heavenly locations at Tryall Club.

    • $786$2,071 / night
    • Pool
    • Blue Bird at Tryall Photo
    • Blue Bird at Tryall Tryall
    • 4 BR
      4 BA
    • Bluebird is located on the 2,200 acre Tryall Club. Among the most beautiful golf courses in the world, Tryall's 18 hillside and seaside fairways are accessible with in-house greens fees offered to the villa’s guests.

    • $643$1,579 / night
    • Pool
    • Calypso at Tryall Photo
    • Calypso at Tryall Tryall
    • 4 BR
      4 BA
    • Calypso is a charming open-air villa adjacent to the 16th hole of the championship Tryall golf course.

    • $451$1,623 / night
    • Pool
    • Calypso Shores Photo
    • Calypso Shores Montego Bay 2
    • 4 BR
      4 BA
    • Located in a lovely California-style residential neighborhood named Lagoons, Calypso Shores is one of the newest homes in this collection. Its prize location is a beachfront acre on a calm lagoon. Lovers of water sports will revel in this location.

    • $643$1,831 / night
    • beachfront Pool
    • Casuarina at Tryall Photo
    • Casuarina at Tryall Tryall
    • 4 BR
      4 BA
    • Casuarina is a remarkably welcoming four-bedroom villa which offers the most magical views of the Caribbean Sea from its prestigious vantage point on Barnes Hill.

    • $786$2,071 / night
    • Pool
    • Clandestino at The Caves Photo
    • Clandestino at The Caves Negril
    • 4 BR
      4 BA
    • Nestled in a lush tropical jungle within The Caves' resort property, the approximately 3,500 sq. feet wood, stone and thatched-roofed luxury Caribbean villa, Clandestino, is set on a half acre of naturally landscaped gardens, with magnificent trees, cut stone walkways, and a two-car open-air private parking area.

    • $480$2,100 / night 4 Specials
    • Waterfront Pool
    • Coo Yah at Tryall Photo
    • Coo Yah at Tryall Tryall
    • 4 BR
    • Coo Yah is a four-bedroom villa located on lush landscaping overlooking the verdant golf course and hypnotic Caribbean Sea.

    • $714$2,071 / night
    • Pool
    • Destiny Photo
    • Destiny Montego Bay
    • 4 BR
      4.5 BA
    • Destiny is a dramatic achievement of architecture and design. Its rooms stretch over 10,000 square feet of indoor-outdoor living space.

    • $1,214$2,465 / night
    • Pool
    • Eve Song at Tryall Photo
    • Eve Song at Tryall Tryall
    • 4 BR
      5 BA
    • The enchantment of Eve Song beckons vacationers from the moment they enter its driveway, lined with gorgeous trees boasting twisted trunks and beguiling greenery.

    • $643$1,579 / night
    • Pool
    • Fairwinds at Tryall Photo
    • Fairwinds at Tryall Montego Bay
    • 4 BR
      4 BA
    • Fairwinds is a beautiful four-bedroom private home with views of the golf course, sea and Montego Bay.

    • $643$1,579 / night
    • Pool
    • Four Bedroom Villa at Round Hill Hotel & Villas Photo
    • Four Bedroom Villa at Round Hill Hotel & Villas Montego Bay
    • 4 BR
    • The exquisite Caribbean villas at Round Hill are beautifully decorated by individual owners to Round Hill's exceptional standards. Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica.

    • $2,269$5,569 / night 2 Specials
    • Pool
    • Hillside Villa at Round HIll Photo
    • Hillside Villa at Round HIll Montego Bay
    • 4 BR
      4 BA
    • 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 tradewinds ... which also happened to have one of the most spectacular views in all the Caribbean.

    • $729$2,000 / night
    • Pool
    • Little Hill at Tryall Photo
    • Little Hill at Tryall Tryall
    • 4 BR
      4 BA
    • Little Hill was built in 1959 by an architect Robert Hartley. It was the first villa to be built at The Tryall Club in the Classic West Indies style around a circular 30 foot diameter swimming pool with extensive covered terraces throughout.

    • $1,299$2,597 / night
    • Pool
    • MaMoura at Tryall Photo
    • MaMoura at Tryall Tryall
    • 4 BR
      4 BA
    • This 4 bedroom villa is a wonderful example of circular and octagonal design taking full advantage of the view on all sides.

    • $643$1,579 / night
    • Pool
    • Out of the Blue Photo
    • Out of the Blue Treasure Beach
    • 4 BR
      4 BA
    • Out of the Blue is an oxymoron: a contemporary home in Old Jamaica. And what a home it is!

    • $600$825 / night
    • beachfront Pool
    • Reef House at Tryall Photo
    • Reef House at Tryall Tryall
    • 4 BR
    • You approach Reef House, a deluxe 4 bedroom villa located on the grounds of the Tryall Club, over a stepped bridge and enter into a world of serene, comfortable living.

    • $643$1,579 / night
    • Pool
    • Seaspray  at Tryall Photo
    • Seaspray at Tryall Tryall
    • 4 BR
    • This idyllic setting sets a splendid tone for invigorating days in the sun and sea.

    • $786$2,071 / night
    • Pool
    • Serenity on the Beach Photo
    • Serenity on the Beach Montego Bay
    • 4 BR
      4 BA
    • Serenity is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre 8 miles west of Montego Bay.

    • $536$2,160 / night
    • beachfront Pool
    • Seven Seas on the Beach Photo
    • Seven Seas on the Beach Ocho Rios
    • 4 BR
      4.5 BA
    • The morning sun has turned the sea and the dew on the palm trees to silver. The non-stop trade winds waft through the rooms of the villa and the aroma of fresh-baked bread works its way from the kitchen to my bedroom window.

    • $1,000$1,672 / night
    • beachfront Pool
    • Sunrise at Tryall Photo
    • Sunrise at Tryall 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.

    • $643$1,579 / night
    • Waterfront Pool
    • The Hermitage Photo
    • The Hermitage Bluefields Bay
    • 4 BR
      3.5 BA
    • Architect-designed and lauded as a prized jewel of our luxury Caribbean resorts, this distinctive home was completed in 1991.

    • $900$1,800 / night
    • Waterfront Pool
    • Tradewinds at Tryall Photo
    • Tradewinds at Tryall Tryall
    • 4 BR
      4 BA
    • This cozy home sits on two acres at the famous Tryall Club ~ directly on the Caribbean Sea. 300 feet of waterfront form the north perimeter of the property.

    • $643$1,579 / night
    • Waterfront Pool
    • Windsong Photo
    • Windsong Montego Bay
    • 4 BR
      4 BA
    • Windsong is an exquisite and very private home just minutes from Round Hill.

    • $500$1,843 / night
    • Pool
    • Yellowbird at Tryall Photo
    • Yellowbird at Tryall Tryall
    • 4 BR
      4 BA
    • Yellowbird is an excellent family home on a large, lovely landscaped site overlooking the Tryall golf course and the Caribbean Sea. The tradewinds are delightful; the view is wonderful.

    • $786$2,071 / night
    • Pool

3 Bedroom Jamaica Villas

    • Blue Heaven Photo
    • Blue Heaven Montego Bay
    • 3 BR
      2.5 BA
    • The grounds are adorned by elegant palm trees, bougainvillea, hibiscus, ginger lilies, frangipani, bamboo, ferns, lavender and periwinkle. Velvety soft zoysia grass invites barefoot walks around the lawn.

    • $457$1,000 / night
    • Pool
    • Eureka at Tryall Club Photo
    • Eureka at Tryall Club Tryall
    • 3 BR
    • Eureka is a very special retreat nestled in a private and pretty location at the end of a cul-de-sac.

    • $779$2,078 / night
    • Pool
    • Goat Hill Photo
    • Goat Hill Montego Bay
    • 3 BR
      3.5 BA
    • Goat Hill 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$2,143 / night
    • Pool
    • Island House at Tryall Photo
    • Island House at Tryall Tryall
    • 3 BR
    • The delightfully refurbished Island House remains true to the essence of its name. Beautiful touches of Jamaican craft and objets d’ art create an atmosphere which invites pleasurable relaxation.

    • $571$1,393 / night
    • Pool
    • Jus' Paradise Photo
    • Jus' Paradise Montego Bay
    • 3 BR
      5 BA
    • Jus' Paradise is an aptly-named private villa located in a gated residential area of upscale homes in the lush hills of Rose Hall.

    • $671$1,329 / night
    • Pool
    • Linga-Awile Cottage on the Beach Photo
    • Linga-Awile Cottage on the Beach Discovery Bay
    • 3 BR
      3.5 BA
    • This 3-bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove Villa, on the clear waters of Discovery Bay.

    • $400$743 / night
    • beachfront Pool
    • Linger Longer at Tryall Club Photo
    • Linger Longer at Tryall Club Tryall
    • 3 BR
      3 BA
    • Linger Longer is an exceptional three-bedroom villa with a winning view of the 13th hole of Tryall Club’s golf course and of the Caribbean Sea. A distinctive enclosed courtyard with swimming pool marks the unique entrance to this villa.

    • $649$1,818 / night
    • Pool
    • No Problem at Tryall Photo
    • No Problem at Tryall Tryall
    • 3 BR
      3 BA
    • Commanding excellent views of the Caribbean Sea and Tryall Club’s golf course, No Problem is a cozy two-storey villa.

    • $571$1,393 / night
    • Pool
    • Pinnacle at Tryall Photo
    • Pinnacle at Tryall Tryall
    • 3 BR
      3.5 BA
    • Pinnacle is a casual open-air Caribbean-style villa overlooking the historic Tryall Great House, golf course and the sea.

    • $714$1,857 / night 1 Special
    • Pool
    • Providence House Photo
    • Providence House Bluefields Bay
    • 3 BR
      3.5 BA
    • Providence House, our most recent acquisition, contains three bedrooms -- each with sensational views -- with all living spaces beautifully framing Bluefields Bay and the sunsets.

    • $535$1,200 / night
    • Waterfront Pool
    • Serenity at Tryall Photo
    • Serenity at Tryall Tryall
    • 3 BR
      4 BA
    • The three-bedroom villa Serenity sits high on Copperwood Ridge, surrounded with landscaped gardens, bright with tropical flowers.

    • $519$1,396 / night
    • Pool
    • Sunset at Tryall Photo
    • Sunset at Tryall Montego Bay
    • 3 BR
      3.5 BA
    • Sunset is a charming three-bedroom beach house on a fabulous site: a double lot absolutely on the edge of the beach and the sea.

    • $714$1,922 / night
    • beachfront Pool
    • Three Bedroom Villa at Round Hill Hotel & Villas Photo
    • Three Bedroom Villa at Round Hill Hotel & Villas Montego Bay
    • 3 BR
    • The exquisite Caribbean villas at Round Hill are beautifully decorated by individual owners to Round Hill's exceptional standards. Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica.

    • $1,939$4,339 / night 2 Specials
    • Pool
    • Vista del Mar at Tryall Photo
    • Vista del Mar at Tryall Tryall
    • 3 BR
      3 BA
    • Vista del Mar is remarkable for its magnificent view of the deep blue Caribbean Sea and peaceful, private location.

    • $1,039$2,208 / night
    • Pool

1–2 Bedroom Jamaica Villas

    • Cottonwood Cottage Photo
    • Cottonwood Cottage Bluefields Bay
    • 2 BR
      2 BA
    • Our most nature-integrated villa, this home has two bedroom suites on four beachfront acres purchased from the Jamaican government.

    • $535$1,050 / night
    • Waterfront Pool
    • La Casita Photo
    • La Casita Montego Bay
    • 2 BR
      2 BA
    • The La Casita architect and homeowner have succeeded in creating a remarkable two-bedroom villa in the stylish Spring Farm area of Rose Hall. Overlooking the sea, this is a small but luxurious villa ... with full staff and private pool.

    • $357$700 / night
    • Pool
    • Little Palm at Tryall Photo
    • Little Palm at Tryall Tryall
    • 2 BR
    • This enchanting 2 bedroom villa is built around a swimming pool and a tropical vine covered veranda and is a deluxe property within Tryall.

    • $494$1,390 / night
    • Pool
    • Milestone Cottage Photo
    • Milestone Cottage Bluefields Bay
    • 2 BR
      2 BA
    • Milestone Cottage has always been the honeymoon favorite, although also popular for small families with its two bedrooms.

    • $535$1,000 / night
    • Waterfront Pool
    • Poinciana at Tryall Club Photo
    • Poinciana at Tryall Club Tryall
    • 2 BR
    • Tryall Club’s historic Georgian Great House is the site for thirteen exquisite Great House Villa Suites.

    • $481$1,390 / night
    • Pool
    • The Cottages at Goldeneye Photo
    • The Cottages at Goldeneye Oracabessa
    • 2 BR
    • GoldenEye overlooks the Caribbean Sea in the quiet village of Oracabessa Bay on Jamaica’s north coast.

    • $975$2,200 / night 4 Specials
    • Pool
    • Two Bedroom Villa at Round Hill Hotel & Villas Photo
    • Two Bedroom Villa at Round Hill Hotel & Villas Montego Bay
    • 2 BR
    • The exquisite Caribbean villas at Round Hill are beautifully decorated by individual owners to Round Hill's exceptional standards. Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica.

    • $1,046$4,071 / night 2 Specials
    • Pool
    • Mirador at Tryall Photo
    • Mirador at Tryall Tryall
    • 1 BR
      2 BA
    • Mirador is a stylish one-bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course.

    • $357$929 / night
    • Pool

More About Jamaica Villa Rentals

Our villas range in size, from cozy private villas perfect for two, to expansive villa estates that can easily accommodate an extended family of twenty. In addition to the luxury of space, the villas also offer other amenities. Each Jamaica villa has its own personal cook, so guests can savor authentic Jamaican cuisine like jerk chicken or enjoy their own favorite dishes prepared daily. Daily maid service is also available at each villa.

Some of the Jamaica villas in our collection also offer guests access to the island's wonderful resorts such as Round Hill, The Palmyra Resort & Spa, Doctor’s Cave Bathing Club, and Tryall Club. Round Hill’s and The Palmyra’s facilities include a spa, fitness center, and a myriad of water sports. Doctor’s Cave Bathing Club is one of the most famous beach clubs in Jamaica.  And the Tryall Club has a well known, 18-hole, par-72 championship course designed by Ralph Plummer, hobie cat and sunfish sailing, its own private beach, tennis courts, and a spa and gym.

While many people venture to Jamaica to sunbathe on its lovely beaches, the island also has much more to offer--especially for those looking for a little more activity. Golfers have their pick of Jamaica’s well-known golf courses, considered by many to be the best in the Caribbean. Windsurfers, scuba divers, and deep-sea fisherman will find plenty to do in Jamaica's blue waters. Hikers and horseback riders will discover numerous trails to explore. Sightseers will want to climb the slippery steps of the famous 600-foot-high Dunn's River Falls, take a train tour of the island, or enjoy a gentle river rafting trip on the Murtha Brae River.

Jamaica is also a great vacation destination for families. There are plenty of water sports to keep teens busy, while the gentle waters and sandy beaches keep younger children occupied. Children will love bird watching at Rocklands Feeding Station, home to Jamaica's 27 native species. And many of our villas offer kids club membership at the resorts.

Browse through our luxury selection of the most sought-after villas and vacation homes on Jamaica. Call today to plan your villa getaway at 800.832.2302.

 

tags, as close as possible to the opening tag. Creation Date: 05/25/2012 -->