Great Deal on Villas: Stay for 7 ~ Pay for 5!
Please Inquire for Details
only certain properties


Villa, Condos & Resorts - Montego Bay, Jamaica
Ocean Front Small Ocean View Large Ocean View Resorts & Hotels SuperClubs All Inclusive

Pamper Yourelf! Cindy Wimsatt is a Certified Massage Therapist and she will come to your villa


Choose a Villa
Montego Bay is Jamaica's second largest city of around 100,000 inhabitants. It dates from about 1494. Now it is one of the most colorful and vibrant of all the Caribbean cities, virtually brimming with activities you will enjoy and remember forever. Enjoy a day at Croydon Plantation, an afternoon Mountain Valley rafting and then catch a magnificent sunset on the water with a relaxing evening sail and dinner. Montego Bay offers it all from a quiet day on famous Doctor's Cave beach or an exhilarating sail on a catamaran with snorkleing, to delightful evenings filled with the beat of Reggae and Calypso. A favorite of the younger crowd is Margaritaville, right on the Hip Strip. The villas are situated in a quiet, residential areas, yet only minutes away from downtown, championship golf courses, and the airport. Swim in your own freshwater pool and be delighted by a meal of your choice, prepared by your own cook. Your housekeeper will gladly arrange to baby sit your children or provide laundry services. You are ideally situated for exploring the island. Negril and its 7 mile beach is an hours drive away. Ocho Rios and Dunn's River Falls is a couple of hours to the east.

Ocean Front Ocean View Villas  /  Resorts
Lagoon
Villa from the sea Calypso Shores
Private Beach, Private Pool, 4 Bedroom Luxury Villa in Gated Community with gorgeous views. Full staff to pamper, top notch amenities such as LCD flat screen TVs, WiFi Internet, Gourmet Kitchen, Hobie Cat sailboat and 2 sea kayaks plus snorkelling gear so you could never get bored!
Afimi
Spectacular, new villa in the gated Lagoon neighborhood. Private, white sand beach, infinity pool, community gym, tennis courts and you are just 10 minutes from the airport.
Tryall
Pool Tradewinds - Tryall
4 Bedrooms, 4 Bathrooms (4 Ensuite), Beachfront, Pool, Tradewinds sits right on the shore of the Caribbean. As soon as you walk through the front door, you get your first view of the sea, and almost every room in the villa takes full advantage of its magnificent coastal view. The beautifully appointed living room is connected to a formal dining room and two outdoor terraces, ideal for alfresco meals by the water's edge. The master bedroom and two guest rooms are in the main house. The fourth bedroom is in a charming seaside cottage next to the pool. All the bedrooms have en-suite bathrooms.
Reading Bay
Noble House
You cannot find a more elegant, luxurious villa pretty much anywhere in the Caribbean. With 15,000 ft² of indoor and outdoor living space and situated on 5 acres of beach front land, you will be able to unfold as you please. The professional staff is there to take care of all your needs so that you may absorb the gentle breezes coming off the private beach or drink in the tropical beauty of the exotic gardens or reflection ponds that are all around the property. Noble House is the kind of place that you should stay in at least once...but we know you will want to keep on coming back.
Pool and Ocean view Serenity
Sister villa to Tranquillity, next door. Both are deluxe beach front villas in Montego Bay. Serenity is a Three Bed/Three Bath with A/C in the bedrooms, full staff, shared tennis court.
Pool Tranquillity
Sister villa to Serenity, next door, Tranquillity matches the luxury and ambience. With four bedrooms and a one bedroom beach front cottage, Tranquillity is ideal for the large family or group of friends.
Pool Wharf House
Imagine a 300-year-old cluster of hand-hewn stone buildings next to the sea. Gun slots in 18-inch stone walls conjure a tale of soldiers defending the wharf and its sugar trade from Caribbean pirates and foreign invaders. That is Wharf House. Naturally it is brought up to date with all the amenities one expects in the 21st century.
Mahoe Bay
Villa Leeward
Three bedroom, Ocean Front with private beach and fresh water pool, full staff to pamper you and in Montego Bay. Right next to Villa Windward on peaceful Mahoe Bay. Close to everything you want. Does it get better than this?
Villa Windward
3 bedrooms, 3 baths upstairs. Downstairs are the living and dining areas, grand veranda, large freshwater swimming pool and a private white sand beach. There is a staff of four: cook, chambermaid, gardener and a security guard. Three championship golf courses are all within one mile. Excellent facilities for tennis, fishing, horseback riding, scuba diving, parasailing are all close by.
Ocean View
3 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Blue Heaven
A 3 Bedroom villa perched on a peaceful hill, Blue Heaven is named for its breathtaking panorama of the sea and its calm, relaxing ambiance. Tradewinds waft through the rooms while the sweet and gracious staff relieve guests of virtually all responsibility. 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.
Eureka
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. Complimentary shuttles transport guests from the villa's front door to all locations within the resort. Tryall offers a beauty salon offering massages and reflexology treatments, a large swimming pool at the Great House and a white sand private beach. Spend days on the sunny beach while waiters serve you from the beach bar. Snorkeling, kayaking, hobie cat sailing and sunfish sailing are complimentary.
Leaford Leaford
SPECIAL - Up to 40% Off - Starting From $1250

Resting within 2 acres of fruit and palm trees and with an impressive, panoramic view of the Caribbean, Villa Leaford is a 3 bedroom, 3 bath villa that comes with a professional chef, housekeeper and a butler to cater to all of your needs.
Seafore - Tryall
Seafore is a beautiful villa features a wonderful octagonal swimming pool with an extended side for lap swimming and a convenient poolside wet bar for those sensational tropical drinks. The pool deck offers clear views of the 16th hole and fairway.
Vista del Mar
An alley of palms leads up to Vista Del Mar, at the top of Tryall. Aptly named, this magnificent villa commands a breathtaking view over the rolling greens of the property's famous golf course and glittering Caribbean Sea. The entrance hall opens on to 40' x 40' living room and 40' x 30' covered porch facing a terrace and pool, all with panoramic vistas, four bedroom-suites with luxurious bathrooms and walk-in closets face the ocean. A dining pavilion, with lovely views on all three sides.
4 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Almond Hill
Almond Hill is a lovely, new private, 3 bedroom villa surrounded by a 500-acre coconut plantation with a large private pool. The villa and grounds were designed by Prince Kasimir Korybut in 1993.
Calypso - Tryall
Set in 4 acres of exquisite gardens and orchards, Calypso is a charming and tranquil home located above the famous Tryall Golf Club's 16th green, with views to the ocean. A stay here comes with the privileges of luxury villa living, the amenities of a resort and the privacy of an exclusive club.
Fairwinds - Tryall
A beautiful four-bedroom, private home with a magnificent sea view. Meticulous attention to design and comfort have resulted in a superb home away from home, Mahogany parquet floors, cable televisions and sound system, sunken Roman baths, a first-class chef plus all the amenities of the exclusive Tryall Club combine to distinguish Fairwinds as one of the truly fine vacation homes of the Caribbean.
Jamaica Columns
Set on 5 acres of beautifully manicured land, filled with all manner of fruit trees and tropical flowers and perched 150 feet above the Caribbean but just 8 kilometers east of Montego Bay Airport, Jamaica Columns is a modern great house in the true Jamaican tradition.
Villa Mawr
A comfortable four bedroom ocean view villa on an acre and a half of lush tropical gardens. All four air conditioned bedrooms are equal in size and offer a choice of king or two single beds in three of the rooms, and queen bed in the fourth. One of the two upper floor bedrooms has its own private ocean view balcony, The living area, newly decorated in blue and green fabrics with washed walls, opens onto a thirty foot long covered verandah overlooking the pool, with a magnificent ocean view.
Seaview Cottage
Comfortable, affordable four bedroom, 3 bath villa with ocean view in Rose Hall. Located across from Harvey Beach which was featured on the Travel Channel for its excellent scuba diving. Close by are four championship golf courses, fine dining restaurants, four shopping villages and the world famous Scotchies Jerk Centre.
Skylark
Skylark Villa is private and secure on 2 tropical acres of palm and fruit trees. The villa overlooks the Caribbean at Half Moon Bay. It is a 4 bedroom villa that comes with a full, live-in staff of three to ensure your vacation exceeds all your expectations.
Wind Song
An exquisite and very private 4 bedroom home just four minutes from Round Hill. You will have spectacular views day and night and the most favorable trade winds. The east view captures the sunrise and Montego Bay ~ the west, an equally lovely vista of Round Hill, the sunset and the deep blue Caribbean. Every amenity imaginable is here PLUS there is a free guest membership to Round Hill
5 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Villa Bahia
A luxurious 5 Bedroom villa with Pool, Magnificent Ocean Views, 24 Hour Service. Full staff is a given. Privacy and Lush Tropical Gardens, Just Minutes From Everything in Montego Bay. Gourmet Dining - Prepared-to-taste, savory Caribbean entrees that pique your palate. (Including twilight dining). Complimentary first meal and rum punch upon arrival.
Cliffside Cottage
You get majestic views of Montego Bay from this beautiful villa that has every conceivable amenity for your enjoyment. Prepare to be pampered by the staff.
Drambuie Estate
Cut stone walls brought from England 200 years ago as ballast comprise the 18-inch walls of the Main House. Vaulted ceilings are 16 feet high. Floors are cool tiles from England, Mexico and South America. The Main House consists of the Great Room with pool table, large screen television, VCR and sound system; inlaid games table for chess, checkers or backgammon; and comfortable sitting area. French doors open to a 330' wrap-around stone verandah furnished with al fresco dining tables, wicker sitting area, tempting hammock and lawn leading to the pool.
Greatview
A Fantastic Luxury Springfarm Villa with every amenity you can think of. Infinity edge pool, a chef who will prepare meals that will boggle your mind, High speed Internet, Physically challenged friendly property, the list goes on.
Villa Lolita
Impressive 5 bedroom villa up on a hill within the 2200 acre Tryall Golf Resort with majestic views of the Caribbean. 2 Master suites, 3 suites, 5 pools on 4 acres.
Montego Bay Villa Vacation Rental Monzon's
SPECIAL OFFER
UP TO 40% OFF REGULAR RATES
Only 7 villas are in the private community of "Content." The estate once belonged to Winston Churchill and it was his daughter that sold off parcels to create the seven estates. Drambuie is one, the Hammerstein estate is another.
Nutmeg
  Stay for 7 - Pay for 5  
COMPLIMENTARY CAR + DRIVER INCLUDED

Deluxe Villa in Spring Farm with every amenity you can think of, from High Speed WiFi to a chef. Five acres of tropical gardens flush with flowers, oranges, limes, lemons, June plum, breadfruit, grapefruit, avocado and mango. This large lawn is a wonderful playground for children.
Villa Rococo
5 Bed / 5½ Bath Deluxe Villa Overlooking MoBay & the Caribbean. Close to world class golfing, Perfect spot for a wedding, honeymoon, anniversary or romantic getaway.
Designed by Sir Winston Churchill's relative Lady Sarah Churchill in the 1950's, Villa Rococo is a world-class private home ~ remarkable for exquisite interior and exterior designs, excellent staff and services, seclusion and luxurious amenities ~ catering to all! Over the past 5 decades Villa Rococo has earned and maintains a reputation for attracting dignitaries and royalty along with a wide cross-section of individuals from around the world.

Wild Orchid
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. In true Colonial style, Wild Orchid is meticulously staffed so that guests are pampered through sunny days and relaxed evenings ... with memorable home-cooked meals served in the spacious indoor dining area or on the large open verandah under the almond trees.
BONUS - Complimentary Membership to the Round Hill Beach Club & Resort
Windrush
Located on the 2,200 acre Tryall Club and 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. 5Br, 5Ba (5 Ensuite), Pool This entirely renovated luxury villa is beautifully situated on five acres of lush gardens. It features an air-conditioned master bedroom with a four-poster Jamaican mahogany king-size bed and mahogany floors, en-suite bathroom with separate shower and dressing room. Four more guest bedrooms (two with king-size beds and two with twin beds) also have en-suite bathrooms.
6 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Anticipation - Tryall
Arguably, one of the best positioned locations at the Tryall Club, it boasts an uninterrupted 180 degree panoramic view of the Caribbean Sea. The infinity pool allows one of the best viewing locations. Newly reconstructed and combining Caribbean architecture with European style décor Anticipation is nestled at the top of the hill on Copper Ridge.
Casa de Familia
All the expected amenities and all the perks of Montego Bay. Just minutes to downtown and duty free shopping. The beach is nearby, Golf, SCUBA, Sailing you name it, you can find it in MoBay.
Bedroom Endless Summer
RECESSION DISCOUNTS
Please Inquire About This Offer
Located in Springfarm this a grand, 6 bedroom mansion. Top shelf amenities and endless views of the Caribbean. Ideal for your wedding! Complimentary Rose Hall Membership Included
Hanover House
High ceilings and small treasures from another century evoke the former grandeur and elegance of a dignified past Jamaican lifestyle.
Highland House
Located in the Great River area, overlooking Montego Bay is a 17 acre, 6 bedroom luxury villa and plantation. Once owned by Oscar Hammerstein, legend has it that he wrote the lyrics to The Sound Of Music on the terrace.
Imani Ashia
A nice sized private pool, outdoor Jacuzzi, views of the Caribbean sea, full staff of cook and housekeeper, gardener nake this a true Jamaican vacation villa.
Pimento Hill
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.
Sea Island
Dramatically renovated in 2005. It lies on 7.5 ocean view acres near Montego Bay. 6 luxurious bedrooms with private attached bathrooms and a staff of seven ensure that your vacation will be a very memorable one.
Complimentary Membership to Round Hill Beach Club and Resort included.
Summertime
Nestled on 5 acres, perched on a hillside with gorgeous views of Montego Bay and the Caribbean. With 6 bedrooms, full staff, pool with fountain, pool side bar, complimentary driver with van, exercise gym with all types of equipment and even a putting green, there is no excuse to not take friends and family here.
Wheel House - Tryall
This beautiful villa is in the lush 2,200-acre Tryall Club on the quiet, pristine north coast of Jamaica. Tryall features a championship golf course, state-of-the-art tennis center and a pristine, white sand beach.
Wuthering Heights
Just minutes from Golf, beaches and Rose Hall and also exclusive to Sunny Villa Holidays you would be hard pressed to find a better six bedroom six bathroom villa in Jamaica. It has all the features that one expects in Jamaica, such as full staff, pool, TV in all rooms and fresh fruits direct from your garden. And guess what! The rates are great as well.
7 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Pool & Gazebo Belle Abri
Just finished in 2006, was built with meticulous attention to quality in every detail. To mention but a few of the top-notch amenities in Bell Abri, you will find: Pool table, High speed Internet, free calls to the USA, infinity edge pool, fully equipped exercise room, media room with 42" plasma TV on cable, 2 complimentary cell phones during your stay...and on and on
Fairway Manor
This villa rents as private villa or B & B. All Inclusive Option Available. Overlooking Half Moon Bay. Complimentary membership at the Four Star Deluxe Wyndham Rose Hall Resort & Country Club included. Less than 5 min from 4 championship golf courses: Ritz, Half Moon, Wyndham and Ironshore. Internet Access Available.
Pink Hibiscus Pink Hibiscus
A 7 bedroom / 7 en-suite bathrooms Ironshore villa on an acre of tropical garden. The pool is large and 9 feet deep. This villa also comes with a 12 passenger van and driver for your convenience. Great Rates .. from US$ 68 per room per day.
Sol de Caribbean
12,000 ft² mansion in Spring Farm overlooking Half Moon Resort. Just 5 minutes from the Ritz-Carlton and numerous golf courses, such as Rose Hall and only 15 minutes from downtown Montego Bay. Gorgeous villa and stunning views.
Thomas House
Seen in the John Candy movie "Cool Runnings" about the Jamaican Olympic bobsled team, Thomas House offers Hollywood style accommodations. Overlooking the first fairway of the fabulous Half Moon golf course on three acres of lawn and gardens outside Montego Bay. It is ideal for families or large gatherings, and is the perfect villa for weddings.
8 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Boca del Rio
On a hill overlooking Montego Bay in the Great River area. With 8 bedrooms it is ideal large families, groups and small weddings. Naturally, there is full staff on hand and you are just minutes from downtown Mo Bay.
9 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Dream Castle Villa Dream Castle Villa
A luxury villa in the Ironshore area of Montego Bay, and overlooking the golf course there, is a luxury villa with a staff that is dedicated to you and your vacation. It caters to professionals that appreciate the finer life. There are six bedrooms, and full wedding and business meeting facilities available.
Summerhill Villa
One of the newest villas in the Springfarm area, is a 10,000 sq. ft, brightly painted three story elegant, yet charming, romantic and comfortable nine bedroom private villa. Summerhill is surrounded in lush tropical flowers, fruit trees, a massive well manicured lawn, walking paths and a garden sitting area designed for meditating, moments of privacy or a garden wedding ceremony.
Hunters Villa
Located in the Ironshore area of Montego Bay, just a few minutes away from the airport. Shopping is down the road at the Blue diamond shopping center, There are restaurants, pharmacy and a cinema in the shopping mall as well.
Seaview Chateau
SPECIAL DISCOUNTS
Please Inquire

Another Great 9 bedroom villa in Ironshore, all with en-suite baths and a wonderful Honeymoon Suite with jacuzzi as well.Sea View Chateau that is more than ideal for a wedding or a family reunion or whatever else you may decide. As with every villa in Ironshore, you are in the thick of things. Downtown with all the night life and duty free shopping is just a few minutes away. You are even closer to the airport which means no long drives before you vacation starts in earnest.
10 Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Silent Waters
Located 6 miles west of Montego Bay on the North Coast Road, on one of the highest mountaintops overlooking Montego Bay and the Caribbean Sea, Silent Waters is on 18 acres of lush tropical vegetation. Twelve buildings, helicopter pad and tennis court occupy five of the acres. There are five villa suites (9 air conditioned bedrooms) to accommodate as many as 18 guests. Each bedroom is equipped with a radio, CD player, TV, and DVD/VCR systems. Addition of the owner's private villa (1 air conditioned bedroom) enables 20 guests.
11+ Bedrooms  Bedrooms:   3  4  5  6  7  8  9  10  11+  Ocean Front
Villa Kenwood
is an 11 bedroom villa in the Ironshore neighborhood. Built on two levels, it affords roominess yet privacy. It is close to downtown, the airport and is within walking distance to shopping and entertainment.
11 bedroom ocean view villa Woodscape Villa
An Ironshore villa that offers luxury accommodation, a large tropical garden with unlimited parking space. Your comfort is assured in our high quality furnished rooms (11) which comprises double ensuite, twin rooms with private bathroom. All rooms include a color television, tea/ coffee making facilities, air condition, a safe for keeping your personal possessions and a variety of surprising little extras.
Resorts Ocean Front Villas  /   Ocean View Villas
**************************
Every 3rd Night Free!
**************************

Coyaba Resort & Beach Club is an intimate, 50 room property with a quiet blend of understated elegance and old-world feel.
Half Moon
Surround yourself in luxury, and let your senses soar at Half Moon Resort. One of the oldest and most luxurious resorts on the island. They have the years of experience to ensure your stay is perfect
SuperClubs All Inclusives

SuperClubs - Worlds Best All Inclusives
Click for SuperClubs

Sunny Villa Holidays Mail OR

Phone Numbers & Office Hours
  USA: (815) 308-7604  •  Canada: (416) 848-6049 / (204) 480-1502  •  UK: 0844 979 5907  
  Office Hours: Mon - Fri: 9:00 A.M - 8:00 P.M. EST  •  Sat: 9:00 A.M. - 6:00 P.M. EST  •  Sun: TRY US