Vacation Rentals By Owner In Montego Bay, SJ

$2028.45

Modern 4BR Hillside Villa | Pool & Beach Club Access

Montego Bay, Saint James, Jamaica

Summary:brbrThe Vacation Haven is a sophisticated four-bedroom villa nestled in the tranquil hills of Rose Hall, Montego Bay, Jamaica. Surrounded by lush greenery and ocean views, this private villa blends open-plan living with vibrant Jamaican design, offering sun-soaked terraces, panoramic views of both sea and mountains, and an inviting pool deck with a bar and grill area. Ideal for families, groups, or celebrations, The Vacation Haven delivers a flexible, tailored Caribbean escape with space for up to 12 guests.brbrbrbrThe Space:brbrDesigned around open living and seamless indoor-outdoor flow, The Vacation Haven’s contemporary spaces capture breezes and views at every turn. The spacious living and dining area opens to the outdoors with expansive sea views, creating a relaxed yet vibrant atmosphere for gathering and entertaining.brbrbrbrThe villa accommodates four very spacious bedrooms, each with its own ensuite bathroom and generous views of the ocean or surrounding mountains. Comfortable layouts and thoughtful furnishings ensure privacy and rest for every guest, while the large pool deck, outdoor bar, grill area, and pool chaises make the exterior just as inviting as the interior.brbrbrbrGuest Access:brbrGuests enjoy exclusive access to The Vacation Haven and its grounds, including indoor living spaces, outdoor terraces, gardens, and the private pool with bar and grill area.brbrbrbrAs part of your stay, guests also enjoy complimentary resort membership benefits at the Rose Hall Beach Club, subject to availability and club policies. This includes access to the beach, pool facilities, and shared amenities at the beachfront club. Additional services and experiences such as watersports, spa treatments, food and beverage offerings, and tennis may be available through the club for a fee and are subject to availability and club terms.brbrbrbrPlease note that access to beach club amenities and services is governed by club policies and availability. On occasion, facilities and guest services may be unavailable due to private events. The Rose Hall Beach Club reserves the right to modify or update its membership benefits without prior notice.brbrbrbrThe Neighborhood:brbrThe Vacation Haven is located in the prestigious Rose Hall community of Montego Bay, a serene residential enclave known for its historic charm, championship golf courses, and neat coastal views. The area offers easy access to beaches, local attractions, and vibrant Jamaican culture, while providing a peaceful retreat away from the busiest resort centres.brbrbrbrNearby, world-class golf, seaside dining, and attractions such as the Rose Hall Great House add distinctive experiences to your stay. The villa’s hillside setting also means scenic morning light and refreshing breezes throughout the day.brbrbrbrGetting Around:brbrWhether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape.brbrbrbrOther Things to Note:brbrThe Vacation Haven includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. brbrbrbrGratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team.brbrbrbrBeyond just a stay, The Vacation Haven offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.brbrbrbrInteraction with Guests:brbrOur Caribbean Villa Escapes team is available before arrival and throughout your stay to assist with planning, recommendations, and personalized arrangements. While your privacy is always respected, support is always within reach.brbrbrbrRelax and settle in knowing your on-site villa team is available throughout your stay to ensure your comfort. For additional assistance at any point during your stay, our guest app, Privé by CVE, allows you to connect easily with our team, ensuring thoughtful support is always at your fingertips.

4

Bed

4

Bath

12

Sleeps

$2649.54

/ Nightly

Villa

Sprawling 7BR Villa Overlooking the Sea | Pool, Hot Tub & Resort Access

Montego Bay, Saint James, Jamaica

Summary:brbrEndless Summer is a grand seven-bedroom villa perched hillside in the prestigious Spring Farm area of Montego Bay. Set high above the coastline, this expansive private estate offers sweeping views across the championship Half Moon Golf Course and the Caribbean Sea beyond. Designed for relaxed luxury and effortless entertaining, Endless Summer is ideal for multi-generational families, group getaways, and special celebrations seeking space, privacy, and exceptional service.brbrbrbrThe Space:brbrEndless Summer spans approximately 11,000 square feet and welcomes guests through a dramatic entrance into elegant, light-filled living spaces. Formal and casual lounges flow seamlessly onto deep verandas and outdoor terraces, creating a natural connection between indoor comfort and the surrounding landscape.brbrbrbrThe villa features seven well-appointed bedrooms, each with an ensuite bathroom, comfortably accommodating up to fourteen guests. Bedrooms are thoughtfully arranged to provide privacy while maintaining easy access to shared living areas, making the home well-suited for both large gatherings and quiet moments of retreat.brbrbrbrOutdoor living is a highlight, with a generous pool and terrace overlooking the golf course and sea beyond. Lush gardens, open lawns, and multiple seating areas create inviting spaces for morning coffee, sunset cocktails, and evenings under the stars.brbrbrbrGuest Access:brbrGuests enjoy exclusive access to Endless Summer and its grounds, including indoor living areas, wraparound verandas, outdoor terraces, landscaped gardens, and the private pool and hot tub.brbrbrbrAs part of your stay, guests also enjoy complimentary resort membership benefits at the Half Moon Beach Club, subject to availability and resort policies. Included access features Eclipse Beach, the Jacuzzi, tennis courts, fitness center, croquet lawn, and a miniature putting green. Additional experiences such as spa services, horseback riding, watersports, and tennis instruction may be arranged on the day of service and are subject to availability and applicable fees. While tennis court access is complimentary, racquet rentals and tennis balls are available at an additional cost.brbrbrbrPlease note that food and beverages are not permitted to be brought onto the Half Moon property, and towel service is not provided for members at the pools or beach. Resort amenity access is limited to a maximum of 10 guests at any one time. On occasion, facilities and guest services may be unavailable due to private hotel events. Half Moon Resort reserves the right to modify or update its membership benefits without prior notice.brbrbrbrThe Neighborhood:brbrLocated in the exclusive Spring Farm area of Montego Bay, Endless Summer offers elevated privacy while remaining close to world-class golf, beaches, dining, and cultural attractions. The vibrant city center and Montego Bay’s well-known shopping and entertainment districts are a short drive away, offering the perfect balance of seclusion and convenience.brbrbrbrGetting Around:brbrWhether you want the freedom of a rental car or prefer to arrive in comfort with a private driver, our team is happy to assist with car rentals and driver arrangements. Airport transfers and personalized transportation can be easily coordinated through our team and our guest app, Privé by CVE, ensuring thoughtful support is always within reach as your plans take shape.brbrbrbrOther Things to Note:brbrEndless Summer includes a dedicated on-site team to support your stay, ensuring comfort, privacy, and a seamless experience throughout. Please note that certain features, amenities, natural conditions, and access to nearby resort amenities and beach facilities may be subject to availability, seasonal changes, and local policies. brbrbrbrGratuity for the villa staff is customary and greatly appreciated. Recommended staff gratuity at the end of your stay is 10% of the villa rental rate during High Season and 15% during Low Season, divided among staff members in accordance with the Gratuity Guide provided in your villa’s Welcome Book. It is standard within the villa industry to observe these guidelines. Gratuities and grocery funds are best prepared in cash, in US dollars. Tips are typically given on the day of departure or may be prepaid at the time of booking. A handwritten thank-you note is a thoughtful personal touch and is always warmly received by the villa team.brbrbrbrBeyond just a stay, Endless Summer offers a refined Caribbean escape where every detail is designed for comfort, beauty, and unforgettable moments.brbrbrbrInteraction with Guests:brbrOur Caribbean Villa Escapes team is available before arrival and throughout your stay to assist with planning, recommendations, and personalized arrangements. While your privacy is always respected, support is always within reach.brbrbrbrRelax and settle in knowing your on-site villa team is available throughout your stay to ensure your comfort. For additional assistance at any point during your stay, our guest app, Privé by CVE, allows you to connect easily with our team, ensuring thoughtful support is always at your fingertips.

7

Bed

7

Bath

16

Sleeps

$72.14

/ Nightly

Private Vacation Home

Charming 2-bedroom bungalow with WiFi and AC in Montego Bay

Montego Bay, Saint James, Jamaica

Stay comfortably in Montego Bay at this 2-bedroom bungalow. The bedrooms feature a pleasant mix of a queen and full bed, ensuring a good night's sleep for all guests. Enjoy the cool breeze on the patio while sipping your morning coffee. With amenities like WiFi, a washing machine, and AC, your stay will be nothing short of brilliant. Our place is equipped for both long or short stays to make your holiday one to remember.

2

Bed

1

Bath

4

Sleeps

$124.0

/ Nightly

Apartment

Beautiful rental-5mins to beaches, restaurant, shops & bar

Montego Bay, Saint James, Jamaica

Stay in this spacious house and live like a true local in Montego Bay, Jamaica . We're within driving distance to restaurants, bars, and beaches. Our rental comes with 3 bedrooms, 2.5 bathroom, kitchen, and living room , Wi-Fi, free parking, friendly workspace -- we've got everything you need. It's within driving distance to several popular restaurants, bars, shops and beaches. An ideal base to explore Montego Bay, Jamaica .

Bed

Bath

Sleeps

$2595.17

/ Nightly

Villa

Dreamtime 7-Beach, Butler, Chef, Driver, Modern

Montego Bay, Saint James, Jamaica

• Dreamtime by the Sea: a contemporary luxury villa with 7 bedrooms and 7.5 bathroomsbr• Location: beachfront in Montego Bay, 12 minutes from the airportbr• Special offer: complimentary 15-seater van and driver for weekly 7 NIGHT bookings, including airport transfers and trips to Negril and Ocho Rios (guests pay for gas and tips)brbrbr 7 bedroom, 7 bathroom modern beachfront villa in Montego Bay -Located on Jamaica's enviable beachfront, Dreamtime by the Sea is a contemporary luxury villa. The Jamaica villa has seven luxurious bedrooms and 7.5 bathrooms. Located in the picturesque Montego Bay area, 12 minutes drive from Montego Bay Airport, this is one of the newest villa rentals in Jamaica. The villa’s architecture is very modern and based on sleek, modern lines.brbrGuests cannot help falling in love with Dreamtime by the Sea from the moment that they enter through the electric gates. The property presents a picture-perfect view with mango, banana, Ackee, and plantain trees. Whichever fruits are in season, guests can enjoy them fresh off the trees. The distinct oriental ambiance of Dreamtime by the Sea makes it very welcoming. A collection of exotic bromeliads and bamboo plants lines the entrance. Guests are offered a warm welcome with the villa’s favorite tropical beverage and cold towel. This Jamaican villa's living room overlooks the turquoise waters of the Caribbean Sea.brbrA magnificent infinity swimming pool is situated directly in front of the living room. The pool deck offers fabulous views of diving boats, fishermen passing by, and the most wonderful sunsets. Very comfortable lounge chairs are available on the pool deck. Beautifully landscaped gardens surround the pool area and the villa. The Jamaica villa’s location offers fabulous views of the sparkling waters of the Caribbean Sea and Montego Bay.brbrThe second living room located on the first floor of Dreamtime by the Sea has large sliding doors that look out to the Caribbean Sea. It has a very elegant décor and is comfortably furnished with large sofas. The games room is another living area with ocean views and several games, including Monopoly, Scrabble, Chess, Cluedo, card games, and many more. There is a wonderful high bar table for playing the 12+ games, while enjoying views of the Caribbean Sea and the swimming pool area! Walk out to an outdoor verandah with comfortable seating and awesome sea views!brbrThe experienced and attentive staff at Dreamtime by the Sea is a delightful, warm, and dedicated professional team comprising a staff of five. They serve guests with traditional Jamaican hospitality. All the staff is sufficiently trained and has the necessary experience to meet the guests’ expectations, and includes a chef, butler, housekeeper, laundress, and gardener/pool man. The chef has his own personal garden with fruits and vegetables that he has planted himself.brbrDreamtime by the Sea has seven bedrooms, each with its own en-suite bathroom. Four bedrooms are upstairs and 3 downstairs. All bedrooms are equipped with air conditioning, ceiling fans, and 40-inch Samsung cable televisions.brbrBedroom ConfigurationbrbrBedroom 1 ~ Ground floor, suitable for the physically challenged, king-size bed, air-conditioning, ceiling fan, cable television, and ocean views with two double sliding doors. Contemporary bathroom with glass picture window to the shower, double basins for his and hers, granite top bench and modern bathroom fixtures, indoor shower and outdoor garden shower, Kohler fixtures for the outdoor garden shower.brbrBedroom 2 ~ Ground floor, king-size bed, air-conditioning, ceiling fan, cable television, two double sliding doors, most awesome morning views of the swimming pool and the Caribbean Sea. En-suite bathroom with an open indoor shower with a large glass picture window looking out into the outdoor shower. It has double basins for his and hers, a granite top bench and modern bathroom fixtures.brbrBedrooms 1 and 2 each have independent and connected doors, for parents who want to stay in close contact with their children.brbrBedroom 3 ~ Ground floor, queen-size bed, air-conditioning, ceiling fan, cable television, and garden views to the front of this villa. En-suite bathroom with bathtub and rain shower combination, safety grab bars in the shower for extra assistance, window to the oceanfront, and privacy blinds.brbrBedroom 4 ~ Upstairs, king-size bed, air-conditioning, ceiling fan, cable television, large floor to ceiling and wall-to-wall windows, awesome views of the Caribbean Sea and swimming pool, open modern spaces, and tastefully decorated. En suite bathroom with large rainfall shower, hand held shower unit, and double his and her vanity basins.brbrBedroom 5 ~ Upstairs, king-size bed, air-conditioning, ceiling fan, cable television, large floor to ceiling windows, and awesome views of the Caribbean Sea and swimming pool. En suite bathroom, shower with large glass picture window, double vanity, his and her basins, granite top bathroom counter tops, ceiling fan and pendant lighting.brbrFor families who like to stay together, Bedroom 4 and Bedroom 5 have connecting doors, for parents who want to stay in close contact with their children. If not, each bedroom has its own private entrance, and the connecting doors can be closed and locked for those wanting their own privacy.brBedroom 6 ~ Upstairs, king-size bed, air-conditioning, ceiling fan, cable television, views of the garden, golf course, Caribbean Sea and mountains, and private balcony. En suite bathroom with rain shower, open concept showering, and his and her double basin.brBedroom 7 – This is a King bedroom with a sliding door to the balcony and ocean views and swimming pool views. There is a separate shower and toilet for guests in bedroom seven, as well as a wardrobe. This bathroom is the smallest of all the bathrooms in the house.brRoom 8 is the gym upstairs and this is air-conditioned.brbrDreamtime by the Sea accommodates 14 guests in 7 large bedrooms. If there are more guests, the large bedrooms can accommodate another 2 persons with additional twin-size beds in two bedrooms for a total of 16 persons. The extra person charge over the standard 14-person limit is an additional $100 per person per night charge for each additional person.brbrDreamtime by the Sea accommodates 14 guests in 7 large bedrooms. If there are more guests, the large bedrooms can accommodate another 2 persons with additional twin-size beds in two bedrooms for a total of 16 persons. The extra person charge over the normal 14 person limit is an additional $100 per person per night charge for each additional person.brbrSwimming pool size: 17 ft x 34 ftbrOther Notes on the Dreamtime Villa:brThere are 40 inch flat screen TV’s in each bedroom.brThere is a large 70 inch flat screen in the media room.brThere is wifi throughout.brThere is Apple TVbrThere is NETFLIXbrThere is a Stereo system that plays IPod music – so you can take your own music and Bluetooth.brOr you can also listen to internet musicbrThere are rock external speakers outside by the pool.brThere are also indoor speakers in the Living room and Media roombrEach bedroom has air conditioningbrEach bedroom has safes = 6 safe boxesbrThere are security cameras around the perimeters of this villabrThe villa has high electronic gatesbrEach bedroom has a back-to-base security system where the security company response team will be on the property in a few minutes if there is any emergency.brbrBEDROOM CONFIGURATION SUMMARY:brBedroom 1 – King bedbrBedroom 2 – King bedbrBedroom 3 – Queen bedbrBedroom 4 – King bed - upstairsbrBedroom 5 – King bed - upstairsbrBedroom 6 – King bed - upstairsbrBedroom 7 – King bed - upstairsbrbrWait! Please contact us before you auto-book! Our calendars are changing hourly and we want to triple-check that the dates are still available and make sure that your chosen villa is suitable for you. We want to share so many things about this villa and the booking process. We have inspected our villas personally so don't be shy to contact us! We would like to tell you all the finer points, the highlights, the distance from the airport, the nearest grocery store, the staff, transportation on the island, what your cook/chef can prepare for you, expectations for tipping the staff, make sure there are no hidden details or hidden costs….. things that may be important for your group! Speak to us! Email us all your questions! We want your vacation to run smoothly!

Bed

Bath

Sleeps

$1574.7

/ Nightly

Villa

Luxury staffed villa, including staff tips, driver, and beach club

Montego Bay, Saint James, Jamaica

Pimento Hill House is a spacious, private home with a stellar history and has complimentary Beach Membership. The villa was originally a Great House and in the early 50s a French Viscount and his glamorous American wife. Jacques and Vera di Sibour, bought it from the Blackwell family. Chris Blackwell lived at the villa as a child with his mother, Blanche Blackwell. Blanche was a friend of Ian Fleming who wrote all the James Bond books. Fleming apparently based some of his heroines in the books on Blanche. Chris Blackwell is the man behind Island Records and credited with bringing the music of Bob Marley to the World. The 50s were a time when Jamaica was a glamorous party destination for the early jet set. Noel Coward and Ian Fleming had houses in Jamaica and attracted a lot of people of note to the island. The Kennedys and many famous actors, artists, musicians and royalty spent the holidays at Round Hill or at house parties in nearby villas. When Queen Elizabeth II and Prince Phillip visited Montego Bay at the end of their Caribbean tour in 1966, they stayed with Jacques at Pimento Hill. There is a scrap book of newspaper cuttings in the villa detailing all the famous guests Pimento Hill has hosted. I am in touch with the Vicomtess's grandchildren and they have been kind enough to send me a lot of personal documents and photographs of the villa. These are also in a scrapbook at the villa.. brbrIn the late 60s Rosser Reeves, a hugely successful American advertising executive and pioneer of television advertising, bought the villa from the Viscount. The AMC program, Mad Men, uses Reeves as the model for the professional accomplishments of the main character, Don Draper (Jon Hamm). Rosser Reeves sold the villa to a German artist who we know very little about and after he sold it back to a local building company in the 80s, the villa fell into disrepair. br brIn 2007 we bought Pimento Hill and extensively renovated the villa while trying to retain the period features. We had holidayed at Round Hill for many years, had fallen in love with Jamaica and wanted to share it with all our family and friends so made Pimento Hill our holiday home. We didn't want to lose the fifties feeling of the original villa so have tried to refurbish it sensitively and with a nod to its very glamourous past. brbrThe villa is surrounded by 6 acres of lush garden with many water features - water lilies, ferns, dragonflies and butterflies abound. There are mango trees, coconut palms, an avocado tree, orchids, night flowering cereus plants and many other tropical flowers in the garden. There are also large grassy lawns to play cricket or football on. There are stunning 180 degree views of the ocean and headland.brbrAccommodation - 9000 sq. ft. Hall, great room, veranda, study, 2 pool bedrooms, 1 bedroom interconnecting with the study, 1 large bedroom in main villa, 1 master bedroom with interconnecting or independent bedroom - all 6 bedrooms have their own bathrooms. brbrThe villa has 7 full-time staff to look after your every need - cook, butler, housekeeper, laundress, 2 gardeners and a night watchman. Also included in the rental is a driver and 14 seat van. br

Bed

Bath

Sleeps

$105.71

/ Nightly

Apartment

Impressive Studio With Captivating Ocean View Overlooking Doctors Cave Beach

Montego Bay, Saint James, Jamaica

ESCAPE THE WINTER in this lovely studio apartment.brbrPlease Note: Even if your desired dates show reserved, please still contact us to check availability.brbrSpectacular ocean/view of Doctors Cave Beach as well as perfect location for watching life along the Hip Strip. Watch cruise ships and flights at a distance from the balcony.brbrApartment Details:br -Studio with King bed, A/C and ceiling fan.br -Cable TV, Free Wifibr -Balcony with Ocean/Beach/Street viewbr -Fully equipped kitchenettebr -Iron & Ironing Boardbr -Linens providedbr -2 beach towels providedbr -Entrance to Doctors Cave Beach $6 per person across the streetbr -Scotiabank ATM directly across the streetbr -24 hr security and Operator, located in Montego Bay ClubbrbrbrArea Information:br -Doctors Cave Beach entry right across the streetbr -Convenience stores within walking distancebr -Craft market about 15 min walk br -Cornwall Beach 5 min walk br -Popular nightlife 5 min walk - Margaritavillebr -Gift Shopsbr -Burger Kingbr br brbrLarger supermarkets a taxi ride away, negotiate the fare before you get in, private taxis located at street level.brbrDistance to major tourist areas:br -5 minutes from Airportbr -5 minutes from downtown Montego Baybr -1 hr from Ocho Rios - world famous Dunn's River Falls and Mystic Mountain for Bobsleddingbr -1 hr from Negril - cliff jumpingbr -20 minutes from Trewlany

Bed

Bath

Sleeps

$120.14

/ Nightly

Apartment

Beryl’s at Seawind on the Bay , Freeport, Montego Bay

Montego Bay, Saint James, Jamaica

located in Freeport , Montego Bay. This air conditioned studio is close to Secrets Hotel , Sunscape Resort (old Seawind hotel) , Yacht club and old Hard Rock Cafe site where we offer free access to Hard Rock's white sand beach. There is a spa next to where the Hard Rock cafe was. Also next door at the Yacht club is the ever popular Seahorse Grill restaurant. The House Boat restaurant is 4 minutes away by car. While it is a short distance (10 minutes )to the Hip Strip , Craft Market and several other Montego Bay attractions. Twelve (12) minutes to the airport. Good transportation is available just outside the gate where there is a taxi stand for both route and chartered taxis. We are close to shops , supermarkets (Progressive supermarket or MegaMart supermarket), fast food outlets , other restaurants and several banks. The studio is situated in a fully gated complex. Freeport is one of the safest areas in the city of Montego Bay. We offer free high speed WiFi and cable TV. There is a safe for your valuables. The tap water is drinkable. Parking is free.

Bed

Bath

Sleeps

$333.33

/ Nightly

Private Vacation Home

Jasmine Palms at Miramar - 3 bedrooms

Montego Bay, Saint James, Jamaica

The Miramar, Spring Garden, Montego Bay is a residential Townhouse Community. brIt is a modern development featuring 24 hours security, an infinity edge pool, gym, playground and ocean views.brbrJasmine Palms, a 3 bedroom / 3 bathroom Townhouse is located at The Miramar Community, Spring Garden, Montego Bay. brIt is only 20 minutes from Montego Bay Airport, 10 minutes from Montego Bay Fairview Shopping Center and 15 minutes to Doctors Cave Beach. brbrThe property is gated with 24 hour security, a resort style infinity edge pool featuring a kids pool, a regular swimming pool and a massage pool. It also has a gym and a playground. brModern finishes grace the interiors, counter tops are granite, solid wood cupboard in kitchen and vanities. Floors are porcelain and marble tiles. brThe ground floor features an open living concept where living and dining areas flow into open plan kitchen. brThe Laundry area is kept separate off the kitchen and the covered garage has direct access to the living area. brOne bedroom, Bedroom #3, furnished with two twin beds is located downstairs with an en-suite bathroom. brThis bathroom also functions as the Powder Room. brbrThe Master Bedroom is located upstairs with a king size bed and very spacious en-suite bathroom, featuring double sinks, bath tub overlooking the water, shower and large walk in closet. The Master Bedroom has its own private balcony overlooking the ocean. br brGuest Bedroom #2 is also located upstairs with an en-suite bathroom and balcony overlooking the pool and the water. brbrIt has an outdoor dining space, a grill and a private lawn space. brbrThe apartment has all necessary appliances and utensils for a comfortable stay and for entertaining.brbrGuests have access to:br - Airport Transfers includedbr - the pool area br - the playgroundbr - Pre-arrival conciergebr - Housekeeping, cooking and baby sitting services on request

Bed

Bath

Sleeps

$2145.0

/ Nightly

Villa

OCEANVIEW LUX 5BR VILLA 180 VIEWS POOL, BEACH/GOLF HALF MOON RESORT MEMBERSHIP

Montego Bay, Saint James, Jamaica

Welcome to our Caribbean villa - TRADE WINDS brbrWe know you will feel right at home with our 5 Star service and will fall in love with Trade Winds and Jamaica. You will have full and exclusive use of our entire villa. brbrThis is your time, and every day is what you make of it. Wake-up to a panoramic view of the Caribbean Sea, drink fresh brewed Blue Mountain coffee and enjoy a breakfast made to order by your personal chef. Plan your day to include a round of golf at one of three outstanding courses – Half Moon, White Witch or Cinnamon Hill – or lounge by the infinity edge pool with your every whim indulged. Opt for accessing the amenities at the Half Moon Resort including sand and surf or a fully equipped gym or stay at the Villa and be pampered with onsite massage treatments. Browse the villa’s unique décor inspired by select pieces from who’s who in the local and Jamaican art scene. End your day in the company of friends and family for alfresco meals or indulge in a romantic dinner for two beneath the stars on the lower deck. Retire to your sea view room as early or late as you choose in the comfort of knowing you get to do it all over again tomorrow.brbrThe Villa is located overlooking Half Moon Golf Course adjacent to 10th hole and set within the exclusive gated community of Spring Farm and yet is only at a 10 minute drive from the Airport.brbrNEW LUXURY VILLA – “Trade Winds”br12,000 sq ft 5 bedroom fully staffed villa overlooking the Caribbean Sea.br5 bedrooms, 5 en-suite luxury bathrooms all equipped with organic bathroom products, bathrobes, air conditioning and ceiling fans.br40 x 15 Heated Infinity pool with 180 degree panoramic views.brConcierge ServicesbrButler, Chef, Housekeepers, Laundress and GardenerbrSecure Gated CommunitybrIncludes one round trip airport transfer from Sangster International Montego Bay AirportbrComplimentary Driver and vehicle for 7 night bookings (gas & tip extra)brComplimentary Luxury Resort Membership to Half Moon Resort brComplimentary Access to 3 outstanding Championship Golf Courses Half Moon (excludes Caddy & Cart) White Witch (open November thru April) and Cinnamon Hill (Guests pay reduced Green & Cart Fee)br Indoor dining and outdoor dining optionsbrTwo Stunning 40ft verandas with breathtaking 180 degree views. brTwo Outdoor TV Areas with 55” flat screen HD TV’s.brAccess to Apple, Netflix and Prime TV.brOutdoor Bar with amazing viewsbrFoosball TablebrOutdoor Gas GrillbrOpen Access to secure WIFi through the entire property including the pool deck.brSONOS Bluetooth music system. brbrBedroom Configuration: All bedrooms are equipped with flat screen TVs and SONOS Bluetooth Speakers, Aqua Tunes, Air Conditioning and Ceiling Fans.brbrMain HousebrbrMaster Bedroom Suite - St Andrew - King Bed with large windows and bi-fold doors with amazing ocean views and direct access to large open veranda with comfortable outdoor wicker furniture. This veranda overlooks both the swimming pool and the ocean with beautiful views. Flat screen TV. Desk and seating area. Luxurious en-suite bathroom with shower, freestanding soaking tub and double vanity sinks.brbrBedroom 2 - St Mary - King Bed, Flat Screen TV. Bright Large Bedroom with bi-fold doors with amazing ocean views and direct access to large open veranda with sumptuous outdoor wicker furniture. Luxurious en-suite bathroom with large walk in shower.brbrBedroom 3 - St Thomas - Garden bedroom - Queen bed with luxurious en-suite bathroom with large walk in shower, Flat Screen TV.brbrAdjacent Poolside CottagebrBedroom 4 - St Catherine - King Bed. Flat screen TV. Luxurious large Indoor/Outdoor Bathroom. Sumptuous Soaking Tub, Indoor Shower, Double Vanity leading to secluded outdoor shower and garden.brbrBedroom 5 - Portland - King Bed. Flat screen TV. Luxurious large Indoor/Outdoor Bathroom. Sumptuous Soaking Tub, Indoor Shower, Double Vanity leading to secluded outdoor shower and garden.brbrPlease note that Bedrooms 4 & 5 can be adjoining rooms as a small shared kitchen connects both bedrooms so ideal for families. Alternatively both bedrooms can be completely private.brbrThe villa comes with a full-time Professional Chef, a personal butler, a gardener and two housekeepers, to take care of your requests allowing you to completely relax and have a perfect vacation.brbrWe can also arrange massages treatments to help you completely unwind. These can be taken at the villa on the covered private spa deck for you to enjoy the Caribbean breeze and views.brbrAlthough we doubt that you will want to leave this private paradise, the villa does come with complimentary membership to the luxury Half Moon Resort. Amenities includebrPristine Crescent-shaped golden sand beach with Beach butlers.br3 Swimming Pools - Eclipse infinity edge pool, Hibiscus Pool with swim up bar & Olympic Lap PoolbrJacuzzisbr9 floodlit Tennis Courts with professional coach br8 Pickle Ball CourtsbrFitness Centre 1,330 sq ft with cardio and weights room. brMiniature Putting Green. Croquet GreenbrKids Club (Additional charge)brHorseback Riding (Additional charge) brWatersports - snorkeling, kayak, paddleboard, sailing, scuba, water skiing, tubing, parasailing, wakeboard, glass bottom boat (Additional Charge for some activities)br7 Restaurants including two gourmet Restaurants, the Sugar Mill (a short walk from the villa), which boasts views of the lush tropical landscape in which sits a historic water wheel of the former Rose Hall Sugar Plantation. Also the award winning Delmare Restaurant overlooking the sea which specializes in fresh fish and seafood with Italian Influences.brbrWe can also assist if you wish to explore further afield with your driver who will act as your personal guide. Perhaps take a day trip to visit our wonderful Island which has so much to offer such as river rafting, fishing, snorkeling, glass bottom boat rides, sunset cruises and private charters plus amazing waterfalls to name a few.

5

Bed

4

Bath

10

Sleeps

$348.0

/ Nightly

Villa

Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.

Montego Bay, Saint James, Jamaica

Hello I'm Mel Thank you for looking at Windfall Villas, I'm sure you will enjoy your stay with us. While deciding on a place to stay, your comfort and safety is first, It also has to be cost friendly….within your budget. With that in mind lets talk about what you get. Free transportation from the airport to A fully equipped, user friendly, 3 bedroom, 4 bathroom villa, located on a very safe and comfortable property, 15 minutes from the airport. Transportation (with seating capacity for 6) available on property. Every bedroom is air conditioned and has its own bathroom. Free wifi, cable, and hot water. There is an out door bar and BBQ grill, 2 out door lounge areas, one with ping pong table (table tennis) and exercise machines, also a house keeper to make sure you don’t work while on vacation, (laundry services available on property). Ask about our food plan options. The pictures will help you visualize the beauty of this property and the reviews will allow you to look through the eyes of experience (those who have been there and done that). Thank you for your time and interest.brbrWindfall villas: An estate available for rental to individuals, couples, small groups (events are allowed at an additional cost) – medium sized families; a haven for relaxation; beautiful, natural, modern yet authentically Caribbean brA place to get away from life’s stressors and back to what’s important to you, family connections. brWindfall Villas is more than just a roof over your head, but a villa you can call your own. Enjoy the spectacular view of the ocean, the hills, and Montego Bay from 2 covered outdoor living areas, and the pool. WindFall villa is a fun, comfortable, safe, colorful, vacation getaway, with a great staff. The housekeeper and airport pickup are included in the rate...brbrIn the morning have your coffee, and get swept away by the ever changing sea and sky while listening to the songs of the tropical birds... Watch the ship come in... A walk on the Beach, a one mile drive away, is an amazing way to start your day, then take a dip in the sea. Maybe get your dinner from one of the local fisherman, or go out fishing with them and catch your own!brbrDuring the day, you can lounge by the pool, play ping pong, stare at the ocean, (we get an amazing breeze off the sea), go snorkelling, take a relaxing bamboo raft ride on The Great River, or you can take a day trip. There are literally hundreds of attractions and adventures in this paradise for a person to have all the fun and excitement one can stand!brbrIn the evening, you will be mesmerized by the harmonic sounds of the tiny tree frogs, while gazing at the twinkling lights of Montego Bay and the hundreds of shimmering stars. You watch the ship leave port, it's like a sparkling little city floating by...brbrCome, lose yourself in this tropical paradise!

3

Bed

4

Bath

5

Sleeps

$600.0

/ Nightly

Villa

Beautiful Tranquil Villa In The Upmarket Area Of Ironshore Montego Bay

Montego Bay, Saint James, Jamaica

Set in the gorgeous and up market area of Iron shore in Montego Bay, this luxurious villa is truly your home away from home.brbrThe Property boasts 9 Ensuite guest Bed rooms with a combination of twin bedroom, Double bed rooms and two master King-sized Suites.brbrDont be concerned about the heat, each room is air-conditioned for your comfort. brbrThe property also boasts distant sea views from the upper floors.brbrThere is a fully-equipped kitchen and laundry room for your convenience.brThere is also a cleaners quarters and a property manager area on site. Staff are here to make your stay the trip of a lifetime.brbrThere is a sunbathing area and a beautiful pool for you to cool down. The property boast a beautiful garden for your relaxation, there are also seasonal fruit trees with local fruits , which you are welcome to pick and eat fresh.brbrSo how far are we from the airport Glad you asked, we are located less than 10 minutes away from the airport.brbrWhat amenities and attractions are close by There are plenty of amenities such as supermarkets, restaurants, bars, Golf courses, all within walking distance from the property.brbrNegril and Ocho Rios are less than an hour by car from the property and are easily accessible by the new highway. brbrHow far is the beach Montego Bay has many beaches. There are beaches less than 5 minutes away by car.brbrHow do I get around There are many options depending on budget. You can walk to many places in about 15 to 20 minutes. You could rent a car from one of the many car rental dealers, or you could call a local taxi operator who will pick you up outside the villa. There is also a shared taxi service service which cost about $1.20 USD to the town centre! Yes that's right, less than two dollars!brbrWhile you are with us we can arrange for you to have your own private chef at an additional cost, who will make you whatever you desire. There is a bar on site which we are happy to open for you.brbrWe can arrange additional services such as massages, hair braiding, etc.brDaily cleaning service and a friendly smile are already included in our prices.brbr

9

Bed

9

Bath

16

Sleeps

$292.0

/ Nightly

Villa

De Ja Vu Villa

Montego Bay, Saint James, Jamaica

Deja Vu villa is a luxurious, three-bedroom villa, located in an exclusive area, Ironshore. This villa is a private booking with a private pool sitting on a half acre land. It is situated on a hillside overlooking the Caribbean Sea.brbrAt your disposal is a house keeper. She has her own quarters and is completely optional. Driver and vehicle are available 24h for charter. The villa is situated 10 minutes drive from all amenities.brOther things to notebrWe would like you to be aware that the housekeeper is completely optional and is included. It is your choice. This is a private booking with a private pool.

Bed

Bath

Sleeps

$1267.0

/ Nightly

Villa

New Listing! Staffed Private Villa/Majestic Ocean View/Pool/10 min Beach/WiFi

Montego Bay, Saint James, Jamaica

brThe property in located in Unity Hall, Montego Bay, and is nestled on 1.4 acres of land. It is situated at the very top of the street @ 1000 feet above sea level with an unencumbered 270 degrees of unquestionably one of the most spectacular views anywhere on earth.brbrFEATURES:-brbr1. Comfortably adorned bedrooms to make you feel like you’re sleeping on heavenly clouds to ensure your stay is as restful as it is relaxing.brbr2. With a majestic ocean view, elegant garden, air conditioning in every room and a meticulously maintained pool, Blue Heaven Villa is sure to please.brbr3. From a relaxing massage, to home cooked poolside meals and everything in between, we have what you need for a relaxing vacation.brbr4. The pretty living room has extraordinarily comfortable overstuffed sofas and chairs and has a 60″ flat screen TV with DVD and ipod / HDMI connection. brbr5. On the main floor, wide glass doors and cedar louvres open to the wrap-around verandah. The perspective is mesmerizing day and night … sunrises and sunsets, cruise ships, tropical lightning shows on the distant horizon, and the twinkling night lights of the town across Montego Bay.brbr6. Adjoining the living room is the colorful den, also with 56″ flat screen television and assorted games… an ideal playroom for children. A daybed in the den can accommodate one extra child. Twin-size air mattresses are available as well. Just outside the den is a removable gate should parents wish to control access of children to the pool area.brbr7. Amazing 16′ x 32′ private pool with a large patio overlooking Montego Bay.brbr8. BEACHbrbrThe beach is well planned for parents and children. Have lunch at the beach bar. Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it). Jog the marked trails. Snorkeling, kayaking, Hobie Cat and sunfish are complimentary. Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees.brbr9. WELLNESS & FITNESSbrbrTryall is blessed with a natural environment that is wholly conducive to a sense of wellbeing. To be surrounded by green in all its spectrum of shades, mature trees, flowering shrubs and the chatter of birdsong instills an aura of calm, peace and tranquility. Along our coastline there are many secret spots to retreat to where you can listen to the waves wash over sand or crackle over white pebbles.brThere are numerous other ways in which your fitness regime can be maintained and enhanced at the Tryall Club.brbr10. GOLF 18 Holes and TENNIS 9 Tennis CourtsbrbrNestled on 2,200 acres, Tryall’s golf course is among the most beautiful in the world. Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events. The resident pro offers workshops and private lessons. The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call. All white attire required.brbr11. THE GREAT HOUSEbrThe 19th century Great House is at the heart of the Tryall Club as well as an important part of the Club’s and Jamaica’s heritage. Built in 1834, it commands a strategic position atop a hill with a beautiful oceanic panorama that extends from west to east.brEnjoy weekly events like complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.brbr12. RELAXING MASSAGESbrNo pre-recorded ocean sounds for this massage. You can enjoy a relaxing massage on the verandah where the sounds of the ocean, and cool breeze will whisk your worries away.brbr13. MASTER BEDROOMbrbrKing Size Bedbrbr2nd FloorbrbrPrivate BathroombrbrKing size bed. Large private bathroom with double sinks, walk-in shower, bidet, Jacuzzi tub. The only room on the second floor. Glorious view!brbr14. BEDROOM 2brbrQueen Size BedbrbrPatio AccessbrbrQueen size bed, door to pool terrace. Shares bathroom with bedroom 3. Bathroom has double sinks and tub-shower combination.brbr15. BEDROOM 3brbrKing Size BedbrbrPatio AccessbrbrKing size bed, door to pool terrace. Shares bathroom with bedroom 2.brbr16. DEDICATED STAFFbrbrOur dedicated team will do everything in their power to ensure your stay is heavenly. From custom meals, to meticulously maintained facilities and grounds, we’re here to ensure your stay is enjoyable.brbrSECURITY:brbrThe community is safe, as most of the homes and Villas including Blue Heaven Villa are regularly patrolled by Hawkeye and Kings Alarm Security Companies. The property has five additional levels of security:-br br1. Remotely activated electronic gates.br br2. Electronic Security whereby all windows and doors are electronically monitored with contacts that feed directly into Hawkeye central monitoring station when the system is armed. br br3. A total of 9 cameras that monitor all points of access on the periphery of the property.br br4. On site supervision as the helpers quarters permit the butler, to sleep overnight whenever there are guests.br br5. Discreet personal security guard 24/7 whenever there are guests.br brOne may choose to rent a car, or one may utilize our extremely reliable driver to do the 10 minute commute to and from Tryall’s Private Beach, Golf and Tennis Resort, as well as excursions for a prescribed fee. The 20 minute airport transfer to and from the property will be covered by the undersigned; one round trip only.br brA reasonable budget for food would be US$60 - US$80 per person per day not including alcohol. The staff will shop, prepare and serve your meals and present you with a grocery bill for settlement.br brIt is expected and customary at the end of your stay for guests to tip the staff. A minimum tip of US$30.00 per room per night should be considered.br brFinally prospective guests are encouraged to visit our website and access the “experiences” subheading, as we are convinced that BHV offers an exceptional value, and a truly memorable stay.br brSincerely,brbrYour Blue Heaven Villa Team

Bed

Bath

Sleeps

$118.8

/ Nightly

Private Vacation Home

Sky View Villas @ Edmund Ridge Estate

Montego Bay, Saint James, Jamaica

Kick back, relax in this calm, luxurious and stylish house, very comfortable and modern style furniture, Views of the mountains and ocean, clean and friendly environment, very quite community with cool windy atmosphere , never a dull moment at this house. In the hills of Rosehall, Community call Edmund Ridge Estate, overlook the Rosehall beach, this property is 5 minutes from free beach, 10 minutes from Sangster International Airport, 5 minutes from shopping mall, 15 minutes from the Hip strip.

2

Bed

1

Bath

5

Sleeps

$133.88

/ Nightly

Private Vacation Home

Cozy Luxury Meadows With Free Wifi, Parking & Hot-tub 2

Montego Bay, Saint James, Jamaica

Gated Community 24hour Security With Amazing View That Comforts You With WiFi,,Tennis Court And Basketball Court . Breathtaking House With Modern Decor From Indoor To Outdoor With All Latest Technology And Amenities.This Property Will Full Fill Your Vacation Whether For Work Or Pleasure.brbrThis Property Is 10minutes From The MBJ Airport And 5minutes Away From All Major Hotels ,Shopping Centre And Clubbing’s .Come Enjoy The Sunset ,Outdoor Hot tub And All Beautiful Things About This House.

Bed

Bath

Sleeps

$119.29

/ Nightly

Private Vacation Home

PENTHOUSE VIEW AND FLATS VACATION HOME (#1)

Montego Bay, Saint James, Saint James, Jamaica

A beautifully built home located in Westgate Walk, Westgate hills Montego Bay St James .its modern style décor, spacious and comfort living will leave you in awe .This apartment provides 2 full furnished bedroom that sleeps up to 4 people , kitchen and dining, 1 full bathroom and a spacious living area with need amenities and your own private balcony.For your needed security and comfort, we provide Wi-Fi ,internet tv, air-condition and remote gate . A home a way from home kids friendly environment.

Bed

Bath

Sleeps

$574.93

/ Nightly

Private Vacation Home

Entire Cozy Luxury Meadows With Free Wifi,Parking&Hottub

Montego Bay, Saint James, Jamaica

Gated Community 24hour Security With Amazing View That Comforts You With WiFi,,Tennis Court And Basketball Court . Breathtaking House With Modern Decor From Indoor To Outdoor With All Latest Technology And Amenities.This Property Will Full Fill Your Vacation Whether For Work Or Pleasure.brbrThis Property Is 10minutes From The MBJ Airport And 5minutes Away From All Major Hotels ,Shopping Centre And Clubbing’s .Come Enjoy The Sunset ,Outdoor Hot tub And All Beautiful Things About This House.

Bed

Bath

Sleeps

$268.5

/ Nightly

Apartment

Bayview Apartment Montego Bay Montego Freeport

Montego Bay, Saint James, Jamaica

Ideally located in the Freeport area of Montego Bay this upper level 2-bedroom apartment is perfectly situated to enjoy a great Jamaican holiday. The apartment shares a large pool and activity area for kids, as well as access to a white sand beach, Seawind Beach Club. brbrApartment has a master bedroom with a king-size bed and a second bedroom with three twin beds; full size living room, dining room and outdoor patio that overlooks the common pool area and gardens.

Bed

Bath

Sleeps

$100.85

/ Nightly

Apartment

2 Bedroom fully air-conditioned 6 mins from Airport

Montego Bay, Saint James, Jamaica

A quiet, cozy modern 2 bedroom gated apartment fully furnished, 6 minutes from the airport 8 minutes from the beach.brUse your voice or smart phone to open/ close the door, turn lights on and off, turn TV on/ off.brAir conditioning in both Bedrooms.brApartment has everything you need to be comfortable whether you stay in or go out this is the place.brTaxi available on demand. Airport pick up & drop off.brTours Available to anywhere. Rates are negotiable and are the cheapest in the island.brbrUse your voice to turn lights on and off, control the door, ceiling fan, check the status of the door, check on the weather at home, and lots more. brThis smart home will make your time indoors feels like you are on the USS Voyager (Star Trek). This is also available on smart phone and tablet.brbrImagine opening the front door using your electronic key given to you once you've made a booking (sent to you via airbnb to your your smart phone)brfurther imagine turning on and off the lights in the apartment using your voice, while cooling yourself off using a voice command or smart phone.brcheck on international news and updates, play trivia and other games using voice commands.brLet us make your stay in Jamaica one never to forget.brbrA 2 bedroom refurbished furnished gated apt, br6 minutes away from the international airport. brAir conditioned room, Internet, cable, hot water, warm neighbors. brKing size and 2 twin beds, Washing Machine, brMaid is available on Request brbrShopping Area, approximately 8 Minutes, brAccess to:br- Casinos br- Restaurants br- Shops br- Transportation br- Clubs & NightlifebrTaxi available on Request.

2

Bed

1

Bath

6

Sleeps

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