Brand new, fully remodeled luxury Condo (new granite kitchen with dishwasher, 2,5 Bath, washer) with large balcony, overlooking the ocean, in a safe and secure building. Centrally located on Hip Strip, across a road from Doctors Cave Beach, short walk to nightclubs, casino, shopping, restaurants....

Situated on direct waterfront in Montego Bay in upscale Freeport. Unwind in paradise in this remodeled spacious waterfront 2 bedroom/2 bath apartment in a gated resort style complex with 24 hour security, large saline pool, kids wading pool, swing set, lovely tropical grounds and located across...

Luxury and Spacious Condo Apartment available for vacation rental on the Hip Strip, Montego Bay, Jamaica Fully Rehabbed Condo in landmark building set in the side of a cliff with entry from the top and bottom of the building. King-size bed with orthopedic mattress Sofa or additional full size...

Just fully renewed Affordable, Luxury and Spacious Ocean front Condo with balcony overlooking Caribbean Sea King-size bed with orthopedic mattress 50 inch LED Smart TV Wifi Internet and Cable TV Solid bamboo flooring Washer in the condo Fully equipped kitchen with granite counter tops,...

2 Bedroom Apartment, 6 minutes drive from the airport. Everything available for your comfort and relaxation. Use your voice to turn lights on and off, control the door, the television, ceiling fan, Air conditioner, check the status of the door, check on the weather at home, and lots more. This...

Reef House comprises a one story, mid-century Jamaican beach house and guest cottage. The design highlights the natural beauty of the setting and embodies the concept of “outdoor living.” The house has been updated to accommodate modern day necessities while keeping its original character. The main...

Nianna Coral Bay is a fabulous vacation community featuring five 2-bedroom 2-storey townhouses with views of the Caribbean Sea. The beach is a 45 second walk away. The community has an infinity edge swimming pool, is enclosed by a remote controlled gate and secured with a guardhouse. Each townhouse...

One of the finest villas at Tryall Club, Anticipation has all the inviting atmosphere of an elegant private island home and all the amenities necessary to ensure a successful Caribbean vacation. There are three bedrooms in the main villa and one in a separate cottage a breath away from the pool....

This beautiful 2 bedroom cottage sits inside the greater Nianna Estate. With it's own privacy and access the Estate's infinity edge pool and luscious fruit-bearing gardens this is a great getaway for a family or group of 6. The cottage itself is uniquely designed from furniture sourced globally and...

Affordable, Luxury and Spacious Ocean front Condo with balcony overlooking Caribbean Sea King-size bed with orthopedic mattress + sofa bed 2 Full size beds Two 50 inch LED Smart TV Wifi Internet and Cable TV Washer in the condo Fully equipped kitchen, breakfast place, Microwave and Fridge...

Relax in beautiful Rose Hall away from the hustle and bustle of the city. Just a few minutes drive and you are at the beach where you can spend all day swimming, tanning, eating and just relaxing every day. There are lively spots along the coastline where you can enjoy cold beers, cocktails and...

Village Maria Montego Bay, Jamaica: Housekeeper. Free Chef with stay of 5 night or more for breakfast and dinner (you buy groceries) or $60 per person per day all inclusive, breakfast and dinner (no need to buy grocery) Free airport pick-up and drop-off. The community: Nestled in this small...

Come to Celebrity Villa Jamaica where the luxurious accommodations and impeccable service are fit for a STAR celebrity! The beautiful mansion is a NEW CONSTRUCTION 6,000 sq ft 7 BR/ 7 BA plush estate home nestled on an ocean view mountain in the prestigious Iron Shore resort community in Montego...

Quiet studio apartment with own patio on Hip Strip, in a middle of everything in Montego Bay. Nightclubs, beaches, restaurants, shopping, deep sea fishing, catamaran cruses, snorkeling, diving The studio has a fully equipped kitchen, AC and ceiling fan, cable TV, Wi-Fi, towels, linen, a swimming...

Formerly Villa Viviana and now in new ownership, Annabella is built on two levels and surrounded by 6 acres of gardens on an elevated stretch of Mahogany Drive. The world famous Tryall Golf Course, private white sand beach, world class tennis, Restaurants, Kids Club and more of the resort’s...

My place is close to great views. You’ll love my place because of the comfy bed, the coziness, the kitchen, the high ceilings, and the views. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Located in Rose Hall, St. James in a village called...

Sea View Heights Villa Montego Bay, is a lovely private home surrounded by real authentic Jamaican homes, and luscious countryside. The villa is tastefully decorated in colorful recreational fabrics, satellite TV, VCR, Stereo and comfortable furniture inside and out. The spacious bedrooms are...

COZY COVE is an exquisite, brand new, waterfront hideaway located in Montego Bay's most coveted new address: 22 Freeport. This impeccable house benefits from a powdery white sand beach mere steps in front of the breezy, spacious patio, and an infinity-edge swimming pool. The infinity pool is...

PROMOTION! COMPLIMENTARY VAN/DRIVER FOR 7-DAY BOOKING GOOD FROM 3/1 TO 9/30 Sea Island is a fully-staffed luxury villa situated in Jamaica's beautiful Montego Bay. With over seven private acres and sweeping views of the Carribean Sea, this 6,000 square-foot, 6-bedroom (each with en-suite bathrooms)...

Sundance is a stunning 5 bedroom, traditional Palladian style villa completed in 2006, extending to 6,000 square feet and occupying a quiet 2 acre site with views of the Caribbean. Antique brick and Italian tiled terraces, pathways and extensive planted areas create a magnificant setting for this...

S E R E N D I P I T Y: The faculty or phenomenon of finding delightful, pleasant or valuable things not sought for, while having the wisdom to discern it. This is how we, while aimlessly exploring the island of Jamaica on an anniversary retreat, unexpectedly discovered the spectacular view at...

Great Value , Family Friendly Air-conditioned split level Two Bedroom Townhouse in gated community with 24 hour security, five minutes from airport, city centre , Doctors Cave Beach and Hip Strip .Perfect Home away from Home in relaxed quiet area .Comfortably furnished living and dining area ,...

From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club. Additional amenities include: private chef,...

Serendipity Villa is located in the prestigious Spring Farm neighborhood above and overlooking Half Moon Bay resort and the blue Caribbean Sea. The villa has been totally remodeled with style and for comfort in 2008. Serendipity will delight you. The quiet entrance through a flowering vine covered...

A row of tall coconut palms leads up to Vista Del Mar at the top of the Tryall Resort. Aptly names, 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 a 40' x 40' living room...

This studio is located at the Seawind on the Bay property , Montego Bay , the tourist capital of Jamaica. Close to Secrets Hotel , Seascape Resort (formally the Seawind beach hotel) and Hard Rock Cafe where we offer free access to the beach. Hard Rock also offer a pool and a spa Next to the world...

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. The east view captures the sunrise, Montego Bay and the nearby Great River while the west view provides an equally lovely view toward...

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. Additional amenities include: private chef, poolside shower, snorkel gear, golf available, beach club, bathrobes,...

Karma Bay sits on the Tryall plains, along Country Club Drive. The villa is a brief stroll to the Club’s private white sand beach and the legendary Tryall Golf Course. A short golf cart ride will take you up to the Great House, tennis courts, shops, Kid’s Club and gym. Karma Bay’s six bedrooms are...

Reveille By The Sea sits on the edge of the Caribbean Sea with beautiful views of Montego Bay, Round Hill and Tryall’s beach. It is a lovely three bedroom Villa perfect for the romantic get away or for a family with its own pool on the water’s edge. You can walk to the beach, Tryall’s famous golf...

Linger Longer is located directly overlooking the 13th hole of the Tryall Resort's golf course and the ocean beyond. The villa is distinguished by a unique entrance featuring an enclosed courtyard with the private swimming pool. The interiors feature tasteful furnishings and a spacious living room...

PARADISE PLUM VILLA Located in an exclusive Rose Hall Great House and Golf Club Gated community, offering 4 spacious air-conditioned bedrooms with 4 bathrooms en suite, all with king-size four poster mahogany beds with all bedrooms facing north to the Caribbean sea. Paradise Plum is surrounded by...

Discover this light-filled haven of tranquility, nestled in the hills above Half Moon Bay - while easily accessible to bustling Montego Bay, Jamaica. 7,700 square feet on just over 2 landscaped acres in a gated community. Fully staffed by chef, butler, housekeeper, laundress, gardeners and night...

Overlook is one of Tryall's newest additions to their collection of luxury villas in Montego Bay. With spectacular views of the Caribbean Sea and Tryall's famous golf course, Overlook villa lives up to its name with mesmorizing views. There are 5 wonderful bedrooms all with air conditioning for...

The Round House is a superior villa located on Copperwood Ridge. Nestled in a tropical paradise, the home offers views of the lush Jamaican mountains and Caribbean Sea beyond. The home is built on two levels and offers traditionally styled interiors with some local artwork. The home boasts seven...

Brand new fully furnished 2 bedroom townhouse available in gated communty with 24 hour security for weekly monthly rental. Central air, hot water, internet/cable and washing machine with pool on site. 5 minutes from Sangsters airport, entertainment, shopping area and beach. Additional cost...

Beautiful three story apartment home with remote control gates, five (5) minutes from restaurant and supermarket . Home is air conditioned, with washroom, pool, cabana bathroom, big back yard to hang out and entertain and plenty of parking. Home has great view of the mountains overlooking Montego...

Twin Palms is perhaps the most amazing feat of architecture and design achieved in the Caribbean in decades. Fit for a king and remarkable for entertaining, the villa is designed to accommodate families and friends in extraordinary comfort and exquisite style. Unparalleled architecture and design...

This isn't your every day Villa this property is an Estate I call it my private Traven on the Green, because it very private and is located right outside the main city area of Montego Bay and it coved in green plants and palm trees in a area the locals call 'Barnett Estates' a very Exclusive area...

One of just a handful of Tryall villas which has its own private beach (depending upon the tide), Tradewinds On The Sea has the most spectacular sea views. With its charming detached bedroom cottage, great gathering spaces such as the ocean side pool deck and quarter acre lawn, Tradewinds is a...

Newly renovated studio in the safest neighbourhood of Montego Bay. Steps away from the beach (free access to our guests) and few restaraunts. Only 7-10 min drive from famous Hip Strip. Free parking and swimming pool and 24 hour security. Guest access 24 hour security, two pools and barbeque area....

Chelsea Inn is a safe environment with that authentic atmosphere of living as a local! Dedicated in loving memory for my daughter, it is a safe and fun place. Want you to feel the real Jamaica as we are locals and we will show you the beauty of this truly amazing island at local prices! We are NOT...

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. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a...

From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight-bedroom staffed villa at the Tryall Club. * 8 bedroom/10 bathroom deluxe villa at...

Open, light filled studio with large balcony, overlooking the ocean, in a safe and secure building. Centrally located on Hip Strip, across a road from world famous Doctors Cave Beach, nightclubs, casino, shopping, restaurants. Gated community, 24/7 security, pool, parking, tropical garden,...

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 to A...