Luxury rentals in St. Ann Parish

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Top-rated vacation rentals in St. Ann Parish

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Villa in Montego Bay

4.61 out of 5 average rating, 31 reviews

Caribbean Jewel

Nestled in a secluded coastal neighborhood of Jamaica’s gorgeous Montego Bay, Caribbean Jewel is a villa that easily lives up to its name. With four ocean-view en-suite bedrooms, a full staff, and several amazing golf courses and beaches within a few kilometers, your Jamaican vacation will be relaxing, rejuvenating, and unforgettable. All of the traditional elements of luxurious Caribbean architecture are covered and updated, on this modern villa. Details like the low profile terracotta roof, exposed-beam vaulted ceilings, warm wood trim, and wide openings to the terrace are classic examples of Caribbean design. Open those doors, and this villa instantly fills with a fresh ocean breeze and natural sunlight, creating a relaxing, tropical atmosphere throughout. The living room is decorated with plush furniture, state of the art electronics, and plenty of local plants to add a splash of color and freshness. And the kitchen, which switches to a clean white color scheme, is outfitted with high-end appliances and dark granite countertops. Caribbean Jewel’s staff included overnight security, a butler, private chef, laundress, and a housekeeper. There’s formal dining inside and an alfresco set on the terrace, both with seating for twelve. The villa is located within a gated community, and it includes parking. Inside, Caribbean Jewel is equipped with Wi-Fi, cable television, air conditioning, an office space, and a sound system. And, on the terrace, you’ll love the ocean views, the swimming pool, and the spacious backyard garden. Just thirteen kilometers away, Montego Bay’s downtown area is rich with boutique and retail shopping, restaurants, beachfront bars, nightlife, and adventure tourism. Montego Bay’s surrounding area is well adorned with beautiful public and private beach clubs, which you’ll receive complimentary access to Rose Hall and Doctor Cave beach clubs. It’s also a golfer’s paradise. With Half Moon, Cinnamon Hill, and White Witch golf courses all within five kilometers of Caribbean Jewel. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Upper Level • Bedroom 1- Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual vanity, Dressing area, Walk-in closet, Television, Air conditioning, Private veranda, Ocean view Main Level • Bedroom 2: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Television, Air conditioning, Shared balcony, Ocean view • Bedroom 3: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Access to terrace, Ocean view • Bedroom 4: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Air conditioning, Access to terrace, Ocean view Additional Bedding • Den: Sofa bed, Air conditioning, Shared access to powder room FEATURES & AMENITIES • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Babysitting service • More under “Add-on services” below

Villa in Montego Bay

4.5 out of 5 average rating, 4 reviews

Serendipity

Otherwise known as “the occurrence of events by chance in a beneficial way,” Serendipity villa happens to be one of those places that guests are just so happy to stumble upon. The villa provides a casually elegant atmosphere minutes from the airport. Situated on the “Elegant Corridor” in Montego Bay, Serendipity has been modeled to relax the senses and soothe the spirit. The villa features a refreshing swimming pool, water toys and private tennis court. The villa is family friendly and includes a home entertainment system with iPod dock, a music and movie library, Wi-Fi access and baby gear. The villa is also partially wheelchair accessible. A gated property, Serendipity villa provides a full staff, including security. Provide the groceries and enjoy the tasty dishes freshly prepared by your chef, formal dining or casual alfresco - it is all up to you. The spacious and comfortable living areas provide lovely views of the tropical tree tops and turquoise sea from almost every angle. Archways connect the open living spaces and dining areas, thus maintaining a cooling draft and a clear ocean view throughout. Many of the spaces lead to covered terraces where you can enjoy a postcard perfect sunrise. Six stately and breezy bedrooms with ocean vistas accommodate up to twelve guests at Serendipity. Each bedroom includes en-suite bathroom, air conditioning, ceiling fan and TV. The decor in each themed bedroom has been chosen to reflect the clean, modern atmosphere of the villa. Serendipity boasts spectacular 180 degree views that showcase the pristine Half Moon Golf Course and glimmering Caribbean Sea. The villa is also close to a number of other top quality golf courses including the Hyatt Ziva/Zilara and the famed Tryall Club. Or a day trip to the nearby outdoor museum Columbus Park provides clues into an era of exploration through the Spanish colonial artifacts on display. However you spend your getaway, Serendipity happily welcomes you to days of luxury in the warm Jamaican sun. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Safe, Television • Bedroom 2: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 3: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 4: King size bed, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 5: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 6: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan,Television FEATURES & AMENITIES • More under “What this place offers” below Included: • Gardener • More under “What this place offers” below Extra Cost – advance notice may be required: • Activities and excursions • Babysitting service • More under “Add-on services” below

Villa in Runaway Bay

Selah Villa

Please note that this home is in close proximity to an ongoing construction project. Please enquire for more information. Located on the Northern coast of Jamaica, on a private sandy cove just off Runaway Bay Beach, Villa Selah is everything you could hope for in a beach vacation home. Nearby, you’ll find golf, shopping, restaurants, and nightlife, but from Selah’s secluded cove, you’d never know. With four en-suite ocean-view bedrooms, beachfront, a tennis court, watersport equipment, and a full staff, Selah is essentially your own private resort. This multi-level beachfront home features several lounge areas, both inside and out, that capture amazing ocean views. There are covered, and un-covered portions of the terrace and the interior has numerous openings to the outside, ensuring fresh ocean breeze and natural sunlight fill the luxurious interior. Inside, Selah is adorned with beautiful wood furniture and trim, giving it a warm, inviting atmosphere. And, just beyond the living room doors, you’ll love the tiki bar under the covered terrace, it’s the perfect spot for post-dinner cocktails. Selah’s staff consists of a butler, housekeeper, laundress, and a personal chef. Outside, you’ll have access Selah’s sailboat, paddle boards, kayaks, and snorkeling equipment. There’s also a swimming pool and hot tub on the beachfront terrace. Back inside, features like Wi-Fi, television, and air conditioning will make you feel at home. And, at dinner, there’s a formal dining space with seating for eight and an alfresco set on the terrace. The nearest city to Selah is Ocho Rios. Once a small fishing village, it’s now a tourism hub with high-end shopping, fine dining, and a vibrant beach bar atmosphere along its coast. Further inland, you’ll find Dunn River Falls, a terraced waterfall surrounded by pristine lagoons and tropical vegetation. And, of course, there are gorgeous beaches just about everywhere along the coast. One, of many, worth checking out is James Bond Beach, used in the film “Dr. No,” it features truly breathtaking scenery, white sand, and crystal clear waters. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1- Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Ceiling fan, Safe, Balcony, Ocean view • Bedroom 2: 2 Twin size beds, Ensuite bathroom with shower/bathtub combo, Air conditioning, Ceiling fan, Balcony, Ocean view • Bedroom 3: King size bed, Ensuite bathroom with shower/bathtub combo, Air conditioning, Ceiling fan, Safe, Balcony, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Ceiling fan, Safe, Ocean view FEATURES & AMENITIES Included: • Laundress • Gardener • More under “What this place offers” below Extra cost (advance notice may be required): • Cost of food • Laundry service • Activities & excursions • More under “Add-on services” below

Villa in Spring Farm

4.5 out of 5 average rating, 12 reviews

Nianna Eden

Take a morning stroll through the Spring Farms Estate’s 2-acres of private tropical gardens, set just outside Montego Bay in an upscale seaside community. Think about how to spend your afternoon. Is it a trip to the beach? A round of golf? You could do both; they’re only a few minutes away. Don’t decide yet. Head back to Nianna Eden and enjoy your morning coffee while you gaze upon the sparkling Caribbean Sea, it will come to you. Jamaica’s natural features make it an incredible vacation destination. That’s why Nianna Eden invites the fresh sea breeze, warm natural sunlight, and epic ocean views inside to inspire. Merging modern architecture with those features is Nianna Eden’s specialty, as you’ll find intricate stonework, exposed-wood, and carefully integrated tech gadgets. And, the vibrant colors and textures of Jamaican works of art placed throughout the villa are sure to spark conversation on nights in. Grab a book and explore the gardens, play bartender and whip up some fancy new cocktails, or stretch out in a sun lounger and see where the day takes you. On special occasions, get dressed up and enjoy the air conditioning in the formal dining room or commit to the bathing suit, hopping in and out of the pool as you sample freshly grilled treats from the barbeque. And, don’t worry about upkeep, the villa’s staff has got you covered. 6 minutes from home, the prestigious Rose Hall Beach Club, a private club, is easily one of the country’s best beaches. Decorated with coconut trees and pristine white sand, this exclusive beach is a picture of perfection. Wave breaking rocks ensure calm waters, ideal for kids and first-time snorkelers. While the kids play, relax at the poolside grill. After, head 15 minutes West for an exciting night in Montego Bay. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Safe, Lounge area, Air conditioning, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Air conditioning, Garden view • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Television, Safe, Lounge area, Air conditioning, Direct access to pool, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Lounge area, Air conditioning, Direct access to pool, Ocean view • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Safe, Lounge area, Air conditioning, Garden view Features & Amenities • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Villa in Ocho Rios

5.0 out of 5 average rating, 11 reviews

Four Winds

Experience the five-star side of Jamaica at Four Winds. This spectacular Ocho Rios vacation rental has its own private beach, an attentive full staff and amenities worthy of a boutique resort. Make its five bedrooms your temporary home for a family reunion, special occasion celebration or even an oceanfront Caribbean destination wedding—and the honeymoon after. Your holiday at Four Winds includes the services of a cook, housekeeper, butler and nighttime security staff. The villa opens to outdoor areas with a pool, hot tub, tennis and bocce courts, and a glorious white-sand private beach that you can explore with the provided kayak and snorkeling equipment. Other amenities range from a satellite television and surround-sound system to Wi-Fi. Step from the shaded veranda into spacious, inviting living areas with huge windows facing the water, airy ceilings and a laid-back mix of casual and traditional furniture—think wicker armchairs, floral-print sofas and ladder-back seating around the formal dining table. With multiple seating areas at your disposal, there’s plenty of space to gather together or steal a quiet moment with a book. The villa’s location in the popular resort area of Ocho Rios puts you less than a 10-minute drive from shopping and dining, and close to activities from waterfall hikes to zip-line adventures. Follow a stream through the forest to a hidden pool, or make the drive along the coast to the picturesque James Bond Beach. When it’s time to leave, plan on a 90-minute drive to Sangster International Airport (MBJ) Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 – Primary 1: King bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 2: Queen bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe, Direct access to pool • Bedroom 3: 2 Twin beds, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 4: 2 Twin beds, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe • Bedroom 5 – Primary 2: King bed, En-suite bathroom, Air conditioning, Ceiling fan, Television, Safe, Covered porch, Direct access to pool STAFF & SERVICES Included: • Gardener Extra Cost (advance notice required): • Additional guests • Petrol consumption • Babysitting • Day boat rental • Laundry • Tennis instruction • Water sports instruction

Villa in Ocho Rios

Rio Chico

Please note that this listing requires a security deposit. Please get in touch with our Trip Designers for more info. Lily ponds, dangling ivy, and blooming hibiscus set the scene at this Jamaican retreat. A lush, tropical vibe greets you as you enter through wrought-iron gates. With 14 acres at the base of Dunn's River Falls to explore, you’ll discover four enticing pools — one of which leads directly into the turquoise sea. Why not toast marshmallows with a beachside bonfire or sink into the freshwater hot tub? Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Manor House: • Bedroom 1 - Master: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television Balcony, Sea View • Bedroom 2: 2 Queen size beds, Ensuite bathroom with stand-alone shower, Terrace, Sea view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Terrace • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Balcony, Sea View • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Balcony, Sea View • Bedroom 6: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television, Balcony, Sea View Cliff-side Villa: • Bedroom 7: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Terrace, Sea View • Bedroom 8: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Terrace, Sea View • Bedroom 9: 2 Queen size beds, Ensuite bathroom with stand-alone shower and bathtub, Terrace, Sea View • Bedroom 10: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Television Cliff-side Cottage: • Bedroom 11: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Terrace • Bedroom 12: King size bed, Ensuite bathroom with stand-alone shower and bathtub, Terrace FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Babysitting service • Laundry service • Activities & excursions • Housekeeping • More under “Add-on services” below

Villa in Ocho Rios

5.0 out of 5 average rating, 11 reviews

Rocksteady Villa

Spend magical nights stargazing by the dockside fire pit, seaside grotto, or infinity pool at this romantic hideaway in Ocho Rios, Jamaica. Inside, the panoramic sea views continue through the upper levels. Spend your days playing golf, scuba diving, or kayaking around the nearby fish sanctuary. Later, settle in for an incredible alfresco dinner at sunset. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Shared balcony with bedroom 2, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Shared balcony with bedroom 1, Ocean view • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Private balcony, Ocean view, Access to downstairs sitting area • Bedroom 4: 2 twin size beds, Ensuite bathroom with hallway access, Stand-alone shower OUTDOOR FEATURES • Outdoor living area • Private dock • Private water cave and sea cove (accessible at certain times of the year) • More under “What this place offers” below STAFF & SERVICES Included: • Groundskeeper Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Villa in Rose Hall

BougainVilla

Nestled amongst lush greenery and mature trees, this breezy villa enjoys a scenic perch just off the coast of Montego Bay. Swing open the terrace and bedroom doors to fill the interior with fresh ocean air. Step outside to relax by the pool and enjoy the ocean view. When sunset approaches, head to the terrace bar for a tropical cocktail or pick a beach bar along the sandy coast. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Television, Terrace, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Ocean view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Television, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television, Ocean view • Bedroom 5: Queen size bed, Shared access to hallway bathroom, Stand-alone shower, Television • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower, Television STAFF & SERVICES Included • Daily Chef services (breakfast, lunch and dinner; groceries not included) • 2 Gardeners Extra Cost (advance notice may be required): • Activities and excursions

Villa in Spring Farm

5.0 out of 5 average rating, 5 reviews

Villa Rosa

Modern tropical treehouse near Half Moon Beach Open the wooden gates to a palm-lined allée leading to tropical modernism above the sea. A terrace and balconies lined with loungers all face the heated pool with a diving board, and the fitness room opens to a treetop deck for yoga. Settle in for a massage while the chef and butler work the scene, and feel the ocean breeze on a chevron-patterned armchair by the TV. Half Moon is a 2-minute drive. Copyright © Luxury Retreats. All rights reserved.

Home in Tower Isle

Panoramic Cliffside Luxe Villa

Perched on a lush hilltop, the vibrant Caribbean Sea sprawls just beyond this impressive 6 bedroom villa. The sleek interior is drenched in natural light. A blue-tiled pool entices you in for a refreshing dip. Cocktails can be served on the sprawling terrace as the sun sinks below the horizon. Mere minutes from Ocho Rios, discover lively bars and restaurants as well as popular beaches and lagoons. Copyright © Luxury Retreats. All rights reserved.

Place to stay in Runaway Bay

Breakaway

Wavelets kiss white sand on the grounds of this lush Jamaica home. The acre of land is ringed by private beach perfect for swimming or kayaking, and there’s also a pool and hot tub. Plants fill an atrium and living areas like a rainforest, and details like slipcovered chairs and live-edge tables add to the relaxed feel. It’s a short drive to other beaches and caves in Runaway Bay. Copyright © Luxury Retreats. All rights reserved.