Luxury rentals in Saint Ann

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Top-rated luxury vacation rentals in Saint Ann

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Luxe

An expansive outdoor area showcases a modern pool surrounded by lounging chairs and manicured grass. A large buttonwood tree provides shade, while inviting ocean views are visible in the background. The villa's sleek architecture and open spaces contribute to a serene atmosphere.

Villa in Ocho Rios

Buttonwood Reef

This property can be booked for only 6 bedrooms as well (12 guests). Please get in touch with the host for more information. One of the oldest buttonwood trees on Jamaica spreads its leaves over a more recently arrived pool at this waterfront property. This sleek new build is part of the all-villa Hermosa Cove resort—and feels like a resort in itself, with private outdoor living areas stretching along the coast. Walk to 2 resort beaches for a swim, kayak trip, or a romantic dinner in a gazebo on the sand. Listen to the surf and feel the ocean breeze on a furnished deck that hovers just above the water, from a lounger on the pool’s tanning shelf, or from a perch in the covered outdoor living area. When you’re hungry, ask the cook to serve lunch at the pergola-covered dining table; if you’re thirsty, the butler can bring a drink out to the pool. The villa spreads over nearly 7,000 square feet—all of it bright and breezy, thanks to sliding doors and an open-concept layout. There are wall-to-wall ocean views from the great room, which has the living and dining areas, and there’s space for kids to play in a separate TV lounge with a pool table. Professional-grade appliances equip the kitchen to feed a group. Follow paths through the resort’s 12 acres of forest to a yoga pavilion, shared pools that cascade down the hillside, and 2 secluded beaches where you can borrow complimentary snorkel equipment or a kayak. Beyond the resort, waterfall hikes, water parks, and shopping are a short drive away in Ocho Rios. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Sea fan: King size bed, Ensuite bathroom with stand-alone rain shower, Alfresco rain shower & bathtub, Television, Sofa, Safe, Ceiling fan, Private balcony, Outdoor furniture, Ocean view • Bedroom 2 - Anemone: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Ceiling fan, Private balcony, Ocean view • Bedroom 3 - Driftwood: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Sofa, Safe, Ceiling fan, Private balcony, Ocean view • Bedroom 4 - Sea Foam: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Ceiling fan, Private balcony, Outdoor furniture, Ocean view • Bedroom 5 - Sea Egg : King size bed, Ensuite bathroom with stand-alone rain shower, Television, Sofa, Safe, Ceiling fan, Direct access to terrace with putting green, Ocean view • Bedroom 6 - Jellyfish: 2 Double size beds, Ensuite bathroom with stand-alone rain shower, Television, Safe, Ceiling fan, Direct access to terrace with putting green, Ocean view • Bedroom 7 - Coral: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Ceiling fan, Direct access to terrace with putting green, Ocean view • Bedroom 8 - Reef: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Sofa, Safe, Ceiling fan, Private balcony, Ocean view FEATURES & AMENITIES • Chef's Kitchen (Limited Guest usage of Professional Equipment) • Air conditioned Bedrooms and TV/Games Room OUTDOOR FEATURES • Oceanfront • Sand pit • Pergola • Putting green STAFF & SERVICES Included: • Chef • Butler • Housekeeping & Laundresses • Pool/Watersports Attendant • Gardener Extra Cost (advance notice may be required): • Food & beverage at extra cost SHARED ACCESS TO AMENITIES AT HERMOSA COVE RESORT Included: • 2 Beaches • Non motorized-water sports • 3 Pools • 2 Forest trails • Yoga pavilion • Tennis court Extra cost (advance notice may be required): • Restaurants • Spa services

Luxe

An outdoor terrace features a refreshing swimming pool surrounded by sun loungers. Lush greenery and tropical trees provide a natural backdrop, while distant ocean views and a softly lit sky add tranquility to the setting.

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

Luxe

An elegant villa is depicted with a spacious outdoor area, highlighted by a shimmering pool. The structure features a combination of modern and traditional design elements, with large windows and a covered patio overlooking the well-maintained garden. Soft lighting creates a welcoming ambiance as dusk sets in.

Villa in Ocho Rios

5 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

Luxe

The villa's exterior showcases a modern design, with spacious terraces and large glass doors allowing for unobstructed views. A clear pool reflects the evening sky, while comfortable outdoor seating arranged around the pool invites relaxation amidst the surrounding lush greenery.

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

Luxe

A multi-level terrace features sun loungers overlooking vibrant turquoise waters. Steps lead down to a private dock and an infinity pool that blends seamlessly with the ocean, framed by lush greenery and the expansive sky.

Villa in Ocho Rios

5 out of 5 average rating, 12 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

Luxe

The villa's elegant exterior showcases a spacious pool surrounded by lounge chairs. Large sliding doors open to a welcoming living area, while a statue adds artistic flair to the landscape. The two-story structure offers a blend of architectural style and serene outdoor living space.

Villa in Montego Bay

Villa Indigo

Villa Indigo- majestic, panoramic views of the Caribbean Sea and lush valleys. Practically a private resort unto itself, fully staffed with butlers, a chef and sous chef, and housekeepers anticipating your every need. Peloton gym, media room, mahogany bar. Villa and Bamboo Cottage each have five en-suite bedrooms, infinity pool and bar. Terraced estate lush gardens, koi ponds, a hot tub, driftwood playhouse. Membership to world-class Half Moon luxury resort and three championship golf courses.

Luxe

The exterior showcases a modern two-story structure with a spacious balcony. Lounge chairs are positioned around a heated pool, offering a clear view of the water. Natural stone elements frame the pool area, enhancing the tropical ambiance.

Villa in Spring Farm

5 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.

Luxe

Villa in St. James Parish

Abacus Villa

Charming Abacus Villa sits upon a hill overlooking Half Moon Bay offering picturesque ocean and garden views from every angle. Enjoy the lovely breeze that flows through the open concept while you relax and unwind. Abacus is a modern luxury villa designed for comfort with a wonderful team of staff that will delight you with gourmet food and service during your stay. "Abacus is beautiful and we have had an absolutely fabulous stay! The staff is amazing- everyone is so kind and thoughtful."

Luxe

A two-story villa is presented with a sleek exterior, featuring large glass windows. The blue-tiled pool reflects sunlight as it sits alongside a well-maintained lawn. Outdoor seating is arranged on the terrace, offering a spacious area for relaxation.

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.

Luxe

A spacious outdoor area features a glistening pool with a hot tub, surrounded by lounge chairs. Lush greenery frames the property, while large windows illuminate the modern architecture of the home as twilight sets in.

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.