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Villa vacation rentals in Jamaica

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Top-rated villa rentals in Jamaica

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favourite
The Windsor Mansion is positioned at the top of a hillside, surrounded by a lush landscape of trees in various shades of green and hints of autumn colors. The elegant white of the mansion’s exterior contrasts with the natural setting, creating a striking visual.
Private room in Windsor
4.9 out of 5 average rating, 40 reviews

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

Guest favourite
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.91 out of 5 average rating, 23 reviews

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

Top guest favourite
An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.
Villa in Pownal
4.94 out of 5 average rating, 89 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

Guest favourite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 46 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

This unique house has a style all its own. with floor to ceiling windows and doors throughout There are 3 levels. top floor has 2 bedrooms with full baths and Hot Tub on the balcony middle level entry; plus Great room: with kitchen, dining, living, activity area with a big table, fireplace and 75 inch television bottom level has 2 bedrooms and 2 full baths

A game room is highlighted by a foosball table and several pool tables. Green pendant lights hang above the pool tables, providing illumination. The floor features wood-like flooring, enhancing the spacious feel of the area. Walls are painted in neutral tones, contributing to a relaxed atmosphere.
Villa in Brownsville
4.79 out of 5 average rating, 72 reviews

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Superhost
Villa in Killington
4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

Whiffletree C2 has been totally renovated and looks great. Located at the base of Killington close to mountain biking and snow sports.

Superhost
The exterior view showcases an inviting multi-unit building with a unique architectural design. Angled roofs and large windows create an airy feel, while well-kept landscaping and gravel pathways enhance the property’s natural setting.
Villa in Killington

Whiffletree base of Killington outdoor pool

Whiffletree I2 Take the shuttle to the mountain and ski home at the end of the day.

Superhost
A living area features a large sectional sofa facing a stone fireplace with a wooden mount displaying the Killington logo. A television is positioned above a console, while a large window offers views of the outdoors. Natural light brightens the room.
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Whiffletree base of Killington outdoor pool

Whiffletree F6 is on the shuttle bus route with a ski back trail

Superhost
A comfortable living area features a gray sectional sofa and a pull-out sofa bed, positioned beside a circular coffee table. Large windows with sheer curtains allow natural light into the space, while a wooden ceiling adds warmth. A small fireplace and bear-themed wall art enhance the ambiance.
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Base of Killington with Sports center access

Trail Creek 12, Lovely 1 bedroom close to Mountain

Superhost
A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.64 out of 5 average rating, 11 reviews

Base of Killington with Sports center access

Trail Creek 70, Fantastic 3 bed close to Mountain

Superhost
A comfortable living area is featured, showcasing a soft beige couch and a light gray armchair positioned around a wooden coffee table. Natural light filters through large windows, highlighting the wooden ceiling and creating a cozy ambiance.
Villa in Killington
4.6 out of 5 average rating, 5 reviews

Base of Killington with Sports center access

Trail Creek, Lovely 2 bedroom close to Mountain

Superhost
A spacious living area features a colorful floral sofa alongside two brown leather chairs. A wooden coffee table sits in front of the seating. A wood-burning fireplace is located against a textured wall, with vintage skis displayed above it. Large windows allow natural light to enter.
Villa in Killington

Trail Creek 11 is on a ski home trail

Trail Creek 11 is on a ski home trail

Popular amenities for Jamaica villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Superhost
A spacious living area features a colorful floral sofa alongside two brown leather chairs. A wooden coffee table sits in front of the seating. A wood-burning fireplace is located against a textured wall, with vintage skis displayed above it. Large windows allow natural light to enter.
Villa in Killington

Trail Creek 11 is on a ski home trail

Superhost
A cozy living area is enhanced by a large brick fireplace. Two plaid sofas face each other, complemented by a wooden coffee table in the center. A large window allows natural light to fill the space, framed by blue curtains and adorned with seasonal decor.
Villa in Killington
5 out of 5 average rating, 3 reviews

Sunrise East Glade C8 Ski on Ski off

Superhost
A comfortable living area is furnished with a spacious sofa and a wooden coffee table. Natural light floods the room through large windows, providing views of the outdoors. Artwork is displayed on the walls, while a lamp adds subtle illumination beside the seating.
Villa in Killington
4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7 Ski on Ski off

Superhost
Villa in Killington
4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

Superhost
A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.64 out of 5 average rating, 11 reviews

Base of Killington with Sports center access

Guest favourite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 46 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Top guest favourite
An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.
Villa in Pownal
4.94 out of 5 average rating, 89 reviews

Vermont Vacation Villa—Grapevine Getaway

Superhost
Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

Luxury villa rentals

Superhost
Villa in Killington
4.56 out of 5 average rating, 9 reviews

Whiffletree base of Killington outdoor pool

Guest favourite
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.91 out of 5 average rating, 23 reviews

Stonehouse at Stratton

Guest favourite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 46 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Top guest favourite
An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.
Villa in Pownal
4.94 out of 5 average rating, 89 reviews

Vermont Vacation Villa—Grapevine Getaway

Villa rentals with a pool

Superhost
A cozy living area is accented by wooden paneling and a gas fireplace. Two comfortable chairs are positioned with cushions, while a sofa and a wooden side table complement the seating arrangement. Natural light enters through sliding glass doors, revealing a view of the outdoors.
Villa in Killington
2.67 out of 5 average rating, 3 reviews

Whiffletree base of Killington outdoor pool

An indoor pool area is featured, with a spacious swimming pool lined by blue lounge chairs. Large windows allow natural light to fill the room, enhancing the bright atmosphere. The covered structure showcases a high ceiling, ensuring a comfortable swimming experience year-round.
Villa in Brownsville
4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

An indoor pool area is highlighted by clear blue water under a high, metallic ceiling. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Large windows provide natural light, creating a bright atmosphere throughout the space.
Villa in Brownsville
4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

An indoor pool area features a long, rectangular swimming pool surrounded by multiple lounge chairs. The high, vaulted ceiling is supported by metal beams, and large windows provide natural light to the space, creating a bright and inviting atmosphere.
Villa in Brownsville
4.8 out of 5 average rating, 10 reviews

Villa Near Biking and Hiking Trails

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