Holiday rentals in Castleton

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Top-rated holiday rentals in Castleton

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Guest favourite
Flat in Kingston
4.97 out of 5 average rating, 39 reviews

Ultimate 2BR Penthouse Suite with Amazing Views

Experience unmatched elegance and comfort at this stunning 2-bedroom penthouse in Kingston’s prestigious Via at Braemar. With breathtaking panoramic views, this exquisite haven offers the perfect blend of luxury and serenity. Accommodating 4-5 guests, it’s an ideal retreat for couples, families, or groups seeking a lavish escape. Meticulously designed for an unforgettable stay, this one-of-a-kind penthouse invites you to experience Kingston like never before. Book now for a taste of true luxury!

Superhost
An outdoor seating area features dark wicker furniture with bright turquoise cushions, providing a comfortable space for relaxation. The view includes a landscaped yard with palm trees and a swimming pool, outlined by a wooden pergola and surrounded by vibrant greenery.
Home in Portmore
4.86 out of 5 average rating, 207 reviews

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞

This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

Guest favourite
Farm stay in Eleven Mile
4.95 out of 5 average rating, 130 reviews

Rasta family fruit farm hilltop cabin kingston

If you want real roots Jamaica Our place on di hill aint no faker If you like fresh cool breeze And every kinda fruit pon di trees. Butterflies, birds and plants Sweet Reggae to dance Riddims and a whole heap of flavour, Rasta ital behaviour Hilltop views. Outstanding reviews. A community of family and friends. A memory for life it all depends … if you decide to book now! Authentic cabin/outside cool shower/inside toilet/nature everywhere/ double bed/hammock 20mins airport and kingston

Guest favourite
Home in Port Maria
5 out of 5 average rating, 11 reviews

Glen Sea Inn - cozy inn steps away from the beach

Welcome to the Glen Sea Inn! Come enjoy a more peaceful side to the land of wood and water. Our home has been in the family for many years, originally starting out as a law office owned by my grandfather who worked right down the street. He loved the parish of St. Mary and gave his heart to it and to the community. Glen Sea Inn is an homage to him and a way to continue spreading his love for the parish to others! We hope that you have a peaceful stay and make it your home away from home.

Superhost
A charming treehouse is nestled within lush tropical foliage, supported by a sturdy mango tree. Wooden walls frame the structure, while a covered porch adorned with green accents invites relaxation. Stairs lead down, surrounded by vibrant leaves, enhancing the natural setting.
Treehouse in St. Andrew Parish
4.84 out of 5 average rating, 123 reviews

Treehouse at Prince Valley Guesthouse

Stay in this one of a kind Treehouse on our small coffee farm. You have a birdseye view of this beautiful valley high in the Blue mountains of Jamaica from this lovely mango tree. Relax and enjoy warm days and cool nights in this tropical paradise. There are short walks or guided longer hikes in this area including nearby Holywell National Park. Tour a coffee plantation or hangout in the neighborhood and enjoy a cold beverage. Breakfast and dinner are available at an additional cost.

Guest favourite
A spacious lawn area is dappled with sunlight, featuring wooden lounge chairs and shaded spots beneath leafy trees. The grassy expanse is bordered by a low wall, creating a relaxing atmosphere perfect for lounging or socializing.
Apartment in Golden Spring
4.88 out of 5 average rating, 64 reviews

Kingston Reggae Garden APT river & swimming hole

Kingston Reggae Garden is a chill spot by the river and more than just a guesthouse. Lots of lawn space with speakers playing Reggae music all-day On-site bar and restaurant where you can meet tourists and locals Outside furniture, hammocks and private spots River with swimming hole Party place with great weekend vibes Transportation service and advice on Kingston cultural spaces and events We help you plan trips and activities Remember: we are not a quite place we are a vibes place!

Superhost
A wooden interior features warm tones, highlighted by a spacious bed adorned with nature-inspired decor. Two closed wooden doors are positioned adjacent to a potted plant, with soft lighting provided by a bedside lamp on a small stool. Large windows allow natural light to illuminate the room.
Tiny home in Portland Parish
4.8 out of 5 average rating, 122 reviews

Our Escape, Tiny Home in Blue Mountains w/ River

Get cozy and unplug in nature at this off-grid, tiny home at Our Escape's unspoiled twenty acres property. This rustic cabin offers all modern comforts and is nestled in the Portland side of the Blue Mountains. This unique space serves as the perfect retreat from all the modern world noises. Let the countless bird species serenade you, while you hike or swim in our private river. Let the fireflies be the only lights you see at night while you stare at the constellations.

Top guest favourite
The exterior of the home showcases elegant wrought iron gates framed by white columns. A stone pathway leads through a grassy area, accompanied by potted plants, creating a welcoming entrance that blends architecture with nature.
Home in Richmond
4.91 out of 5 average rating, 11 reviews

Secluded Haven 2 bedroom st Mary Jamaica.

Discover Your Authentic Jamaican Getaway! Welcome to your ideal Jamaican retreat—a charming 2-bedroom escape perfect for both relaxation and adventure. Unwind in comfort with a luxurious king-sized bed and enjoy air-conditioning along with access to Netflix and YouTube. As the sun sets, the property’s warm glow is perfect for BBQs, drinks, and savoring the tropical ambiance. With two convenient entrances and a spacious layout, this home is designed for a memorable stay.

Guest favourite
A serene view is presented of a single-story house nestled among lush greenery, under a dramatic sky painted with hues of orange and gray. The ocean can be seen in the distance, with the horizon blending into the vibrant clouds.
Cottage in Buff Bay
4.9 out of 5 average rating, 20 reviews

Rural trek worth the view farm cottage in Portland

Relax at this unique and tranquil getaway 20 mins drive from the main road (4WD recommended) Nature lovers paradise with exotic fruit farm on property. Amenities including AC, hot water and wifi. Nearby coffee or blue mountain tours, Sommerset falls, numerous beaches and rivers. Guest should expect to see animals, flora and fauna typical of the Jamaican countryside and noises consistent with being on a working farm property

Top guest favourite
A modern bedroom features a spacious bed dressed in crisp white linens and yellow accents. A decorative mirror and framed artwork adorn the walls. A cozy seating area includes a light-colored bench and a gray chair, while a ceiling fan contributes to the airy atmosphere.
Flat in Bog Walk
5 out of 5 average rating, 7 reviews

Church Road Haven

Relax in this modern 1-bedroom, 1-bathroom apartment, just 3 minutes from Linstead and Bog Walk. Offering privacy, comfort, and all amenities, it’s perfect for solo travelers or couples. Enjoy a stylish, cozy retreat in a central yet peaceful location. Whether for business or leisure, this space provides the ideal blend of convenience and relaxation. Book now and make it your home away from home!

Guest favourite
A spacious sleeping area features a large bed draped in a light-colored coverlet. Floor-to-ceiling windows showcase lush greenery and the distant landscape, complemented by wooden furniture including a table and chairs for enjoying the view.
Guest suite in Port Antonio
4.96 out of 5 average rating, 187 reviews

Starfish Cottage

Experience tranquility and beauty at our cottage, perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Delight in the frequent visits from hummingbirds to our feeders, adding a touch of nature’s charm to your stay. Conveniently located, you'll find yourself at the heart of all the attractions that the area has to offer.

Top guest favourite
A cozy studio apartment is shown, featuring a spacious bed, a comfortable sofa, and a wall-mounted television. A wooden door is visible, along with light curtains that frame a window. A small table and fan add to the functionality of the living space.
Flat in Meadowbrook
4.93 out of 5 average rating, 99 reviews

Hidden Border 1 Cozy studio, ac , hotwater, wifi

Outside the hustle and bustle of central Kingston metropolitan area lies this quaint spacious cozy studio apartment in a traditional residential community in Kingston. Lots of fruit trees to bring back memories of old Jamaica with views of the green hills of Red Hills. Just the right distance from all amenities such as, Devon house, The National stadium and halfway tree.

Popular amenities for Castleton holiday rentals

  1. Airbnb
  2. Jamaica
  3. Saint Mary
  4. Castleton