Holiday rentals in Wakefield

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Top-rated holiday rentals in Wakefield

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Top guest favourite
A serene pool area is visible, featuring lounge chairs arranged beside a clear blue pool. Palm trees and lush greenery frame the space, while a covered gazebo is provided in the background, enhancing the outdoor relaxation experience.
Townhouse in Montego Bay
4.98 out of 5 average rating, 205 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

Top guest favourite
A charming outdoor area showcases comfortable seating amid lush greenery. The inviting beach and turquoise sea are visible in the background, while a lantern adds a touch of character to the villa's exterior. The space is designed for relaxation and enjoying ocean views.
Villa
4.94 out of 5 average rating, 117 reviews

Ocean Dreams Villa

Ocean Dreams Villa is a stylish, unique, beach villa with 3 bedrooms and 3 bathrooms and sets the stage for a memorable trip within steps of the beautiful Duncans Bay Beach (also known as Silver Sands Public Beach) with its sparkling turquoise waters and white silvery sand, the view is simply breathtaking. It's the perfect ambiance to relax in comfort, enjoy the breeze, listen to the birds, nature and let the soothing sound of the ocean waves breaking on the shore calm you and ease your mind.

Guest favourite
A tranquil swimming pool offers crystal-clear water, framed by lush tropical plants. The serene ocean view stretches beyond, showcasing gentle waves and distant hills under a partly cloudy sky. Lounge chairs are positioned nearby, inviting relaxation by the water's edge.
Home in Montego Bay
4.92 out of 5 average rating, 65 reviews

"Smallah" 4-br seaside villa own pool, resort area

Welcome to Smallah Villa, our spacious and elegantly designed 4-bedroom, 4.5-bathroom oceanfront townhouse in the Freeport Area of Montego Bay! This stunning property is the perfect getaway for families or groups of friends looking for a relaxing retreat in Caribbean Paradise. It comfortably accommodates up to 10 guests. With private infinity pool and a pier for private boat pickup. Premium Services ($ - Additional Fee) • Grocery Shopping & Delivery Service ($) • Cook & Clean ($) • Driver ($)

Guest favourite
The exterior of the home features a welcoming entrance with a small, shaded porch area. Large windows provide natural light, while carefully arranged plantings create a serene environment. The architectural design combines neutral tones with a distinct gabled roof.
Home in Falmouth
4.88 out of 5 average rating, 48 reviews

Urban Loft

This newly renovated, fully furnished, one-bedroom apartment offers a serene and sophisticated ambiance in a beautifully decorated semi-attached unit. Amenities include a/c unit, water heater, and an indoor laundry room. The property features a spacious backyard within the secure, gated community of Holland Estates, providing a peaceful outdoor retreat and 24-hour security. Its convenient location offers 5 to 10 minute access to the Martha Brae River, Luminous Lagoon, and Falmouth Pier.

Guest favourite
A modern living area is shown featuring a large, comfortable sectional sofa with decorative pillows. A round coffee table sits in the center, topped with an item. A flat-screen TV is mounted on the wall, and natural light filters through sheer curtains over a door.
Flat in Rose Hall
4.78 out of 5 average rating, 36 reviews

Berry on the Hill~2

Whether pleasure or business, this Chic, modern rental home with ocean views, within the Montego Bay area; 15 mins from the MBJ Airport and 3 mins from "The Elegant Corridor," is all you need. Serene, centrally located; near major golf courses, hotels, shopping malls, beaches and attractions such the White Witch of Rose Hall, rafting on the Martha Brae River and the Montego Bay Conventional Center. Personalize your trip with a chef and tour guide. Berry on the Hill awaits you...

Superhost
A spacious living area features a large blue sectional sofa with decorative pillows. Bright light filters through sheer curtains, illuminating the glossy floor. A modern ceiling fan hangs above, and a dining space with black chairs and a table is visible in the background.
Holiday home in Stonebrook Manor
4.88 out of 5 average rating, 16 reviews

Luxury Vacation Oasis

Hello! Thank you for your interest in staying at Stonebrook Manor in Falmouth 🌴 Near Dunns River Falls, and the cruise port Just a quick reminder: ✔ The base price is for 2 guests, which includes one private bedroom. ✔ Reservations for 3–4 guests include access to the entire home with an additional nightly fee. Please confirm the total number of guests staying so I can ensure the home is properly prepared for your arrival. Looking forward to hosting you! Best regards, Jenise

Guest favourite
A modern kitchen featuring a black countertop with white bar stools positioned along one side. The stools have shiny chrome bases. Natural light enters through a window, illuminating the sleek appliances, including a stove and a microwave mounted above it.
Home in Martha Brae
4.88 out of 5 average rating, 25 reviews

Platinum Paradise Getaway

This 2 bed, 1 bath property is found in the gated community of Holland Estate, approximately 7 minutes away from Chukka Jamaica and about 5 minutes from the Martha Brae Rafting. It is located near the historic town of Falmouth and approximately 25 minutes away from the Donald Sangster International airport. There are also two beaches close to the property ideal for your relaxation. This home is perfect for your next private paradise experience.

Top guest favourite
An infinity edge swimming pool glistens under a clear blue sky, offering expansive views of the ocean and distant shoreline. Sun loungers are positioned along the poolside, inviting relaxation and enjoyment of the breathtaking scenery.
Home in St. James Parish
4.99 out of 5 average rating, 129 reviews

Luxury Oceanview 4BR Villa w/ Balcony, Pool & BBQ

Welcome to BayWatch Villa – a 4BR luxury retreat in Montego Bay. Marvel at breathtaking views of the harbor and Caribbean Sea both day and night. Share unforgettable moments with family and friends. Enjoy spacious living spaces, a modern kitchen, and laundry convenience on premises. Stay connected with Wi-Fi throughout, even by the pool. With solar backup, you’ll always have power for the essentials. Note: AC is not available on backup power.

Superhost
An infinity-edge pool is framed by modern lounge chairs and plush seating. Lush greenery and an expansive lawn create a serene environment, while the Caribbean Sea is visible in the distance under a clear blue sky.
Villa in Montego Bay
4.81 out of 5 average rating, 149 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

Eden Luxe 1 is set on a beautiful hillside offering panoramic views of the sparkling Caribbean Sea. This 2 BR ultra luxurious villa is part of the HOSPITALITYEXPERT Eden Estate, set in the heart of Spring Farm, an upscale Montego Bay community, right above the Half Moon Golf Club. Luxe 1 sleeps up to 6 guests, a private chef is available for hire and we offer pre-stocking services. Includes complimentary access to Tropical Bliss Beach Club.

Guest favourite
A single-story house features a vibrant green exterior with yellow and white striped awnings over the windows. The front yard is well-maintained, showcasing a manicured lawn and surrounding low walls. The driveway is paved, leading up to the entrance of the home.
Home in Falmouth
4.98 out of 5 average rating, 44 reviews

Island getaway

Your family will be safe in this 24-hour gated community and close to everything when you stay at this centrally-located home. 5 minutes to Falmouth town, supermarket, KFC, juicy beef patties, Pizza Hut, Restaurants, 30 minutes to Montego Bay airport, Ocho Rios, Dunn's River Falls, Glistening Water Tours, etc.

Top guest favourite
An open-plan living area features a turquoise sofa with decorative cushions, paired with a dark wood side table. A dining area is visible in the background, along with a well-equipped kitchen. Bright lighting enhances the elegant tiles that reflect the modern decor.
Flat in Montego Bay
4.94 out of 5 average rating, 146 reviews

Island Wish

Island Wish apartment is on the ground floor just steps to the pool. Ideal land space for leisurely strolls or short jogs around the compound. The Secret Hotel is just next door. Taxis are available at the entrance of the Seawind property. Twenty four hours security is provided.

Guest favourite
A spacious retreat is framed by palm trees, featuring a large swimming pool surrounded by lounge chairs. The two-story home displays a mix of traditional architecture with a wide balcony, while manicured hedges and a green lawn enhance the serene outdoor environment.
Home in Martha Brae
5 out of 5 average rating, 6 reviews

The Retreat at Martha Brae (4)

Forget your worries in this spacious and serene space. The Retreat at Martha Brae, is a secluded Home perched on the top of a ridge, overlooking the serene Martha Brae River as well as the Hills and valley's of the World famous Cockpit Country.

Popular amenities for Wakefield holiday rentals

  1. Airbnb
  2. Jamaica
  3. Trelawny
  4. Wakefield