Holiday rentals in Sherwood Content

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Top-rated holiday rentals in Sherwood Content

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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, 198 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 in Duncans Bay Beach
4.94 out of 5 average rating, 115 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.

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, 146 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

This property has electricity, water and internet. 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
Home in Martha Brae
4.94 out of 5 average rating, 35 reviews

Haven Escape near Montego Bay

Holland Estate is a 24 hours gated secured community *30 Mins from Sangsters Int'l airport Montego Bay, Pier 1, Margaritaville+ more *1 hr from Ochi Rios ,Dunns River Falls, Mystic Mountains +more *5 mins from Rafting on the Martha Brae River, Falmouth Mystic Lagoon, Chukka Adventures +more * 10 mins to beaches, restaurants, cruise ship pier. This cozy & peaceful semi-attached studio is equipped with Air Conditioner & Ceiling Fan, Water Heater, Wifi, Smart TV with Netflix(use own log in)

Superhost
A serene beach view is presented, featuring a wooden gazebo on the sandy shore beneath a clear blue sky. The gentle waves of the turquoise sea are visible, framed by lush greenery, creating a tranquil and inviting atmosphere for relaxation.
Home in Duncans
4.86 out of 5 average rating, 117 reviews

ViILLA BY THE SEA, Steps to Beach, cook included.

Yellow Canary Villa is spacious, light and airy with a modern decor. The living room opens out onto a patio area and the garden. A few steps away is our beautiful beach which is lined with almond trees for shades. Leroy's bar, cafes & craft shops are a short walk. Duncans Town is 5 mins. by taxi. There are restaurants, supermarkets, fruit stalls, a ATM and taxis to various locations. MontegoBay Resort &Airport is just 40 minutes by transport &Ocho Rios is approximately the same distance.

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
4.87 out of 5 average rating, 47 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
Bungalow in Laughlands District
4.88 out of 5 average rating, 205 reviews

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

Top guest favourite
Home in Falmouth
4.94 out of 5 average rating, 33 reviews

Island Oasis Stonebrook Vista

Welcome to Island Oasis! Centrally located vacation home with stunning mountain views, front patio, rooftop deck and 24-hr security. Guests have the option to book 2 or 3 bedrooms.The modern open-plan living area boasts natural light and high ceilings enhanced by contemporary themes throughout the space. We offer complimentary snacks and a Netflix subscription. Island Oasis is designed to bring true comfort and relaxation to our guests. Your host, Salkey & Nicollette

Guest favourite
An infinity-edge swimming pool is shown, reflecting the clear blue sky and offering stunning views of the ocean and city. Sun loungers are positioned on the surrounding patio, inviting relaxation in a serene atmosphere.
Home in St. James Parish
4.99 out of 5 average rating, 127 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
A refreshing outdoor pool is framed by a stone deck, featuring lounge chairs positioned around its perimeter. Lush palm trees sway gently in the breeze, and blue skies are dotted with a few clouds, creating a serene atmosphere.
Home in Florence Hall Village
4.84 out of 5 average rating, 116 reviews

Oasis at the Manor w/ King Bed, shared pool & gym

Step into a beautiful 2-bed/2-bath home adorned with modern transitional decor, crafting the ultimate sanctuary for rejuvenation and tranquility. Indulge in this modern oasis boasting black stainless-steel appliances, smart TVs, a serene front door patio, and a cozy backyard gazebo. Enjoy countless scenic views within a secure, gated community with 24-hour security. Community perks include a pool, gym, clubhouse, and scenic walking trail.

Guest favourite
Guest house in Spring Garden
4.9 out of 5 average rating, 10 reviews

Exclusive Mountain & Farm Villa Escape

Expect an Authentic Experience high in the mountains of Jamaica: Imagine waking up to the gentle sounds of nature, the fresh mountain breeze carrying the scent of ripening fruits and morning dew over rolling farmland. Nestled in the lush, green hills of Trelawny, this two-bedroom, two-bathroom home offers a perfect escape into nature, and authentic rural Jamaican

Guest favourite
Home in Martha Brae
5 out of 5 average rating, 15 reviews

The Retreat at Martha Brae (6)

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 Sherwood Content holiday rentals

  1. Airbnb
  2. Jamaica
  3. Trelawny
  4. Sherwood Content