Vacation rentals in Sherwood Content

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Top-rated vacation rentals in Sherwood Content

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Guest favorite
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, 200 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 favorite
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, 116 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 favorite
Two large cruise ships are anchored offshore, visible against a backdrop of gray, cloudy skies. The waters reflect a muted palette of blues and greens, while the shoreline is dotted with lush vegetation. The scene captures a tranquil coastal atmosphere.
Home in Falmouth
4.84 out of 5 average rating, 19 reviews

Coastal Living, Sleep 4, Falmouth, Jamaica

Reconnect with nature at this unforgettable escape. Enjoy the feel of the island breeze in a cozy ranch home. This space is clean, relaxing, and designed for easy living. No unicorns or fake swans. Rather, we offer great comfort, giving you the best bang for your dollar. This home offers 2 bedrooms/2 bathrooms in a quiet gated community, equipped with pools, etc. The Falmouth area beaches are within walking distance. The city of Montego Bay and the Montego Bay airport are in close proximity.

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 favorite
Home in Martha Brae
4.94 out of 5 average rating, 36 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 charming entrance is showcased with a white picket fence and a gated entry, offering a glimpse of lush greenery and palm trees surrounding the property. The house features a gabled roof and a spacious front area, inviting guests into a serene environment.
Home in Duncans
4.86 out of 5 average rating, 118 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 favorite
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 favorite
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
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 favorite
A modern living area is presented with a large sectional sofa adorned with decorative pillows. A marble-topped coffee table occupies the center, with a vase of sunflowers adding a cheerful touch. The room is illuminated by soft natural light filtered through elegant wooden blinds.
Home in Falmouth
4.98 out of 5 average rating, 110 reviews

Villa Renee'

This modern eco friendly house is your perfect getaway space offering comfort, 24 hrs security and tranquility. The property is in close proximity to the highway which makes it the ultimate vacation location/home. All the best attractions on the islands north coast are minutes away (Glistening Waters, Green Grotto Caves, 876 Beach, Burwood Beach, Pueto Seco beach, Dunn's River fall's, Dolphin Cove, Chukka Adventure Park and many more). Perfect for family, friends or work travel.

Top guest favorite
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, 128 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.

Guest favorite
Guesthouse 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 favorite
A stylish living area is displayed with a sectional grey sofa, decorated with orange accent pillows. A flat-screen TV is mounted on a wall featuring built-in shelving with decorative items. A coffee table holds a magazine, with a glimpse of the kitchen in the background.
Home in Falmouth
4.91 out of 5 average rating, 77 reviews

SL Retreat 1 King size bed Entire Apt

Kick back and relax in this calm, stylish space. Get a good night sleep in a king size bed and pull out sofa bed. Hot water solar heater for your hot showers. 5 minute drive to the beach, great restaurants and grocery store, famous Falmouth Market every Wednesday. 24 hour security gated community. Stonebrook Vista is the name of our gated community.

Popular amenities for Sherwood Content vacation rentals

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