Vacation rentals in Sherwood Content

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Top-rated vacation rentals in Sherwood Content

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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
4.94 out of 5 average rating, 121 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.

Top 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, 207 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.

Guest favorite
Villa in Discovery Bay
4.91 out of 5 average rating, 22 reviews

Ocean-view villa with private pool near beach

Welcome to Villa Amore, a spacious 5-star 3-bedroom villa with pool & stunning sea views! Features: ▪ Fully equipped kitchen & dining area perfect for family sharing. ▪ Spacious living room with direct access to your private pool ▪ Convenient shared guest bathroom Each bedroom offers: ▪ Private en suite bathroom for full comfort ▪ Balcony with stunning pool & sea views Relax in lush gardens with secure parking and just a short walk to Puerto Seco Beach - your perfect tropical retreat awaits!

Guest favorite
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
4.93 out of 5 average rating, 69 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 favorite
A private pool area is showcased, featuring a sparkling blue pool bordered by a stone deck. Lounge chairs in vibrant orange are positioned for relaxation, with a grass-like surface nearby. A decorative wall displays the Villa Di-Nae name, enhancing the overall inviting atmosphere.
Home in Falmouth
4.82 out of 5 average rating, 55 reviews

Villa Di-Nae, The luxury getaway

Nestled in Falmouth, Jamaica, Villa Di-Nae is a true gem that embodies the essence of authentic Jamaican culture, 10 mins away from Martha brae river rafting and 25 mins from MBJ airport. We offer a sparkling pool that beckons guests to take a refreshing dip. The villa boasts an exceptional private chef extra cost dedicated to crafting authentic Jamaican cuisine. Guests are treated to indulge in traditional dishes bursting with flavors Each meal is a celebration of Jamaica's culinary heritage

Guest favorite
Home in Martha Brae
4.95 out of 5 average rating, 39 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)

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, 53 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.

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, 112 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.

Guest favorite
A spacious outdoor area features a swimming pool surrounded by lounge chairs and a covered seating area. Vibrant blue chairs are positioned near the pool, while lush greenery provides a natural backdrop, enhancing the serene environment.
Villa in Duncans
4.93 out of 5 average rating, 86 reviews

Adehya the Villa

Adehya, a Jamaican phrase for "I've arrived" is the quintessential vacation spot in Jamaica. Located in the gated community of Silver Sands Estate, Trelawny, you will have access to the estate's facilities and beaches nearby. Also included in your vacation package is a staff consisting of a housekeeper, butler and a chef. Feeling adventurous? No worries. We can arrange or suggest a list of activities and attractions for you to visit. Adehya is your home away from home.

Superhost
A large swimming pool is surrounded by well-maintained greenery and palm trees. Bright blue water reflects the clear sky, while lounge chairs are positioned around the pool area for relaxation. A signboard can be seen in the background, indicating pool rules and information.
Home in Falmouth
4.91 out of 5 average rating, 53 reviews

Kl Hidden Gem-Ocean view

Bring the whole family to this great place with lots of room for fun. Located 35 minutes from the Montego Bay Airport and 40 minutes away from Ocho Rios, this relaxing retreat will make you feel right at home. We offer 24-hr security along with security cameras on the premises. A swimming pool, gym and jogging trail are some of the amenities offered. All located within 8 minutes is the 876 Beach, Margaritaville, Rafting at Martha Brae and the Falmouth Cruise Pier.

Guest favorite
Home in Florence Hall Village
4.8 out of 5 average rating, 15 reviews

Island Escape @Stonebrook Manor

This spacious (2) bedroom home in a secure gated community offers privacy and peace of mind. Each bedroom has a tv and bathroom for added convenience. Enjoy the fully air-conditioned interior, free Wi-Fi, and bright living space. Relax by the pool or stay active in the state-of-the-art gym. With modern amenities and a tranquil atmosphere, Island Escape is the perfect getaway for families or friends. Experience relaxation and adventure in your slice of paradise!

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
4.99 out of 5 average rating, 132 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.

Popular amenities for Sherwood Content vacation rentals

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