Vacation rentals in Sherwood Content

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Top-rated vacation rentals in Sherwood Content

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Guest favorite
Villa in Runaway Bay
4.95 out of 5 average rating, 38 reviews

Ocean View • Pool • Pickleball • Gated | For 12

Welcome to Villa Palaav - A modern oasis in a private gated community Perfect for: • Birthday trips • Bachelor/Bachelorette groups • Family reunions • Friends trips • Retreats 🎉 Celebration Pkgs starting at US$350 This 6-bedroom Ocean View Villa features three 2 bedroom, apt-style King suites, each with private kitchens, 1–2 bath, and open-concept living areas, solar power, rainwater harvesting & smart cooling Amenities include: • Private pool • Pickleball court • Billiards room • Mini golf

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, 210 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
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

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, 122 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
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, 70 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
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
A spacious swimming pool is surrounded by lush landscaping, featuring comfortable lounge chairs along the water's edge. The pool is complemented by a well-appointed building with multiple windows and a welcoming entryway. Additional amenities are visible, enhancing the outdoor leisure experience.
Vacation home in Stonebrook Manor
4.9 out of 5 average rating, 21 reviews

Tropical Escape: Spacious 2-Bedroom Vacation Oasis

Bring the whole family to Stonebrook Manor just 25 minutes from Montego Bay Airport! Explore nearby attractions like Martha Brae Rafting Village, Luminous Lagoon, Falmouth Swamp Safari, Blue Water Beach Club, and Rio Bueno Tubing Safari. Iconic spots like Doctor’s Cave Beach, Margaritaville, Green Grotto Caves, Dunn’s River Falls, and Blue Hole are within reach. Located in a gated community with free parking, my home is the perfect tropical retreat. Relax, unwind, and create memories!

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.

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, 54 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
An infinity pool reflects the vibrant blue sky, surrounded by palms. Sailboats float peacefully in the water, with tropical villas visible in the background. The scene captures a calm, inviting atmosphere, enhancing the connection between the pool and the waterfront.
Townhouse in Montego Bay
4.91 out of 5 average rating, 70 reviews

Caribbean 4br Ocean Retreat Pool Gym Walk to Beach

Welcome to Stay Awhile, our modern Caribbean family villa where a private oasis awaits you. Feel right at home in a beautiful open space that flows into a perfect combination of indoor/outdoor tropical living. Highlights - Infinity Pool * Private Beach Access * Gym * Kids Play Area * Housekeeping * Gas Grill/BBQ * Gated Waterfront Community * Chef/Cook on request * Spa Services

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
4.92 out of 5 average rating, 84 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.

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