Holiday rentals in Sherwood Content

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Top-rated holiday rentals in Sherwood Content

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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, 195 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, 111 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
4.85 out of 5 average rating, 136 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
A bright blue door stands open, offering a view of the clear turquoise water and distant boat on the horizon. Lush greenery frames the entrance, enhancing the connection between the interior space and the inviting beach just outside.
Cottage in Runaway Bay
4.94 out of 5 average rating, 128 reviews

Bahia - Charming seaside cabin, loft/wood shutters

Bahia is a 1 bedroom cottage located directly on a beautiful beach which is perfect for swimming.* Ideal for a couple, or a family with children who can be accommodated in a loft. Beachside patio with hammocks and outdoor furniture. Air-conditioned and fans. Cook included. Nightly security guard. 50 minutes from MBJ Airport. Popular attractions nearby. A truly memorable, rejuvenating beach holiday. $300 per night for 2 persons, for additional persons see below. *Beach/water subject to weather

Superhost
Villa in Discovery Bay
4.78 out of 5 average rating, 32 reviews

10 min to Runaway Bay Beach-Full Kitchen-BBQ

Set on 44,000 ft² / 1-acre in Discovery Bay, 3 min → Bengal Beach (15 min walk) ✓ Superhost care + 4.8★ average, 29 reviews ★ Extremely safe, community ✓ Free early check-in ✓ 1 hr ✈ Montego Bay Airport (MBJ) ✓ Dinning table for 6, family gatherings welcome ✓ Full equipped + Stocked kitchen ✓ Flexible visitor policy ✓ Surround sound in ceiling ✓ Rooftop terrace, outdoor seating & treetop views ✓ Meals by in-home chef available ★ “The rooftop seating provided a great view of the greenery.”

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, 114 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.

Top guest favourite
A spacious bathroom features a large black Jacuzzi positioned on a multi-step platform, surrounded by glossy black and white tiles. Natural light filters through an arched window dressed in bright yellow curtains. A standing shower is visible, along with a sink and elegant wall-mounted mirror.
Home in Runaway Bay
4.95 out of 5 average rating, 146 reviews

Cambridge mi casa ur casa w/pool & beach access

We offer newly- renovated comfortable two- floor apts in a friendly safe community overlooking CARDIFF HALL Beach in the Resort Town of Runaway Bay in St. Ann Jamaica ▪️No need to worry about security / safety because there are 24 hour surveillance camera and host lives on property ▪️We offer one 1bdr & 2br ▪️Price starts from 100US for 2 guests and increases by 30US per additional guests ▪️We are about 1hr away from the Sangsters International Airport ✈️ 25 mins from Ocho Rios

Top guest favourite
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
4.89 out of 5 average rating, 201 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
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, 104 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 private pool featuring illuminated water jets creates a relaxing ambiance. Surrounding the pool, lounge chairs invite comfort, while colorful lights accent the area, adding a vibrant touch to the tranquil setting.
Home in Trelawny Parish
4.85 out of 5 average rating, 53 reviews

NC Cozy Estate with Private Pool, AC, & WI-FI

Escape to your own private slice of paradise. This tranquil getaway is ideally located just 2 minutes from Ocean Coral Spring Resort and 30 minutes from Sangster International Airport. Top attractions include rafting on the Martha Brae River, horseback riding, and ATV experiences. The lively Falmouth Pier is only a 7-minute drive away for dining, shopping, and entertainment. A comfortable space designed for relaxation, complete with essential amenities including reliable hot water.

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, 44 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.

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, 126 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 holiday rentals

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