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Sleeps: 10 Bedrooms: 5 Bathrooms: 6


Wow Factor
Ideal for Kids Walk to Beach Walk to Village All Bedrooms En-Suite

Early Bird 2021

Book your 2021 villa holiday by the 28th February and receive:
•    Welcome Hamper on Arrival
•    Up to £100 Private Chef Voucher
•    Free change on dates if restrictions mean you can't travel
•    Ts&Cs apply

\Windward is a ten-person villa sits on a fully enclosed private estate with its own outdoor pool, in the desirable West coast of Barbados, just ten minutes from the beach. At Windward guests experience the privilege of full access to the highly desirable Sandy Lane Beach Club with an incredible selection of complimentary facilities and amenities.

On entering Windward through the main entrance foyer, a beautifully designed double staircase finished with wrought iron railings leads upstairs to the stunning Master Suite, study and two additional bedrooms. The architecture and décor of Windward is wonderfully lavish, and no expense has been spared in the decoration of this incredible Caribbean villa rental.

Relax on any one of the beautiful terraces and enjoy views over the 1.5-acre tropical gardens, or walk around and discover the many secret seating areas where you can hide away in this natural paradise.

Among the many assets of this villa are the five double en-suite bedrooms, with plenty of space and balconies, there’s also large dining spaces both inside and out. The large kitchen has ceiling fans and is fully equipped with professional equipment, marble finishes and a breakfast bar. Adjacent to the kitchen is a laundry area and staff facilities.

In a separate out-house you’ll find the professionally equipped gym, with treadmill, upright bike, elliptical machine and free weights. The gym is air-conditioned and features professional standard equipment including treadmill, upright bike, elliptical machine, multifunction exercise machine and free weights. There is also a powder room by the main foyer. The main living area is open plan, with French doors extending the length of the room which, opening onto the spacious covered veranda, creating an expansive space for combined indoor/outdoor entertaining. Steps from the main veranda lead out to the garden and pool.

The spacious Master Suite features a king-sized bed, large walk-in closet with dressing area and mahogany floors. Multiple French doors span the length of the bedroom, opening out to a gorgeous patio with table & chairs for relaxed lounging. Adjoining the Master Suite is an air-conditioned study (which can be converted to a small nursery if required) with a large computer desk and small fridge. The impressive en-suite bathroom includes a tub, large rain shower and double vanity with marble finishes. Bedroom Suite Two features a Queen bed and French doors opening out to a private covered patio with table & chairs and a view of the pool and gardens. Bedroom suite Three has a California King bed, with garden views. Bedroom suite Four, on the ground floor, has two extra-long twin beds that can be converted to a King if required. French doors open onto a covered patio with steps leading directly to the pool area. Bedroom suite Five has a California King bed with garden views. All bedroom suites are air-conditioned with ceiling fans, safes and cable television. The en-suite bathrooms feature marble finishes, double vanities and rain showers.

Windward has two dining areas that each comfortably seat ten. Indoor, the formal dining room is supported by a serving area that contains a sink, ice machine, small fridge and iPod dock/entertainment system. The media room is air-conditioned and features a multimedia 50” Smart television with surround sound, two comfortable sofas and a desk.

Windward sits in over 1.5 acres of carefully landscaped grounds featuring “secret” sitting areas with benches for guests to escape and relax in the spectacular tropical gardens.

The outdoor dining gazebo, accessed via a short-covered walkway, features a circular coral stone dining table and views of the beautifully landscaped gardens. A large coral stone deck surrounds the pool area and features comfortable sun loungers, umbrellas along with table and chairs. The pool house encompasses a covered bar area, barbecue and bathroom facilities including a shower.

A team of expert staff are included in the rental and are on hand to offer as little or as much assistance on your holiday as you desire.

Oliver Approved

What you should know…

  • The nearest beach is 5 minutes away by car
  • The whole property doesn't have step-free access

Property Features

Private Pool Wi-Fi/Internet Air-Con BBQ All Bedrooms En-Suite Ground Floor Bed & Bath Cable TV Wheelchair Access Gym/Fitness Room DVD Ceiling Fans

The Villa

Windward is a truly impressive and lavish 5-bedroom villa that has its own dedicated staff, swimming pool and fitness area.

Ground Floor
- King bedroom, with en-suite bathroom
- Twin bedroom, with en-suite bathroom
- Communal bathroom
- Dining & living area
- Fully equipped kitchen
- Media room
- Study
- Utility room

First Floor

- Master bedroom, with en-suite bathroom
- King bedroom, with en-suite bathroom
- Queen bedroom, with en-suite bathroom & balcony

- Fitness area

- Private swimming pool, with Roman steps access
- Barbecue
- Gazebo
- Lawn area
- Outdoor dining & furniture
- Parasols
- Private Parking
- Sun loungers


About the surrounding area of Windward
Walk to Beach Walk to Village Walk to Restaurant <1hr to Airport Watersports Golf Nearby Tennis Nearby Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages
Loading map

Windward is located on the glamorous west coast of Barbados, very close to Sunset Crest and Holetown, where there is duty free shopping, fine dining/restaurants, coffee shops, Limegrove Lifestyle Centre and the vibrant night time scene on 2nd Street.

There is golf and tennis available on the Sandy Lane Estate and can be organised by your villa manager.

Guests at Windward have exclusive access to the Sandy Lane Beach Club (5 minutes away by car), with private and secure parking. Services at the Beach Club include beach loungers, umbrellas, complimentary wifi internet and bathroom/shower facilities. There is a full bar on site where drinks, lunch and light snacks can be purchased. Alternatively, if guests prefer, the cook can prepare a picnic lunch packed in a cooler for your day at the beach.

Local Amenities
Nearest Airport Grantley Adams International Airport BGI


Nearest Town/City Holetown

(Walking Distance)

Nearest Restaurant

(Walking Distance)

Nearest Bar/Pub

(Walking Distance)

Nearest Beach

(Walking Distance)

Nearest Golf

(Walking Distance)

Nearest Tennis

(Walking Distance)

About the Island & Getting There

About Barbados

At first glance you could be mistaken for thinking that Barbados is purely a beach holiday destination, but you're urged to reconsider this common belief. The island of Barbados is peppered with astonishing landscapes (both coastal and inland), enchanting locals, sublime cuisine, intriguing rums, fascinating wildlife, symbolic architecture and a selection of striking holiday villas.

Delve deep into the history of the island and start your holiday by visiting Sunbury Plantation House & Museum. This former plantation was built in 1660's and the premises are scattered with antiquities that delicately detail a recent history of Barbados. St. Nicholas Abbey also provides an insightful representation of Sugarcane production, Bajan artefacts and a wonderful observation point at Cherry Tree Hill. If you’re keen to visit one of the oldest Parliamentary buildings within the Commonwealth and appreciate the democratic legacy of Barbados, drop by The Parliament Buildings. This neo-gothic congress can be found in Bridgetown and act as a representation of Barbados’s Independence. There is so much history present throughout the island and as a result, Bridgetown and its Garrison has been declared a UNESCO World Heritage site, which the locals are very proud of.

Great efforts have been made to persevere the natural beauty of Barbados, so if you’re drawn to the exploration of National Parks and multicoloured gardens, it won’t take you long to realise that Barbados is a haven for such paradises! Within the Andromeda Botanic Gardens, Farley Hill National Park, Flower Forest, Hunte's Gardens and Welchman Hall Gully - visitors, and Botanist alike, will be lost for hours admiring these astonishing botanical parklands. Keep an eye out for the Dwarf Poinciana, or Peacock Flower…it’s the national flower of Barbados.

Bajan’s take their food very seriously! If you and your fellow travellers are enticed by the gastronomic aspect of holidaying, we believe you’ve selected the right island. With every aspect of cookery mastered; from pickling to freshly prepared dishes, sweet & savoury, fragrant & spicy and of course, the bountiful choice of seafood. Check out the food stalls in Paynes Bay Church – where vendors exhibit locally made dishes & street food that will scintillate the taste buds. At the end of every working week, locals and tourists both flock to Oistins, for 'Fish Fry Day'. This is a must for those who haven’t undergone the experience! The evening starts with barbecues and then ascends into a joyful party. This caps off a busy few days of work for locals as well as the 'strains' associated with serious holidaying.

Barbados is of course iconic for its Beaches & Rum…so why not bring them together? You will have to go out of your way not to be able to find a beach bar along the west coast of the island, as well as the countless Rum Shops. Yes, you’ve read correctly, Rum Shops! These small and locally run businesses embrace the Bajan spice of life, in liquid form. Very delicious! If you’re searching for something a little more special, take a trip to the east coast and visit Sand Dunes Bar and Restaurant at Windy Hill, for an unforgettable experience.

Barbados is a distinct and striking part of the Caribbean. It’s a great fit for all types of travellers, as the island really does have it all. For a little more information about this delightful island, check out our guide to a remarkable stay!

Prior to Booking

Please be aware that Barbados is an island nation that experiences weather patterns dictated by the Atlantic Ocean to the north of the island and the Caribbean Sea to the south of the island. This tropical rainforest climate results in the island experiencing a hurricane season, which usually occurs between June to November. When thinking about booking your holiday to Barbados Republic, please consult Foreign travel advice for more information.

Entry Requirements

Tourists who are British Citizens will not require a visa upon arrival and Departure Tax is included in most flight costs. Please check Entry Requirements before departure.

Local Public Holidays

21st January - Errol Barrow Day
28th April - National Heroes Day
1st May - Labour Day
10th June 2019 - Whit Monday
1st August - Emancipation Day
First Monday of August - Kadooment Day
30th November - Independence Day

Getting There

Barbados is served by Grantley Adams International Airport in Bridgetown.

From the US:
Direct flights are available from Charlotte, Miami and New York with AA, JetBlue and US Airways.

From the UK:
Direct flights are available from London on BA and Virgin Atlantic. Chartered flights are also available from several other UK airports.

Grantley Adams International Airport, Christ Church, Barbados:

View large map


Best Suited For: All Ages
Ideal for Kids Ideal for Teens Ideal for Xmas/NY

If you’re travelling with kids, riding in a 4x4 Jeep Safari across the island is bound to go down a treat. The full-day tour is led by a professional guide and is a family-friendly way to see Barbados. During the tour, you’ll discover the local history, culture and environment while getting up close and personal to the beautiful landscapes. Some of the locations visited during the tour include Little Bay, Joe's River Forest, Bathsheba, and Edge Cliff. A traditional Bajan buffet lunch is provided as well as hotel pickup and drop-off at select homes.

The beach is just a 5-minutes away from Windward, so why not take advantage of having access to the Sandy Lane Beach Club facilities and enjoy a day out by the sea. Also visit Folkestone Marine Park, which is less than 10 minutes away by car. The children will love snorkelling in the calm waters here and spotting all sorts of colourful fish. There’s also a playground and a museum with aquariums to browse.

Baby and Toddler Equipment

  • Cot(s)
  • High Chair(s)

Kids Activities Close-by

  • Beach Nearby
  • Walk to Beach
  • Walk to Village
  • Walk to Restaurant
  • <1hr to Airport
  • Watersports
  • Tennis Nearby
  • Horse Riding
  • Outdoor Pursuit & Activities
  • Tourist Towns & Villages

Onsite Facilities

  • DVD

Services Available

  • Chef/Cook Available
  • Maid Service Available


Oliver's Extras

  • Chef/Cook Available
  • Maid Service Available
  • Security guard
  • Gardener Available
  • Pre-arrival Groceries Available
  • Sandy Lane Property Owners Beach access Included

At Oliver’s Travels we pride ourselves on going that little bit further for our guests. From private chefs to babysitters we can help you arrange those little extras that make it a truly memorable holiday. Simply fill in the concierge request form or contact the Oliver’s Concierge Team who will be happy to help. We can typically help you arrange any of the following:

- Maid service/extra cleaning
- Private chef/cook/catering
- Welcome hamper/pre-stocked fridge
- Local day-trips or tours
- Airport pick-up/drop-off
- Babysitting/childcare services

Simply fill in the concierge request form or contact the Oliver’s Concierge Team.

Please note that all extras are subject to availability and must be requested in advance of the holiday (prices on request). Due to some rural/remote locations, not all services will be available at all properties. However, we will always do our best to fulfil your requests!

Terms & Conditions

Villa Conditions
- Prices may be subject to local taxes and service charges where applicable and may change without notice.
- Holiday rates may vary.
- A 50% Client Deposit may be requested during Festive Bookings.
- Villa availability is structured on a Request Basis, so please enquire with our Consultants when booking a Holiday

These terms and conditions may be amended from time to time.

Security deposit A Credit Card Charge Authorisation/Security Deposit to be requested upon arrival. Applicable refunds will be credited 14 days after departure.
Arrival time 3.00 p.m.
Departure time 12.00 Noon
Energy costs included? Included in the rental price
Linen & towels included? Included in the rental price
End of stay cleaning included? Included in the rental price
Tax A 7.5% Government Tax & 2.5% Government Room Levy (calculated based on nightly rate) to be collected at time of booking. Additionally, a 1.5% Service Charge will also be included.
Changeover day Flexible
Minimum stay 14 nights between 20/12 - 10/01, otherwise 7 nights
Internet access? Wi-Fi connection included
Pets welcome? Pets are not allowed
Smoking Allowed? Smoking & Vaping is not permitted inside the villa
Insurance It is recommended that all guests take out insurance to cover against potential cancellation and any accidental damage caused during your stay at the property.
Other Ts and Cs Toddler & Baby Equipment available upon request
Other 2 Pre-arrival Groceries are subject to 15% Service Charge + VAT

Rental Rates

Please note: All rates below are subject to 11.5% Shared Economy Levy & Service Charge

Prices based on an occupancy of 10 people:

Rental period Weekly
Jan 15th 2021 - Apr 16th 2021 £21,774
Apr 16th 2021 - Dec 15th 2021 £15,633
Dec 15th 2021 - Dec 20th 2021 £21,774
Dec 20th 2021 - Jan 11th 2022 £29,032
Jan 11th 2022 - Jul 19th 2022 £21,774

Prices based on an occupancy of 10 people:

Rental period Weekly
Jan 15th 2021 - Apr 16th 2021 €23,023
Apr 16th 2021 - Dec 15th 2021 €16,529
Dec 15th 2021 - Dec 20th 2021 €23,023
Dec 20th 2021 - Jan 11th 2022 €30,697
Jan 11th 2022 - Jul 19th 2022 €23,023

Prices based on an occupancy of 10 people:

Rental period Weekly
Jan 15th 2021 - Apr 16th 2021 $27,983
Apr 16th 2021 - Dec 15th 2021 $20,090
Dec 15th 2021 - Dec 20th 2021 $27,983
Dec 20th 2021 - Jan 11th 2022 $37,310
Jan 11th 2022 - Jul 19th 2022 $27,983

Please note that prices may not be 100% accurate for dates outside of the current calendar year. For an accurate quote, please enquire.

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