10 Guests

5 Bedrooms

6 Bathrooms

Welcomes: Babies, Children, Toddlers, Pets

3 King, 1 Queen, 2 Twin (can convert into a King). Bed size chart

Outdoor living is encouraged at Windward. Not only do the one and a half acres of enclosed grounds contain carefully landscaped tropical gardens and many secluded benches, but also a magnificent Grecian-style pool. Neighbouring that is a gorgeous deck dotted with loungers and a dining gazebo, and then a pool house containing a wet bar, shower and barbecue. Another building houses the villa’s own air-conditioned gym and garage.

As if all that’s not enough, Windward is part of the Sandy Lane hotel estate, which means guests get exclusive access to this legendary resort’s private beach facilities – before returning to their villa with total privacy and heaps of space. Found on Cooper Hill, the two-storey villa is also only a mile from Holetown’s shopping, spas, restaurants and nightlife.

Inside, the main open-plan living area has French doors to allow light onto pale, chic furnishings and another group dining table. A counter bar leads to the extensive kitchen, with ample appliances used by the cook – part of a full staff who will additionally take care of laundry and housekeeping. The entertainment room contains a large Smart TV and surround-sound system, while all five bedrooms have their own television and rain showers. The master suite, up an elegant double staircase, throws in a bathtub and study for good measure. Two of the rooms feature lengthier California king-size beds, ideal for long-legged guests.

per night


  • Barbeque
  • Garden
  • Gym
  • Handicap Accessible
  • Secure parking
  • Swimming pool
  • Air-conditioning
  • Beach Chairs
  • Beach Umbrella
  • Blender
  • Built-in fans
  • Coffeemaker
  • Dishwasher
  • DVD/Blu-ray Player
  • Freezer
  • Fridge
  • Gated Property
  • Hairdryer
  • Hob
  • Ice Maker
  • iPod Dock & Clock
  • Kettle
  • Maid/Housekeeping
  • Microwave
  • Safe (Bedroom)
  • Satellite or cable
  • Stereo/Sound System
  • Toaster
  • Towels
  • TV
  • Wifi
Show all amenities

Staff & Services

Dedicated concierge

Your dedicated concierge will make sure every aspect of your stay is perfectly tailored to your group’s wants and needs. From arranging transfers and car rental to booking a table at a great local restaurant, we’ll make sure that every second of your stay is perfect.

Home preparation

Each home is carefully cleaned and prepared before you arrive and after you depart.

Meet & Greet

You will be welcomed at the home upon your arrival and helped settle in.

24/7 support

Our team are on hand round the clock, every day of the year, ready to assist. Available from the moment you book to the moment you depart.

Home staff

Property Manager, Cook, Laundress


Approximate location

Essential information

CHECK-IN / check out

Check-in: from 3pm. We'll meet you at the home on arrival at your convenience.

Check-out: by 10am.


We will secure a $2500 security deposit which will be returned once we confirm no damage was caused during your stay.

Why stay with us?

Curated and inspected homes, villas & chalets
Luxury linen and toiletries
Round the clock support
Complimentary weekly clean
Dedicated concierge
Earn & redeem Accor ALL loyalty Reward points
Personal Meet & Greet
Complimentary medical support in partnership with AXA

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