The Old Windward Villa

tobago, caribbean
4 bedroom - 6 bath
(0 reviews)
Travel dates:
$875 per night (USD)
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This idyllic villa in Tobago in the West Indies offers casual luxury at every turn and is a fantastic respite from busy city life. Sleeping 8, Old Windward is a wonderful way to take your extended family on vacation or for families traveling together. Relax in the property’s hammock or the whirlpool while the kids play in the two infinity-edge pools. The onsite staff is also happy to prepare dinner for the whole family. In the morning, explore the island with the kids, where you can visit the island’s renowned rainforest or take in the local waterfalls. Bird watching and deep-sea fishing are also available. Round out your days by relaxing at the villa with game nights in the open-air living room.

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  • Air Conditioning
  • Baby Bath
  • Baby Monitor
  • Babysitter / Nanny
  • Backyard / Garden
  • Balcony
  • Bathtub
  • Bed Rails
  • Bicycles
  • Cabinet Locks
  • Changing Table
  • Chef / Catering
  • Children's Dinnerware
  • Corner Guards
  • DVD Library
  • DVD Player
  • Dishwasher
  • Elevator
  • Fireplace Guards
  • Game Console
  • High Chair
  • Housekeeper
  • Outlet Plugs
  • Parking
  • Pet-friendly
  • Pool
  • Pool Gate
  • Stair Gates
  • Television
  • Toys / Children's Books
  • Washer / Dryer
  • Wifi
  • Window Guards
4 full / double

What we love

  • Balinese architecture resembling a village of miniature houses perched on a bluff
  • 180-degree views of the Atlantic Ocean, along with the villa’s unique alignment with the trade winds, which keeps the entire house cool and comfortable
  • 4 bedrooms that wrap around a large sun deck
  • Each bedroom has large windows, soft linens and a convenient ensuite bathroom
  • Outdoor shower area near the koi pond and infinity pools
  • The garden filled with tropical flowers and fruit leads to a small sandy cove
  • Vast living room is open to the bay, allowing ocean breezes in, and has teak day beds and armchairs for afternoon naps
  • Open-plan, fully-equipped kitchen has two refrigerators and large windows that look onto the sandy beach below
  • Barbecue area next to the villa’s large kitchen

Things to know

  • Please note that the rate is based upon occupancy and the host should be contacted to confirm pricing for your party
  • 20 minutes from Crown Point Airport by car
  • Private aromatherapy massage, meal service and grocery delivery available for additional fees
  • Board games and a DVD/CD library are available
  • Air conditioning and fans in each bedroom
  • The pool is unheated and ungated
  • Small pets may be allowed but on a case by case basis
  • There is a nearby grocery store 10 minutes away by car
  • Baby and child equipment available upon request
  • 1 house manager and 2 housekeepers included in the booking

Property perks

  • Concierge
    A concierge service is available for this property
  • Baby rental
    equipment partner
    We work with a carefully-chosen baby equipment rental partner in this location
  • Kid & Coe
    Kid & Coe Select properties have been visited by our team and checked for their suitability for family travelers
  • Itinerary
    We provide a family-focused itinerary for properties in this destination
  • Professional
    This property is professionally managed by a trusted partner
Aries B.
Member since May 23, 2014
I manage our family home Ohana Villa and try to fit in as much snowboarding, rock climbing, surfing and ping pong into my life as possible. I have Tobago roots through my mother's family, and am busy bringing up my family in the South of France.

Tobago, Caribbean

Stop: hammock time

Tap your feet to the plink-plink of the steel-drum, watch local fisherman haul in their silvery catch on wooden jetties, and snorkel through coral wonderlands. This is the gruelling life in Tobago, where you’ll find picture-postcard beauty around every corner and far more hammocks than hassle. With less night-life than Jamaica, no five-star resorts like Barbados and more of a holiday vibe than hardworking Trinidad, Tobago is the laid-back, go-slow island of the Caribbean, with rustic infrastructure, fringes dotted with fisherman’s cottages untouched by commercialism and a superb coastline. Spot exotic birds in tropical forests, shadow giant turtles in the sea or find your own Nemo among the clownfish in the corals.