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Your Winter Getaway…5 Factors for Thought


As the cold wintery weeks roll in, you begin to yearn for the warmth of a Caribbean getaway – bare toes in hot sand, less clothes, and a sexy tan….

However, before you can get that tan that will invoke the envy of your snow-bound friends, you must first choose a vacation rental property.

Whether you will be vacationing with children, or your party consists of adults only, the perfect home-away-from-home should tick all the boxes on your group’s wish list.

Here are some points to consider when choosing a vacation villa:

  1. Location: Beachfront, hillside, private estate, or in-the-heart-of-town, the location of the villa is important. If one of your must-haves is a swinging night-life, then you want to be close to a town. If you relish the cool trade-winds and amazing views, then a villa that is elevated on a hillside is for you. Once you have short-listed a property, determine its exact location on the island by using Google Earth.
  1. Budget: Winter/High Season is a period of demand for vacation properties, so expect to pay higher nightly rates. It is not customary that villas advertise specials or discounts on winter rates, but in most cases if you book directly with the owner or island manager, you can enjoy perks such as complimentary transfers or even a discount off the advertised rate. You should always ask for the Free Night in Paradise Special. If granted, you will pay for 6 nights and enjoy the 7th
  1. Amenities: Luxurious linens, water sports equipment, provisioning, free WiFi, and daily housekeeping. While most high-end villas will include the cost of these amenities in their rack rate, expect to pay for added services such as in-villa massages, chefs, baby-sitting, or ground transfer. Ask about a Meet & Greet service so finding the villa on your first arrival is easy. The island manager will provide this service and introduce you to the features of the property on arrival.
  1. Booking Process: You will find details of the same villa on numerous rental websites. While all rental sites will advertise the same rates, try to inquire for availability and rates directly through the villa-owner’s website. Your inquiry will be fielded by the island manager, who holds the most updated rental calendar. They will issue the invoice and contract if you do decide to book. Expect to pay 50% of the rental value on confirming the reservation and the balance 45 to 60 days before your arrival. If you have children in your party, expect to complete a Liability Waiver.
  1. Concierge Services: This is one of the perks of staying at a villa as opposed to a resort. The villa comes with an Island Manager who acts as your personal concierge and will assist in arranging travel, transportation, itineraries, reservations, and activities. This free concierge service means you can enjoy your vacation like a celebrity, with every detail of your stay pre-arranged for you.


So, if you have been dreaming of that perfect island vacation; one week in the warm Caribbean, where instead of shoveling snow, you have to wiggle-dance the sand from your swimsuit, choose a vacation villa with these five factors in mind and enjoy days of sunshine, warm seas, and friendly, helpful islanders.

Smiths Gore

Smiths Gore

Smiths Gore is one of the preeminent real estate advisers in the British Virgin Islands and the Caribbean. Contributing authors include Kate Henderson, Morgana Tilling, Bernadette George, and Lucienne Smith
Smiths Gore

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