Booking your dream vacation to the Caribbean can seem daunting. Where to go? When to go? Where to stay? What to do? How to do it? Let Prestige Luxury Villas help you take the guesswork out of it with our list of the top six things to consider before planning a trip to the Virgin Islands.


Location, location, location. It’s one of the most important considerations when deciding on the perfect spot for your villa rental. We recommend taking into account the activities you have planned while you’re here, along with other important factors that may influence your decision. For example, if you’re planning any day charters or other boating excursions, staying on the east end of the island near Red Hook provides easy access to many of the marinas in St. Thomas, as well as ferry service to St. John and the British Virgin Islands. On the other hand, if you have a favorite beach – say Magens Bay for example – you might want to stay in a location that is nearby and has a view of its palm tree-lined shore. For shopping, perhaps you would choose to stay closer to all the stores in downtown Charlotte Amalie. If you have a special medical condition, being near the hospital may be a priority. Having a hard time deciding? No need to worry. Since St. Thomas is so small, you’re never really more than a 30-minute drive from wherever you want to be on island.


Next, think about your budget and when you want to visit. How much you spend on your trip depends on the time of year you go. Below is a breakdown of the different seasons and how they rank in terms of price, from least expensive to most expensive:

  • June 1 – October 31

This is the most affordable time of year to visit since it’s hurricane season. While you can find great deals on accommodations and flights during this timeframe, we do recommend safeguarding your vacation with trip insurance. If your stay is affected by storms, we will work with you to get it rescheduled with no penalty.

  • January 6 – May 31

The first part of the year, or winter/spring break season, is the next least expensive time period to travel to the island.

  • High Season: November 1 – 31
  • Peak Season: December 1 – January 5

During high and peak seasons, prices for accommodations and airfare are higher and the island is more crowded, so you need to allow a longer lead time when booking excursions or making restaurant reservations and other plans.

While the above information provides general guidance, we encourage you to work directly with your reservationist, as they may be able to identify special pricing during certain times of the year or find something that’s not readily available to suit your needs.


It’s always helpful to check out reviews of a property before booking. If you don’t see any reviews for a specific property on our site, please be sure to ask your reservationist. They’ll be able to send you a link to reviews. Unfortunately, due to the policies of companies such as Airbnb and VRBO, it’s impossible to transfer listings between hosts. Therefore, if the villa changes manager position, even if it had great reviews, none of them transfer to the new listing.


It’s important to know who your host is, how much experience they have, and how long the company has been around for. At Prestige Luxury Villas, we’re proud to offer more than 40 years of local, in-depth, on-island knowledge and expertise. We offer a complimentary, full concierge service that is constantly being updated with the newest and best things to do, see and experience on St. Thomas. Not only that, but you’re just one phone call away from a live person who can help.


Instead of using Airbnb or VRBO, when you book directly with us, you can save anywhere from eight to 20 percent, depending on the time of year and which property you choose. We also provide:

  • Cancellation policies similar to other sites
  • Personalized service
  • 24/7 emergency response

Lastly, when planning your visit, consider the length of your stay prior to making your reservations. You’re taking the time off work and spending the money to get here, so you might as well make the most of it, right? Remember that the longer you stay, the more likely you’ll be able to negotiate additional discounts for your accommodations. Most villas require a minimum stay of five or seven days, depending on the time of year. Plus, there’s so much to do in the VI that you could easily stay 10 days or even two full weeks and do something different every day.

What are you waiting for? Let us help you plan the dream vacation of a lifetime. Call us today at 1-888-609-9333 or email us at

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