6 Steps to Booking Your Ultimate Vacation Rental

6 Steps to Booking Your Ultimate Vacation Rental

Ultimate VI Vacation Rental
This property available through: St.John Ultimate Villas

Accommodations typically represent the biggest expense of your VI vacation, on average around 50% of your budget (depending on group size, location and accommodation style). It’s a good idea to get a jump start on finding your accommodations ASAP so you know your options and can book the best VI vacation rental for you.

Our local accommodations experts recommend that you follow these 6 steps:

1. Start Now

It’s not unheard of to book a year in advance. If you only have a narrow window of time to visit the Virgin Islands school vacation, wedding or a specific island holiday or it’s during peak season Dec 15-April 15, booking well in advance is vital in securing the best vacation rental you can get.  If you wait too long, you’ll have fewer options and may end up paying more for less. The earlier you begin the more options you will have that will balance price with the features you want.   Besides, it’s FUN to plan and virtually explore one of the most beautiful regions on the planet before you get here.

2. Know Your Islands

Each of the four main islands in the USVI has its own distinct personality that appeals to some folks and not to others. Not just terrain and conveniences but history and architecture also contribute to the flavor of these islands. Understanding the differences between St. Thomas, St. John, St. Croix, and Water Island will help to make sure that you choose the island that suits you best.  

3. Consider Location and Style of Lodgings

After deciding what island to vacation on, the next step is knowing where on the island to stay and what style of accommodations options exist. There are many options and combinations for style of lodging and location.

Do you want to be on the beach?

In the jungle?

High elevation?

In the city?

In a neighborhood?

Your choices for style of lodging are varied.




*Vacation rentals by owners


*Guest houses


Not sure what’s available or what neighborhood would be best? Read our awesome  St. John Vacation Rentals: Your Ultimate Guide and St. Thomas Vacation Rentals: Your Ultimate Guide.

4. Deciding Upon Comforts and Conveniences.

(Warning: Don’t skip this step. It’s the fun part!)

Now that you know where you want to stay and what time of accommodation you want to stay in, begin making a list of what you need to be comfortable and happy on your VI vacation. If there is more than one of you to consider (maybe your dog or mother-in-law) think of what they need to be happy as well.  Think of everything you could possibly need.

Do you want a kitchen? Kitchenette?

How important is privacy?

Do you need accommodation that can cater to large groups?

How important is convenience?

How important is price?

How important is the view?

Do you want to be within walking distance of places to eat and drink?

Do you need entertainment and activities near by?

Do you need a pool where you’re staying?

If you do need a pool, are you willing to share it with other travelers staying in the same place or do you want a private one where you can skinny dip?

Seriously, how important amenities are to you will determine how much you are willing to pay for them and that depends in large part on how much time you plan on spending there. Get some ideas by taking a stroll through our accommodations listings to see the wide range of options available on each island.

5. Prioritize Your Needs and Wants for Your Budget 

Take the list you created in step 4 and assign a value from 1-5  to each of the items you listed.

5 = can’t live without, 1 = would be nice but not necessary, with 2,3,4 falling somewhere in between. This next step will help you zone in on the perfect balance of needs, wants and budget. If these aren’t realistically aligned you will need to adjust your expectations, like giving up the helicopter pad in favor of the tent platform.

VI vacation rental
Property: Humming Bird
*Ball Park Budget for Vacation Rentals in the Virgin Islands

Time of year, location, type of accommodations and amenities are all important considerations in estimating price. For ball park purposes only, based on 2 people visiting in high season, you can expect to pay on average between $250-$500/night for accommodations. Low season can be about 20% less.  Some privately owned places will negotiate for longer stays but you are more likely to find flexibility if you book during off season or shoulder season and for multiple weeks.  (BTW – A really great idea for families).

6. Book It Baby!

While no rental is perfect, armed with this knowledge and a few insider questions to ask your booking agent, you can avoid some unpleasant surprises. Learn all about the different types of accommodations available in the VI on our St. John Vacation Rentals: Your Ultimate Guide and St. Thomas Vacation Rentals: Your Ultimate Guide. Or, take a stroll through our accommodations listings  and see what we have here.

Review these info pages and links and feel confident enough to book your VI vacation rental. You will be forever appreciated and admired by your family and friends for finding that perfect spot. And…

If you’re feeling uncertain, contact us maybe we can help or even get you a good deal.

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