Why (And How) to Take a Caribbean Villa Vacation

caribbean villa vacation barbados dreamVilla "The Dream" in Barbados.
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By Alexander Britell

While a villa vacation is one of the most fascinating and rewarding travel experiences in the Caribbean, the process of actually finding a villa and embarking on the trip can be daunting. Often, large home-sharing platforms mean a difficult-to-navigate sea of listings, seldom with actual humans behind them.

And then there are companies that do all the work for you. You tell them what you’re looking for and what you want, and they find it; they’ll secure the villa, negotiate on your behalf, provide a buffer between you and the owner if something goes wrong, a full-service travel agency for your villa getaway.

Regardless of how you choose to search for your Caribbean villa, it’s important to know what you’re getting into, which destinations offer the best villa experience and the major questions to ask and think about, staring with the most important one: why should you choose a Caribbean villa vacation.

To learn more, Caribbean Journal talked to Stiles Bennet, president of WIMCO, one of the Caribbean’s leading villa rental specialists.

If you are vacationing with 3 or more people, renting a villa offers you more space, privacy and value vs renting multiple hotel rooms. You get your own private pool, lots of space to spread out and relax, and common living room and dining room areas to share for conversation and meals. If you rent a villa through a full-service agency, you will also have access to a hotel-like concierge service desk and team to take care of special requests and to reserve local activities…so it’s the best of both worlds.

What are the most important things to know about the villa experience?

A well maintained villa in most cases will have the types of modern conveniences you are accustomed to in your own primary residence (wi-fi, Netflix, coffee makers etc), plus frequent house keeping service to keep things tidy during your vacation.

Villas come in all shapes and sizes, so its important to ask questions about a villa’s location, how big a plot of land its on, how close the neighboring houses, what features are included  etc.

Many larger private villas will offer proportional pricing options so you don’t have to pay for the bedrooms your group is not using. For example, if you are a party of five, needing three bedrooms, you can rent a spacious five bedroom villa, and only pay for three bedrooms. The villa rental agency will simply lock the bedrooms not being used, and you get the benefit of staying in a larger home. You aren’t sharing the villa with anyone – it’s just a smart way to get access to more space and amenities. Ask your villa rental agency about this option.

What makes a villa vacation unique?

What’s so great about vacationing in a private villa is how flexible things are. You can decide to be totally self sufficient, or take advantage of the local concierge services team to be treated like royalty – its up to you. A lot of renters enjoy preparing their own meals most nights, so having access to a well accessorized kitchen while on vacation makes that possible. Others like to be pampered, so arranging to have a private chef come in to prepare one or more meals is a real treat. Another bonus of villa life is the ease at which you and your traveling party can come together for socializing and meals, and then seek out your own private spaces for reading and relaxing. It’s hard to match that if your group is spread out across multiple hotel rooms.

Which destinations are preferable for a villa vacation?

Where one chooses to vacation really depends on the experiences they want to have. Travelers who seek good value may find the VI and Grand Cayman to be a good fit. Those who seek a scene with a more active nightlife may prefer the Turks and Caicos or St Martin. Foodies gravitate to St Barth and Anguilla.

If your group is celebrating a special occasion and bringing together a lot of people, you may want to rent a cluster of adjacent villas within a resort like Oil Nut Bay, Amanyara, or Tryall, or to really vacation in style, ask about renting villas on a private resort island like Parrot Cay, Guana Island in the BVI, Jumby Bay in Antigua or Necker Island.

caribbean villa vacation st barth

The two-bedroom Villa Atalante is a great example of a villa ideal for a couple.

What do I need to bring?

The less the better! It all depends on the experiences you want to have. Your rental agency can advise you in advance on everything there is to do in and around the villa you are staying in, which is helpful when deciding what gear to pack. Those interested in playing tennis, golf or scuba/snorkel can ship their gear over in advance, or rent it locally. What you won’t need to bring is gear for the house – it will be well accessorized.

What about the food situation?

A professionally managed villa will have a well accessorized kitchen, including some non-perishable staples like salt, pepper, olive oil etc. You can purchase food and beverages at local grocery stores, and many vacationers find that shopping locally is a fun part of the experience. There is also the option of sending the villa rental agency a shopping list, and having those items pre-stocked in the villa before you arrive. Some agencies have designed a “first night supplies” package of foods and beverages to cover the first 24 hours in the villa so you don’t have to run out and get supplies when you arrive. For either of these options, a small delivery fee is usually applied to the grocery bill, and it’s worth it!

caribbean villa vacation jumby

There is a vast range of villa options across the region, including villas in private-island resorts like Jumby Bay, above.

Do we get daily maid services?

All villas that are professionally represented by an agency will offer house keeping services from two to seven days a week, the frequency varies by destination, and sometimes by villa. Ask your villa rental agency about this. Extra house keeping service can always be arranged on request.

Is there staff?

Each villa is cared for by a villa manager, who is in charge of scheduling house keeping services as well as standard maintenance services like pool cleaning, landscaping etc. A selection of larger villas have the services of a private chef included in the price. In most destinations the staff serving the villa do not live on the grounds, however, there are select larger villas in a few destinations where some of the staff may live in separate cottages on the property.

caribbean villa vacation anguilla

Villa Paradise in Anguilla.

What about safety and security?

Private villas are set up much as your primary residence is, with doors and windows that lock, and in some cases with security systems. That said, most villas are located in very safe destinations.

What services will the villa rental agency take care of?

Villa rental agencies come in all shapes and sizes, offering different levels of services, so it’s worth researching what services an agency does offer before renting from them. Agencies operating on the low end of the service spectrum will reserve the villa you request, give you directions to the villa, make sure it is open and clean when you arrive, and then you’ll never see them. Villa rental agencies operating at the high-end of the service spectrum will provide a consultative service to find the villa that best fits your needs, then will assist with international and local flights, airport arrivals service, rental cars, pre-stocking the villa with groceries, suggesting local activities then reserving them, setting up babysitters, providing 24/7 concierge service during the vacation and more. Often these concierge travel services are provided at no extra cost, so it’s worth seeking out a full-service agency.

Are there concierge services available during my vacation?

The level of concierge service that you get before and during your villa vacation will depend on the villa rental agency that you use to make your reservation. Some agencies do not provide any local services but will leave a local services guide in the villa as a reference. A full-service agency will provide a range of travel services prior to arrival, then will offer a concierge desk and local staff who are available to you during your vacation. It’s worth asking your villa rental agency about the services they provide before you make a reservation with them.

What makes WIMCO unique as a villa rental agency?

We have been in business for over 35 years, and pioneered the full-travel services villa rental agency model. Its reservations department is staffed with a well traveled team of agents who have visited the destinations, inspected villas, dined at local restaurants, and thus can provide a valuable consultative service finding you the villa that best fits your unique needs. Once you select a villa, our concierge department takes over, assisting with international and local flights, airport arrivals service, pre-stocking the villa with food, and arranging any local activities or experiences a client is interested in. During your vacation, our concierge team is only a phone call or text away, ready to answer questions about and reserve anything a client desires. If there is a problem with the villa, or with something while you are in the destination (like a fender bender), we acts as a trusted advisor to sort things out. You are in good hands.

WIMCO’s global portfolio of private villas with concierge service includes properties on eleven Caribbean destinations (including St Barth, Turks and Caicos, Grand Cayman and Anguilla), along with a dozen private island resorts in the Caribbean.

For more, visit WIMCO.