It’s Becoming a Breeze to Rent Caribbean Villas

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Sometimes a hotel room just isn’t enough. For those in search of parlors and patios to gather a far-flung family or privacy in the form of their own moonlit pool, booking a villa, cottage or condo is the way to go.

“The biggest benefits are more space, more privacy and the convenience of having a kitchen,” says Jon Gray, senior vice president of HomeAway, a vacation rental company. Rentals often come at less cost than booking multiple hotel rooms.

“The average rental is $1,500 a week for a two-bedroom, two-bath property,” Gray says. “The average hotel room is 325 square feet, and the average vacation home is 1,850 square feet.”

Some villas, especially in the Caribbean, come with a butler who can serve you a daiquiri at sunset on your private deck and a cook who dishes up lobster curries for dinner.

But how to choose? Vacation rental marketplaces, such as FlipKey and HomeAway, function like digital bulletin boards, enabling owners and renters to meet. With huge inventories, these companies do not inspect units. The owner-written descriptions may be accurate or inflated. Typically, there’s no on-site management or local team to contact if something goes wrong.

Villa rental companies, such as WIMCO and Villas & Apartments Abroad, may provide concierge services and destination expertise, and they help match properties to clients’ personalities.

Here are some prime companies for vacation home rentals in the Caribbean:


FlipKey offers condos, cabins, houses and villas. Users can book about 40% of the lodgings online, and properties with the best combination of reviews, rates, photos and other factors rise to the top of their lists.

Properties: 240,000 listings in 12,000 destinations, including 15,000 in the Caribbean.

Filters: Search by deals, Internet availability, lodging type, bedrooms, price, pool, child-friendly.

Pros: Large inventory with user reviews. Pay through FlipKey Payments and receive free insurance up to $10,000 if the lodging proves to be significantly different from what’s described or is unavailable.

Cons: Lodgings not inspected. A booking fee may be required. No concierge service.

Sample fee in Jamaica: $400 a night for a three-bedroom, beachfront, staffed villa.


Also owned by HomeAway, it’s a smaller site that focuses on special offers and last-minute deals, which appear at the top of lists.

Properties: 35,000 in 70 countries; concentrated in Florida and the Caribbean.

Filters: Search by deals, last updated, bedrooms.

Pros: Easy to find deals.

Cons: No online booking. Lodgings not inspected. No concierge service.

Sample fee in Jamaica: $208-a-night average for a three-bedroom rental.

Villas & Apartments Abroad

Owner Sylvia Jones has been advising clients on rentals for more than 40 years. She focuses on high-end lodgings, particularly those that can host multigenerational families and VIPs.

Properties: 400+ worldwide; Caribbean is a top destination.

Filters: Search by bedrooms, budget, golf, horseback riding, piano, gym and staff.

Pros: Service and ultra-luxury listings. Showcases some villas that can handle weddings.

Cons: Luxury villas are pricey.

Sample fee in Jamaica: $7,000 for seven nights in a five-bedroom villa in summer, staffed with a cook, butler and maid., 212-213-6435

WIMCO Villas

WIMCO focuses on luxury villas, each of which has been viewed by a staff member. Arranges snorkel outings, boat charters, restaurant reservations and other services.

Properties: 1,200 villas, including 800 in the Caribbean.

Filters: Search by villa name, location, size, date, pool, child-friendly and more.

Pros: User-friendly site; 24/7 concierge service.

Cons: Luxury villas are pricey. Fewer user reviews than on mega-sites.

Sample fee in Jamaica: From $277 per bedroom, per night for a five-bedroom villa that can be rented as a three- or four-bedroom villa. Includes staff., 800-449-1553

HomeAway and VRBO

With 775,000 properties in 171 countries, HomeAway Inc., which includes HomeAway, as well as VRBO and VacationRentals (see below), is the world’s largest online vacation rental marketplace. HomeAway and VRBO (Vacation Rentals by Owner), the older company, post essentially the same inventory, with some exceptions. VRBO has fewer filters to sort material. About 15% of HomeAway and VRBO’s inventory is bookable online. Instead of concierge services, the sites encourage renters to contact owners for local information. Rental insurance is available for a fee.

Properties: 575,000 in 139 countries. About 50% U.S. inventory; other concentrations in the Caribbean, Europe, South America, Asia.

Minimum stay: Varies by owner.

Filters: HomeAway: Search by price, bedrooms, accommodation type(apartment, condo, cabin, castle, villa, etc.), location (mountain, beach, skiing, golf, lake), luxury, budget, air conditioning, pool, child-friendly, wheelchair-accessible. VRBO has fewer options.

Pros: Useful filters narrow the huge inventory. Many user reviews.

Cons: Lodgings not inspected. A listing’s position is determined by the package purchased by the owner. No concierge service. A booking fee may be required in addition to the rental fee.

Sample fee in Jamaica: $176-per-night average for a two-bedroom rental, and $341-a-night average for a three-bedroom rental.;


Villa vacations come with many great bonuses but also some big bewares. Here are some tips to make your time away as sweet as the location.

* Use a reputable site or agency that’s been in business for awhile.

* Decide how much customer service you want. Vacation rental marketplaces don’t match you to a property and don’t arrange outings at the destination, but a villa rental agency will do both.

* Find out if a booking fee for the property you want is required. If an owner has purchased a low-cost posting plan with the vacation rental marketplace, then you may be required to pay the company an additional fee of about 5%-10% of the rental price.

* Get the rental dates, fees and rules in writing before you pay.

* Understand what is and isn’t included in the rental fee. Some properties may not come with sheets, towels or pots and pans, or the owners may charge extra for these items.

* Know the payment schedule and cancellation policy. Typically, a 30% deposit is required to hold a reservation and full payment with no refund is required 60 to 90 days before departure, although these rules vary by owner and by agency.

* Find out whom to contact at your destination in case of a problem, lock-out or an emergency.

* Pay online with a credit card or through a payment service such as PayPal. These provide more protection should something go wrong than does payment by personal check.

* Get suggestions about outings and area restaurants before departure from the owners or from the villa rental agency.

* Discuss how expenses for groceries, car rentals, outings and restaurant meals will be shared by your group. Never assume that everyone plans to share the costs equally and don’t leave home with this gang, even if they are your best friends or family, unless you are comfortable with the financial arrangements.