Imagine you've just arrived in the Caribbean. You're surrounded by hibiscus, lantana and birds-of-paradise as golden morning sunlight pours over you. Long stretches of pristine beach in the distance border sapphire seas dotted with the crisp white sails of boats.

But instead of slipping into the cooling ocean, you find yourself covered to the elbows in axle grease with sweat pouring down your back and limbs aching from trying to change a tire on your rental car with a rickety jack.

That's the position we found ourselves in on the second day of our nine-day trip to Antigua last fall. We were sorely regretting that the wholesale company that had rented us our villa, which didn't have a representative on the island, had also made our car reservation.

After we finally got a painfully skinny spare tire onto our beat-up sedan, we crossed our fingers and prepared to cover two miles of the worst road we had ever seen between our rental villa and the highway. The potholes were big enough to swallow a small marching band.

The website of our villa rental company said it would inform clients if a four-wheel-drive vehicle was necessary on any of the islands that they serve. It didn't even offer us the option. So we found ourselves driving across the island to pick up an SUV on our own dime.

Hours later, we returned safely to our villa in a sturdy Kia Sorrento, but we were out $470. We learned a lesson about renting a villa in the Caribbean: If you're searching online for a rental villa, look for the local companies that specialize in each island. They know the homes they rent and have a customer service representative on hand. Avoid the websites of wholesale companies, which simply consolidate listings. They can leave you twisting in the wind -- and, granted, it's a pleasant wind tinged with sea salt, but you're still twisting helplessly.

You can also find rental villas on such websites as or, where the villas' owners will rent you their home directly -- and thus can be held responsible if they don't deliver what's expected. Here are five Caribbean islands with an abundance of nice vacation rentals: 



TO DO Besides its stunning beaches, Antigua has a slice of rain forest to visit along with a limestone arch carved out by pounding surf called Devil's Bridge, plus Nelson's Dockyard, the world's only Georgian-era dockyard still in use.

RENTAL SCENE The island has only a few homes on its prime white-sand beaches, largely because such real estate is better suited for hotels and resorts, says Eva Heinfling, owner of Blue Escapes Antigua ( Those looking to rent a villa should instead look for homes on a wild beach (meaning the sand has not been cleared of seaweed) or in the hills, where trade winds keep almost all the villas fresh and cool, she says.

We rented two bedrooms in the Dieppe Bay House (a five-bedroom Mediterranean villa, dieppebay in late November for $500 a night. The staff included an amiable maid, a gardener and a pool caretaker. Because it was still the low season (May-November in Antigua) and the home is on a wild beach, we were able to rent at a discount. 



TO DO One of the southernmost of the Caribbean islands, Aruba has reasonably priced direct flights from New York and offers some of the best rental prices for villas in the Caribbean. The island has a mixed ethnic population with an official language called Papiamento. Aruba also offers some of the most vibrant nightlife in the Caribbean, including a party bus, lively restaurants and casinos. Besides its picturesque beaches, Aruba has Tierra del Sol, an 18-hole golf course near the old-stone California lighthouse, which has unparalleled views. For hikers, a visit to a largely undeveloped region in the Arikok National Park is a must.


RENTAL SCENE Attractive villas, depending on their location, can rent for $140 to $215 a night for two bedrooms, says Gemma Wilson-Teeken, the vacation rental coordinator for Aruba Happy Rentals ( Most are located in the Noord, or north, section of Aruba, where resorts are concentrated and long stretches of beach with powdery sand are found.

A bit pricier than average is Casa Juliana, a three-bedroom home with a swimming pool that costs $242 a night for six people in Aruba's low season (April 15-Dec. 15). The rental price includes an allowance for electricity, which is expensive on Aruba, Wilson-Teeken explains. 



TO DO Raw beauty abounds: The 27-by-14-mile island has two lush tropical peaks called the Pitons and some of the best snorkeling in the Caribbean. St. Lucia is also noted for its 19,000 acres of dense tropical rain forest, where exotic birds and rare plants abound. 

RENTAL SCENE Oasis Marigot Hotel & Villas is a family-run rental business with about 20 properties available -- competition is "very strong" says owner Jacques Binette, so the company offers discounts or free night offers even in the high season (

Oasis Marigot offers the first floor of a villa called the Great House, which has one bedroom and a swimming pool, along with an attached structure with one bedroom called The Cottage, for $1,295 a week (working out to $185 a night) for two couples from April 16 to May 31. St. Lucia's high season runs from December through April, and the months of May and June are popular with honeymooners, Mr. Binette said. Currently, the Great House is $229 a night. 



TO DO While Antigua is still rough about the edges, St. Barth has a level of sophistication that's perhaps reflective of its French heritage. An island with natural beauty, it tends to attract the rich and glamorous, including celebrities. St. Barth is just 8 square miles but is replete with coves, called anses, in which visitors can sun themselves in rocky-bordered privacy. It's also notable for its high-end shopping and fine restaurants. 

RENTAL SCENE Prices for ├╝ber-luxurious rental villas tend to be higher than other Caribbean islands. For instance, the Villa au Soleil, a four-bedroom home rented by St. Barth Properties ( and owned by comedian Steve Martin, costs about $1,153 a night for two couples using two bedrooms. The villa is part of the company's Grand Cru collection, which means it offers hotel services such as continental breakfast and turndown service. Good to know: the company inspects its villas twice a year to ensure they're up to snuff, says founder-president Peg Walsh.



TO DO St. John is one of the more accommodating and familiar Caribbean islands for Americans. Almost three-quarters of St. John is preserved as a national park, with thick and dry forest and lots of hiking trails -- but that also means most of the stunning beaches featured on its postcards are also protected from development. Tourists can also hop a ferry to St. Thomas, which is one of the Caribbean's important centers for sailing, or to St. Croix, which has interesting Danish-style buildings and excellent shopping. 

RENTAL SCENE Villas in St. John tend to have architecture reflecting the West Indian style, with large arched windows and shower rooms that open up to gardens, says Laura Brego, owner of Destination St. John Villa Rentals ( Like the villas on most of the Caribbean islands, rental homes on St. John come equipped with beach equipment such as towels, coolers -- and often beach toys. They do not, however, have a staff, she says.

While prices can range from $360 to more than $1,430 a night in high season (Dec. 15 to about April 15), renters can expect a 30 to 50 percent dip in the low season, she says. Winsome House, a two-bedroom, two-bath villa designed in the style of a historic plantation home, is $679 a night during the high season for two couples; in the low season it's $371 a night. 


Top tips 

1. AVOID PEAK TIMES Look for a villa in the off-season, which is generally from about May to November in the Caribbean. The holidays, especially Christmas and New Year's Eve, are when villa prices tend to increase.

2. PASS ON GROOMED BEACHES Rent a home that's on a wild beach or in the hills as opposed to an expensive oceanfront villa.

3. RETHINK AMENITIES You will most likely get what you pay for -- provide your agent with your "must haves" but know that many Caribbean homes are not air-conditioned and do not have Internet access.