Does a tropical island vacation feel a bit like walking the plank?

In winter, better hotels require minimum stays and nonrefundable deposits. After you've locked in a destination, you have to find flights, then hope for a towel-size patch of beach to call your own. These aren't easy tasks as you compete with blizzard-dodging crowds seeking an island escape.

It's enough to make Johnny Depp slather on another layer of mascara.

But you don't have to break the bank or stress out to enjoy the Caribbean's beautiful bounty. How? Head south in summer, the region's low season. Light crowds mean easier planning, and hotels across the region drop rates as much as 40 percent from winter prices. These deals allow you to step up to a level of luxury that may be unaffordable in high season.

Here are five resorts that are summer steals. Peg leg and eye patch are optional.

The Ritz-Carlton, St. Thomas

St. Thomas, in the U.S. Virgin Islands, is famous for cruise ships and shopping, but I like it for the vistas from atop its muscular mountains. The view from the Ritz-Carlton, the island's top hotel, is nearer sea level but no less stirring, and a sublime infinity pool drinks in the panorama of nearby Turquoise Bay.

Photos by DAVID SWANSON/Special Contributor

The infinity pool at the Ritz-Carlton, St. Thomas sits on the edge of Turquoise Bay in the U.S. Virgin Islands.

The 180-room resort completed a $40 million renovation in 2007 that gently updated the Italian Renaissance décor and modernized the rooms, while expanding the spa.

Bougainvillea drapes the peach-colored buildings, and lush gardens separate them. On site are a beautiful beach, tennis courts, health club and dive shop. Four dining options range from poolside to sophisticated. And every morning a Shop Talk class coaches guests on where to find the island's best buys.

Winter rates start at $599 a night, plus 20 percent tax and service. But stay June 15 through Oct. 31, and the rate drops to $269, a 55 percent saving. Plus Ritz-Carlton throws in a $200 credit toward a snorkel or sailing trip on its 53-foot catamaran.

Contact: 1-800-542-8680; www.ritzcarlton.com.

Jamaica Inn, Jamaica

Jamaica is booming, and modern, all-inclusive complexes are plentiful. But the 1950s classic Jamaica Inn has survived and carved a new niche for itself.

The 47-room inn once drew such notables as Errol Flynn, Katharine Hepburn and Winston Churchill. Today's eclectic clientele includes model Kate Moss and singer Tori Amos, who wrote an ode to the hotel. They come for privacy, a child-free environment and low-tech comfort. Guests trade the distraction of a TV for a huge patio or balcony suitable for hours of lounging and croquet on the broad lawn. Peninsulas at each end of a pretty beach keep the riffraff at bay. A spa offers treatments using local plants.

Rates start at $290 April 16 through Dec. 14, tax and service charges included, which represents a 48 percent break on winter's starting rate of $550.

Contact: 1-800-837-4608; www.jamaicainn.com.

Kú, Anguilla

Anguilla has been discovered by high rollers who are on a spree of developing luxe resorts. That's why it's refreshing to have Kú, a classy, 27-suite hotel on one of the Caribbean's finest beaches.

Each 775-square-foot room has white-on-white décor, ultra-plush bedding and extras such as a CD/DVD player and fully equipped kitchen. All have at least a glimpse of the sea.

There's a bar, dive shop, spa and gym. DJ music plays in the restaurant several nights a week; live music, on Sundays. Swaying palms wrap the free-form pool. An adjoining market sells pâté, cheese and wine. And when you want a change of scene, it's a short walk to Shoal Bay's other beach bars.

Summer rates (April 1 to Dec. 19) start at $180 plus 20 percent tax and service, a 43 percent saving from high-season's starting rate of $315.

Contact: 1-800-869-5827; www.ku-anguilla.com.

The Hermitage, Nevis

Richard and Maureen Lupinacci bought a plantation house high on the slopes of Nevis Peak. In transforming it into a small inn, they discovered The Hermitage is no ordinary plantation. The small greathouse is about 340 years old – probably the oldest wooden house in the Caribbean. It predates when Adm. Horatio Nelson lived on the island.

The family-run Hermitage inn on Nevis is several hundred years old and offers relaxation in a pastoral setting.

The 15 rooms they converted or added kept with the original style: wooden, fringed in gingerbread and swathed in bright colors. A small pool was added, and a stable for Mr. Lupinacci's horses. The restaurant serves elegant dinners, and the Lupinaccis often join guests at a communal table for dinner and robust conversation on the veranda.

Although the family-run Hermitage is about relaxation in a pastoral setting, activities include horseback rides, tennis and in-room spa treatments.

Rooms in low season (April 16 through Dec. 15) start at $170 with breakfast plus 19 percent tax and service. It's a 48 percent saving from the high-season rate of $325.

Contact: 1-800-682-4025; www./hermitagenevis.com.

Cooper Island Beach Club,

British Virgin Islands

Most private island resorts – outposts where a single hotel lavishes guests with dreamy seclusion – cost $1,000 or more a night in high season. But 1 ½- by half-mile Cooper Island, a 35-minute ferry ride southeast of Tortola in the British Virgin Islands, usually isn't mentioned among them.

Visitors lounge on the beach at Cooper Island Beach Club in the British Virgin Islands.

You won't find a spa, swimming pool or fancy wine cellar on Cooper Island. What you will find is a generator-powered outpost with six quaint cottages, each containing two units that have rattan furnishings, kitchenette, semi-outdoor shower and porch facing the Sir Francis Drake Channel. Snorkeling from the beach at your doorstep is excellent, plus there's a small dive shop catering to guests. The R.M.S. Rhone, possibly the Caribbean's most revered wreck dive, is a short boat ride west.

You can bring groceries from Tortola, but the hotel restaurant is good and fairly priced, with dinner entrees under $20.

In summer (June 1 through Oct. 21), the price for this seclusion runs $125 a night plus 17 percent tax and service, 43 percent below the winter rate of $220.

Contact: 1-800-542-4624; www.cooper-island.com

David Swanson writes the Affordable Caribbean column for Caribbean Travel & Life magazine.