PALM SPRINGS,  CALIFORNIA
Frank Sinatra slept here, at the Twin Palms estate. He also threw parties here that were attended by the biggest stars of the day, and he had at least one memorable row with then-wife Ava Gardner. The story goes that she arrived from Hollywood unannounced, expecting to catch Sinatra with Lana Turner. He reacted by tossing her possessions out of the house and onto the driveway. There’s still a chip in a sink in one of the bathrooms, said to be left by a bottle that Sinatra threw while in a rage.

A quintessential example of mid-century modern architecture, the home was built in 1947 for Sinatra and his first wife, Nancy Barbato. It’s located in the Palm Springs Movie Colony neighborhood, around the block from homes once owned by Al Jolson, Jack Benny, and Cary Grant.

The house, which has four bedrooms, each with an en suite bathroom, features 1950s-era furnishings, a collection of Sinatra memorabilia, a piano-shaped swimming pool, and proximity to the area’s many golf courses.

MAUI, HAWAII
It’s tough to say which is a better way to while away the hours: lounging on the quarter-mile, white-sand beach that abuts the Jewel of Maui estate or lounging at the property’s 60-foot-long infinity-edge pool, which overlooks that beach. For more active recreation, you can take a five-minute walk and play 18 holes at either the Bay Course or the Plantation Course at Kapalua Resort.

The home, which includes five bedrooms and sleeps as many as 12 guests, also features three beachfront hot tubs that together can accommodate as many as 25 people, a media room with a 9-foot projection screen, a recreation room with a billiard table, and a gym with an ocean view.

PUNTA MITA, MEXICO
Casa Papelillos addresses any security concerns its guests might have about traveling to Mexico. The nine-bedroom property is located in Punta Mita, a gated peninsula located about 10 miles north of Puerto Vallarta, on Mexico’s Pacific coast. The estate is located on the beach in the Ranchos Estates neighborhood, which has a beach patrol, two guard-monitored entrances, and 24-hour-a-day security monitoring of the entire neighborhood. Casa Papelillos itself is accessed through electronically operated gates.

Guests also don’t have to worry about the weather. The average high temperature in the summer is 85 degrees, and in the winter it’s 75 degrees.

The three-acre estate contains a main residence and a guesthouse, which together provide more than 19,000 square feet of indoor living space and sleep as many as 18 adults.

Casa Papelillos employs a full-time staff of 10, which includes a chef, waitstaff, and a property manager who lives on-site. Nannies, a massage therapist, a yoga instructor, a manicurist, a surf instructor, snorkeling and dive instructors, and tour guides are available for hire.

 The property’s features include three infinity-edge swimming pools (each overlooking Banderas Bay), a covered dining pavilion that seats as many as 20 people and overlooks the bay, a media room with a 72-inch high-definition television, a fitness room, and rooftop lounging areas atop both the main house and the guesthouse.

LUPITA  ISLAND, TANZANIA
Lupita is a 100-acre landmass in Lake Tanganyika, Africa’s second-largest lake.
You can enjoy kayaking, canoeing, and sunset cruises on the lake and snorkeling in its clear waters. Through October, the weather tends to be sunny and balmy during the day and cool at night.

Lupita is just a 15-minute boat ride from the village of Kipili, which has an airstrip that services chartered flights from Kilimanjaro international airport. You also can charter a helicopter directly from the airport to the island.

Island guests stay in 13 thatched-roof, one- or two-bedroom villas, each of which has only three walls; the missing wall, if it were in place, would block the view of and the breezes from the lake. The one-bedroom villas cover 1,800 square feet, and the two-bedroom
ones are 2,800 square feet.

On the deck of each villa are a stone bathtub and a plunge pool.

LAKE KORA, ADIRONDACK PARK, NEW YORK
You can vacation this fall the way the Rockefellers and Astors used to, at one of the Adirondacks’ great camps in upstate New York. Lake Kora, originally built at the end of the 19th century for the Woodruff family and once owned by the Vanderbilts, can accommodate nearly two dozen family members and friends in a variety of log lodges clustered by the lake.

The camp is set on 1,000 wooded and secluded acres that are about two hours by car from the airports in Albany, Syracuse, and Utica, N.Y. Except for those in the main lodge, all of the accommodations have their own bathrooms and kitchens.

The boathouse, which also includes overnight accommodations, contains canoes, small sailboats, rowboats, a pedal boat, and fishing equipment for guests to use. The camp has a softball field (where long ago the New York Yankees played some spring training games), a lighted tennis court, a billiard table, a squash court, and a two-lane bowling alley.

LOMBARDY,  ITALY
The various celebrities who have acquired villas on Lake Como in recent years—Clooney, Madonna, Stallone—weren’t exactly setting a trend. The wealthy and aristocratic have been vacationing here since the days of the Roman Empire. They, too, were drawn by the beautiful scenery and year-round mild weather.

Built in the 1700s, Villa Mosaico is one of the region’s oldest estates. Among its most impressive features are its five-level garden—which grows roses and other flowers as well as lemon, olive, and orange trees—and its swimming terrace, which, in addition to a pool, also has lemon and olive trees and a stunning view of Lake Como. The property also includes a 200-year-old greenhouse and 11 working fountains.

The estate’s stone dock is planted with roses, creeping jasmine, and oleander, and it accommodates a 32-foot mahogany boat and a 19-foot runabout. Guests of the villa can rent either craft.

The villa, which sleeps as many as 22 people, includes eight master bedrooms. All of them are furnished and decorated with antiques, and some of the bathrooms have antique French or English trough bathtubs.

A highlight of the residence is the music room, which has a 30-foot ceiling, spectacular views of the lake, and a restored antique Blüthner piano. The home also features a billiard room with a hand-carved English snooker table, a media room with a 72-inch TV, and a fitness room.

CABO SAN LUCAS, MEXICO
The summer might be winding down north of the Mexican border, but not in Cabo San Lucas, at the southern tip of the Baja California peninsula. Here, the average temperatures remain in the 80s through November, allowing visitors to continue enjoying the region’s many golf courses, white-sand beaches, and scuba sites. The area is served by an international airport and by a small airfield that can accommodate private aircraft.

Villa Penasco, located in the gated community of Pedrigal, sits on a cliff overlooking Land’s End, a landmark rock formation in the Sea of Cortés. The home includes five bedrooms, each with its own marble bathroom, private terrace, and spectacular views of the Pacific Ocean. The home’s other features include a heated pool and a hot tub on the main terrace, which overlooks the ocean, and a fitness room.

With a dining room that sits as many as 16 people and a media room equipped with a snack and coffee station and a video projector and screen (as well as a 52-inch television), Villa Penasco is well suited to host a small company retreat as well as an extended family.

HEALDSBURG, CALIFORNIA
September is harvest time in and around Healdsburg, which is located about 65 miles north of the Golden Gate Bridge, in the heart of California wine country. The town is surrounded by some of the area’s top wine appellations—Russian River Valley, Dry Creek Valley, Alexander Valley, and Chalk Hill—and is centrally located near more than 100 wineries and tasting rooms. The downtown plaza offers a number of wine-tasting rooms, fine-dining restaurants, upscale boutiques, and art galleries.

Healdsburg Creekside Vineyard Estate lies three miles outside town, in Dry Creek Valley, home to such wineries as Rafanelli, Dry Creek Vineyard, and Ferrari-Carano. Dozens of other wineries are just a short drive from the property. The Dry Creek Store, which carries local wines and microbrew beers, is within walking distance of the property.

The main residence includes a large master bedroom with a reading area, and there are two other bedrooms that are detached from the house. The house and the two bedrooms form an L around an outdoor pool and hot tub (average high temperatures remain in the upper 70s through October). Just beyond the pool are the cool waters and soothing sounds of Dry Creek.