Get More for Your Vacation-Home Dollar

Chris Poore rented in Southampton, N.Y., every summer for six years, but was frustrated by the area’s sky-high purchase prices. After widening his search, he and his fiancé ended up with a white-shingled Colonial in Bellport, a town about 30 miles west—and considerably less expensive. At $1.5 million, the 1.2-acre property cost about half as much as Southampton Village homes they’d seen on much smaller lots.

Home prices in America’s best-known second-home markets have skyrocketed over the past 10 years. Nationally, the median vacation home price in 2015 was $192,000, up 28% from 2014, according to data from the National Association of Realtors. The cost to buy in areas like New York’s Hamptons is particularly steep: There are now over 10 homes there asking $40 million or more.


To escape eye-popping prices, some second-home buyers are turning to alternatives where their dollar can go much further. To be sure, these areas are “lower-priced” only in contrast to their ultraluxury counterparts. And in some cases, these properties may experience less price appreciation over time than those in better-known vacation destinations. Still, there can be many advantages to venturing farther afield. Below, four markets where buyers can find luxury homes at less-than-stratospheric prices.

Instead of the Hamptons… Try Bellport

“You used to be able to get a cute little farmhouse for not that much money,” said New York City real-estate agent Jared Seligman of the Hamptons, the well-known string of Long Island beachfront towns that are popular weekend destinations for wealthy New Yorkers. Nowadays, “it’s hard to find [something that isn’t] a shack for under $2 million.”

Enter Bellport, a village on Long Island’s Great South Bay about 1½-hours drive outside the city. Its denizens include publishing magnate S.I. Newhouse, actress Isabella Rossellini and television host Charlie Rose, according to local agents.

Many weekenders are drawn to Bellport Village‘s charming 19th-century homes, said Annie Rohrmeier of Eileen Green Realty. And in addition to its bay frontage, the village also has an ocean beach: It is a 10-minute ferry ride to a Bellport residents-only section of Fire Island National Seashore, with a wide sandy beach similar to those in the Hamptons.

While there is summer theater, golf and tennis, the village’s tiny downtown has few nightlife and dining options (its weekenders said they prefer the low-key atmosphere).

The median sale price for a luxury Bellport home, defined as the highest-priced 10% of all homes in the market, in 2015 was $746,050, up 12% from 2005, according to Realtor.com. That appreciation is comparable to East Hampton, where the median sale price for a luxury home in 2015 was $2.3 million, up from 15% from 2005.

Instead of Aspen… Try Sun Valley

With its world-class skiing and mountainous natural beauty, Idaho’s Sun Valley has long attracted celebrities like Bruce Willis, and plays host to the annual Allen Co. conference that draws media and tech moguls. But partly due to its remote location in the narrow Wood River Valley, hours from a major airport, the area remains far less developed—and less expensive—than other luxury Western ski enclaves like Aspen, Colo., or Jackson Hole, Wyo.

“You can really get a good value up there if you know what you’re doing,” said Claudia Graham, a Los Angeles-based biomedical company executive who recently paid $1.8 million for a three-bedroom log cabin on over an acre in Ketchum, where most of Sun Valley’s restaurants and nightlife are located. Last winter, Minneapolis resident Ranee Jacobus and her husband Randy, together with Mr. Jacobus’s business partner, bought an 85-acre property in nearby Hailey for $3.85 million. The property contains a roughly 7,300-square-foot log frame house and a guesthouse, both with mountain views.

Prices in the Sun Valley area (which generally refers to Sun Valley resort and surrounding towns) are a half to a third of those in Aspen, according to real-estate agent Sue Engelmann of Sun Valley Sotheby’s International Realty. The catch: getting there. Flights to Hailey’s tiny airport face challenges landing in bad weather, diverting travelers to Boise or Twin Falls, where they are bused two or three hours to Sun Valley. And there are no non-stop flights to Hailey from major hubs like New York City, Boston or Chicago, although the airport has recently added non-stop flights from San Francisco and Denver.

Sun Valley’s market hasn’t yet recovered from the real-estate downturn; two devastating wildfires in recent years also kept prices in check. In Ketchum, the 2015 median for a luxury home was $1.5 million, a 25% decline from 2005, according to Realtor.com. In contrast, the median sales price of a luxury home in Aspen rose 29% to $4.38 million in 2015, compared to a decade earlier.

George and Silvia Serrano’s home near Sarasota, which they bought in 2007. Last year, they bought a nearby 1/2-acre parcel of land for $235,000 and are in the process building a new home on it.

Sarasota once drew its snow birds primarily from the midwest, but more northeasterners have discovered the area. Mr. Serrano raised his family in Connecticut, and had retired to New Hampshire’s Lake Winnipesaukee when he started looking for a winter home in Florida. “In Connecticut, New Jersey and New York, when you say Florida they think of West Palm,” he said, but he found many parts of the east coast to be too crowded, with “too much noise and traffic.”

Since the Serranos moved to the Sarasota area, their children and grandchildren have also moved there.

George and Silvia Serrano with their dog, Mozart. Mr. Serrano, a classical music lover, said he was drawn to Sarasota in part because of its arts offerings, such as the Sarasota Opera and the Sarasota Orchestra.

Fashion designer Sigrid Olsen relocated to Sarasota from New York City in 2011, although she still has a summer home in Gloucester, Mass.

Ms. Olsen’s home on Siesta Key has three bedrooms. She said she chose Sarasota because she wanted a city that was sophisticated enough to appreciate the art gallery and clothing store she planned to open, and she preferred Florida’s west coast because it offers “more undisturbed nature” than the east coast.

Ms. Olsen’s design studio and home office.

Ms. Olsen doing yoga on her deck overlooking a canal.

The swimming pool at Ms. Olsen’s home.

Ms. Olsen said she can bike to the beach in five minutes from her home. “I always had a craving for that barefoot lifestyle,” she said.

The beach on Siesta Key.

Sarasota’s Asolo Repertory Theatre.

Sarasota buyers said they’re drawn to the area by the beaches, walkable downtown and restaurant scene.

In Napa Valley, Gus Kalaris paid about $2.5 million for his roughly 13-acre Calistoga home when he bought it three years ago with help from Will Densberger of Pacific Union.

Mr. Kalaris lives primarily in Maryland but spends time each summer in Napa with his family.

Mr. Kalaris is a winemaker whose labels include Axios and Worthy. His property includes about 11 acres of vines.

Chris Poore and Eyal Dagan’s new home in Bellport, N.Y. Weekenders are drawn to Bellport Village in part for its charming 19th-century and early 20th-century homes, many of them white with green shutters, agents said.

Mr. Poore rented in Southampton in the past, but widened his search when it came time to buy a second home.

The couple plan to start renovating the house this fall.

Mr. Poore, right, and Mr. Dagan, his fiancé. The couple lives primarily in New York City, and Mr. Poore said they love Bellport’s quiet, family-friendly atmosphere, in contrast to “the craziness in the city.”

The Sun Valley home of Ranee Jacobus. The Hailey property, which sits on 85 acres, had been on the market for several years and received several price cuts before she and her husband bought it with a business partner for $3.85 million. They renovated the property and plan to rent it when they’re not there.


Instead of Palm Beach… Try Sarasota, Fla.

Florida’s west coast has traditionally been less expensive than the east coast, where Palm Beach and Miami boast some of the world’s most expensive real estate, said Rick Moeser of Christie’s International Real Estate. And while Naples has grown nearly as expensive as its east coast counterparts, there are still deals about 115 miles to the north in Sarasota, where waterfront homes go “for a fraction of the cost,” he said.

“This part of the country has offered far more value than would have been available on the east coast,” said George Serrano, who paid about $1.5 million in 2007 for his roughly 5,700-square-foot home with a swimming pool in the Sarasota suburb of Lakewood Ranch.

Before buying a home, Brian Clayton said he and his wife explored much of Florida’s coastline. In Naples, he recalled a half-acre piece of land with about 100 feet of waterfront selling for $15 million. In contrast, he paid $4 million for a home with about 200 feet of waterfront on the Sarasota barrier island of Siesta Key.

Fashion designer Sigrid Olsen also recently moved to a three-bedroom rental on Siesta Key, where she said she can bike to the beach in five minutes and do yoga on her deck overlooking a canal. Ms. Olsen, who also owns a summer home in Gloucester, Mass., said she plans to buy a home in Sarasota sometime in the next few years.

Mr. Clayton’s real-estate agent, Kim Ogilvie of Michael Saunders Company, said one of Sarasota’s highest-priced listings is asking $18 million for three houses on nearly 4 acres with about 500 feet of waterfront on the Gulf of Mexico.

Sarasota buyers said they’re drawn to the city’s walkable downtown, restaurant scene and arts offerings. With its laid-back, outdoorsy vibe, however, Sarasota lacks the high-octane social scene of Florida’s east coast, as well as its super-yacht culture. Another reason for its relative affordability is the area’s multiple barrier islands, which allow for an abundance of waterfront homes, according to Jim Soda of Premier Sotheby’s International Realty.

Number crunchers take note: Prices in Sarasota took a tumble during the real-estate downturn of the mid-2000s and still haven’t totally recovered. The median sales price for a luxury property in the Sarasota area in 2015 was $652,508, down 3% from 2005, according to Realtor.com. In contrast, the median sale price for a luxury home in Palm Beach was $3.15 million, up 19% from 2005.



Instead of Lake Tahoe… Try Wine Country

Full of world-class wineries and big-name restaurants, northern California’s Napa Valley region isn’t exactly an off-the-beaten-path destination. But Napa has yet to see the kind of big-ticket sale prices that are now commonplace in other luxury second-home markets.

When the roughly 650-acre Napa estate of the late comedian Robin Williams sold earlier this year for $18.1 million, it was one of the highest prices ever paid for a non-winery Napa property. By contrast, a home on about 3 acres on Lake Tahoe—another popular vacation destination for Bay Area residents—sold in January for $25.25 million.

Despite its name recognition, Napa, as well as the nearby Sonoma Valley, represents a very large geographic area that remains sparsely populated and largely zoned for agriculture. Plus, there is no beach, limiting the pool of potential purchasers. “Our market in Napa Valley is a much smaller market than most people realize,” said Cyd Greer of Coldwell Banker Brokers of the Valley. “It’s a very small buyer pool.”

After bottoming out in 2010, home prices have been on the rise: The median sale price of a luxury home in the St. Helena/Yountville area in 2015 was $1.86 million, up 64% since 2010, according to Realtor.com.

Gus Kalaris paid about $2.5 million for his roughly 13-acre Calistoga home when he bought it three years ago. Mr. Kalaris, a 57-year-old winemaker and distributor, lives primarily in Maryland and has a vacation home in Delaware, but spends several weeks each summer at the Napa home with his family.

He said he was drawn to the property in part because of the views of Mount Saint Helena. Since buying it he’s renovated the two-bedroom house, which has a wraparound porch and a swimming pool, and made some improvements to the vineyards on the property. “I feel like I got the deal of the century,” he said.

Write to Candace Taylor at Candace.Taylor@wsj.com