4 Getaway Destinations that Are Perfect for a Second Home


You’ve just had a bluebird powder day in Jackson Hole, caught the perfect wave in Hanalei Bay, or made a bunch of birdies on the back nine at Bandon Dunes, and it suddenly becomes crystal clear: you need to spend more time here. Even better — you need to own a piece of this paradise. Swept up in the moment and under the spell of vacation, you feel like a second home is a really good idea. But is it?

Maybe, if the pull toward the “home” part is genuine and strong. “Owning a second home is a decision that can largely be based on wanting to become part of the experience in another community,” says Marin County realtor Tracy McLaughlin, who owns a second home in Aspen. “Dropping into hotels or Airbnbs is great short term, but really doesn’t allow you to become connected to people who live there,” she adds. “I also think you can create great traditions that become a fabric of your own family by celebrating year after year in one location.”

The practical advantages of owning of a second home are clear: it’s a potential asset that could appreciate; you can style the property to your taste and drop in any time; you can ditch the heavy luggage and leave your gear there; you can rent or swap it out, host family reunions, make new friends and discover a new locale. Sounds good, right? But there are hard, cold realities to consider too, like unexpected expenses, two mortgages, HOA fees, property tax, maintenance, headaches with renters or unfamiliar property managers, guilt for not using the place enough or feeling obligated to use it rather than travel someplace new.

Many real estate experts believe you should only buy a second home if your first home is paid off or if you have the cash to pay for the new one, so you are not taking out another loan. “Second homes should only be for people who have the wealth to be unconcerned with the expense of owning a second home for the short periods they are going to use it, “says San Francisco developer Rich Singer. “And keep in mind that this expense includes the considerable time and energy involved in owning and maintaining a property as well as just financial cost.”

Some prospective buyers may expect a second home to be an income generator or pay for itself, but “if you are planning on renting it for income,” Singer says, “the amount will very likely be insufficient to make it a good investment versus other pure investment-minded paths.” Moreover, “if you are going to share with complete strangers,” he says, “then why not just flip the table and be a renter yourself and save a lot of time and money?” Plus, “the 2018 tax changes justly got rid of any tax benefits of a second home.”

Even appreciation in value might not be what you’d expect, he warns. “Homes in vacation areas fluctuate in price much more than homes in areas where people generally have their primary residence,” Singer says. “Buying now after so many years of an up cycle puts you at extreme risk of losing your investment.” His advice: “It’s always fun to dream when you’re on vacation, but sober up back at work for a while, paying bills, before you make any long-term second-home commitments you’re very likely to regret.”

Still, second homes are often about intangible value more than anything else. If you look at the purchase only through an economic lens, it likely doesn’t make sense, but if it’s a decision that leads to family bonding and lifelong memories in a new community, that’s another story, as you can’t really put a monetary price on those things.

According to a recent article in the Wall Street Journal, the hottest second-home destination in the U.S. is Palm Springs, California, followed by Nokomis, Florida, and Lake Geneva, Wisconsin. Here are four second-home spots popular with our readers.


An Island Retreat for All Ages

There is luxury and there is casual luxury — a term that perfectly describes Kohanaiki. Founded in 2011 in a partnership with Kennedy Wilson and IHP Capital Partners, the private residential club and development, four miles south of Kona International Airport, is situated along 1.5 miles of Big Island shore. There are numerous amenities exclusively available to member residents and their families and guests.

The centerpiece is the 67,000-square-foot Shay Zak–designed Clubhouse created to maximize views overlooking the golf course and sunsets on the Kona Coast. It houses Konane, an upscale chop house and sushi bar, one of two restaurants on the property. The oceanfront Beach Club is another great choice for meals and provides the unique option of letting guests dine at a table on the sand. Fresh and local ingredients are standard fare with chef Patrick Heymann overseeing both restaurants.

The Clubhouse.
The Clubhouse.

The property has been described as “golf nirvana.” The Rees Jones–designed 18-hole course is perfectly maintained and flows through ancient lava fields with six oceanfront holes on the back nine. Tee times are paced, with no chance of being rushed or having to wait to tee off on any hole. As an added bonus, luxury comfort stations throughout the course have air-conditioned rest rooms and snack areas with complimentary soft drinks, beer, wine, frozen mai tais, soft-serve ice cream, popcorn, cookies, trail mix and more.

Outdoor activities include deep-sea fishing, outrigger canoeing, stand-up paddleboarding, snorkeling, yoga on the beach and swimming in two pools (one for adults and one for families), with towels and equipment provided. Resort members are assigned a golf cart on arrival, so there’s no need to drive a car on property or hassle with parking: attendants promptly park your cart when you pull up to your destination, whether it’s a restaurant or beachside activity venue. Indoor activities include yoga, Pilates, workouts in a state-of-the-art fitness center, bowling in a four-lane alley, movie-watching in a 21-seat theater and a full menu of spa treatments.

Rees Jones–designed 18-hole golf course.
Rees Jones–designed 18-hole golf course.

To become a resident: homes and lots are available from $3 million to $20 million; a Hale Club membership can be purchased at market rate. The Hale Club consists of 17 free- standing completely furnished homes and are available to members for 45 nights a year. It’s an ideal option for those who want to try out the lifestyle before purchasing a home or lot. The Hale Club membership investment will be applied toward any purchase of real estate on the property if executed within two years. There are a limited number of Hale Club memberships available and the membership will gain or lose value relative to market conditions.

Whether Kohanaiki is a primary, second or third home, time spent there can be the ultimate Big Island experience while being both activity-filled and restorative. Residents and members report that the property lives up to its promise to provide casual luxury for all ages.


A Golf and Wine Paradise

If exceptional golf and extraordinary wine sound like a great pairing for a home away from home, Mayacama is your ticket. An easy drive from Healdsburg, the exclusive golf and residential community celebrates wine country with emerald fairways, a regal clubhouse, Tuscan-style architecture, alfresco living, farm-to-table dining and a wine program to impress the most refined oenophile.

Set on 675 acres, the property has 31 home sites and 20-some villas and casitas tucked into the landscape or over- looking the Jack Nicklaus signature course. Following Scottish tradition, the walking course meanders through oak-studded hillsides and golden valleys with elevated tees, undulating greens, water features and natural hazards providing challenges along the way. And while you won’t need a tee time, a caddie can guide you through a meticulously maintained course that’s ranked among the top 100 in America.

Home buyers may gravitate to Mayacama for the golf, but some end up staying for the wine. Mayacama’s 40 Vintner Members, who produce wines with Parker ratings 92 and above, readily share their offerings with the community: their wines are spotlighted at monthly wine dinners — often seven-course seasonal affairs by executive chef Scott Pikey, who pulls from the “bounty of the county” and his own on- site garden and beehives. There’s also an annual All Vintner Pour each May, a chance to try the wines with food stations and music, following that morning’s All Vintner Cup, when you can play with one of the winemakers in a vino “pro- am.” Owners also have access to special wine allocations at good prices and can store up to three cases in their personal locker in the Mayacama wine cave. Cheers to that.

The rotunda at Mayacama.

Being a multigenerational community, Mayacama offers recreation for every age, including bocce ball, biking, hiking, tennis and swimming in an Olympic-size pool. You can bliss out in the European-style spa or burn calories at the fitness center. A creative kids’ program includes themed summer camps, arts and crafts, a trapeze circus camp, animal safaris and science projects. Young golfers can discover their swing and chip shot during junior boot camps. Families enjoy drive-in movies and holiday parties.

If you want to get into the real estate game here, options range from fractional ownership to buying to building a custom home. You can become a Residence Club Member with a one-tenth interest for $400,000 including golf privileges and 28 residence days guaranteed per year, or you can flat-out buy a fully furnished three-bedroom Tuscan villa for $3 million. The villas are maintained and managed by the club, and if you use yours fewer than 120 days a year you pay no property taxes or maintenance. Twenty-one of the property’s 31 single-family home sites have been built out, but some one- to-two acre lots remain available at an aver- age price of $1.2 million. Completed single-family estates occasionally come onto the market in the $4.5 million range.

Another member bonus: a 24/7 concierge staff can stock villas with favorite foods, create itineraries for customized VIP winery tours, and more.


A Luxury Base Camp in the Great Outdoors

For those wanting an alternative to the chaos of traffic- choked Lake Tahoe, Nakoma offers refuge. Head north from Truckee on two-lane Highway 89, and 45 minutes later you’ll find a tranquil wilderness spot with an easy pace, perks and affordable real estate.

The heart of this mountain resort is a 42-room lodge and an architecturally significant clubhouse designed by Frank Lloyd Wright. The 1923 plans were purchased by Nakoma from Wright’s legacy firm Taliesin, and the club- house finally came to life in 2001. Soaring ceilings, stained glass, a 60-foot-tall four-sided fireplace, decorative Native American motifs and friezes reflect Wright’s touch. Picture windows in the octagonal room frame long Sierra views and elicit a sense of grandeur by pulling in the natural wonder- land outside, a trademark aspect of Wright’s organic style.

Dinner at the Frank Lloyd Wright– designed clubhouse at Nakoma.
Dinner at the Frank Lloyd Wright– designed clubhouse at Nakoma.

The Residence Club at Nakoma offers shared ownership in Frank Lloyd Wright–inspired studios and one- and two- bedroom villas designed by Taliesin-trained architects that line the 10th fairway of the Dragon Golf Course, with prices ranging from $49,750 to $89,625, including golf member- ships. For casual single-family living, Ascend at Nakoma offers two-acre lots for an average price of $90,000. Buyers can build a custom home or take the turnkey route and let Ascend’s team (Grouparchitect, Method Homes and Mark Tanner Construction) build them a two- to four-bedroom mountain home with indoor/outdoor living space and stylish Restoration Hardware interiors for about $300 a square foot. That includes architectural planning, engineering and permits. Homeowners are also welcome to put their residences into Nakoma’s rental pool when not using them.

Ascend owners have access to the brand-new center- piece of the community — Altitude Recreation Center, a 12,000-square-foot glass jewel box with floor-to-ceiling windows. Families gather here for year-round swimming in the heated pool, hot tub soaks, tackling the climbing wall, workouts at the fitness center, flicks in the movie theater and healthy fare at the Bar & Bistro. Elsewhere, kids can busy themselves in a game room or crafts center while Mom and Dad play the Dragon Course or relax in the spa. Plans are in the works for pickleball, tennis, volleyball and basketball courts, and an adventure park with a zip line, disc golf and bike park.

The pool at Nakoma
The pool at Nakoma

But the real allure of Nakoma lies in its pristine surroundings, a region deemed the “Lost Sierra,” with more than 20 glacial lakes just 10 minutes away in the Lakes Basin Recreation Area; the nearby Sierra Buttes, reminiscent of the Swiss Alps; and even part of the Pacific Crest Trail. It’s an alpine playground where you can mountain-bike, fish, cross-country ski, snowshoe, horseback-ride, hike, or just unplug and immerse yourself in the beauty of the great outdoors.


A Tropical Adventure Spot

Swaying palm trees, gentle lapping turquoise waters, a white sand beach speckled with palapas — this place has all the trappings of a luxury resort, but even better, it’s your second home. Located half an hour north of the Cancun airport, close enough to the action yet out of the fray, the La Amada residences within the gated community of Playa Mujeres is a secluded playground in one of the most idyllic settings in the region.

The property recently underwent an $8 million renovation by the firms Hamak and PowerPlay Destination, the latter of whose portfolio includes Montage Residences Kapalua Bay on Maui and Kohanaiki on the Big Island. Starting in the mid-$300,000s, the 215 residences range from one to three bedrooms and feature spacious kitchens, marble floors, large sliding doors, private terraces and deep soaking tubs; the penthouses include sprawling accessible rooftops.

La Amada
A private terrace at La Amada.

Among the additions to the property’s already robust offerings are a beach club replete with expansive decks, shaded cabanas, a swim-up bar and two new infinity rooftop pools. Other highlights include a well-appointed gym with views of the pool and gardens and a marketplace cafe that carries grocery staples and to-go offerings.

An 18-hole Greg Norman–designed golf course, considered one of Mexico’s best, is just outside the residences and is surrounded by lush jungle flanking the Caribbean. La Amada’s on-site deepwater marina has 176 slips for boats up to 200 feet in length.

The property is a prime fishing and marine adventure spot, located next to the world’s second-largest coral reef and close to the world-renowned scuba-diving of Cozumel. A quick boat or ferry ride away lies charming Isla Mujeres, where visitors can explore by golf cart and have ceviche, margaritas and affordable massages on the beach.

Anne Wycoff

Ann Wycoff is a travel and lifestyle writer whose work has appeared in San Diego Magazine, Coastal Living, Modern Luxury, and many more. She lives in Encinitas, CA with her husband and daughter, and believes in traveling with a purpose.