5 Homes away from Home

Choosing the Perfect Maui Vacation Rental


Story by Marti RosenquistStory by Marti Rosenquist


Vacationing on Maui with family or friends? You could reserve a block of hotel rooms, but then you wouldn’t have the home advantage of a central rally zone, or a kitchen for preparing communal meals. The most meaningful family encounters seem to occur around the hearth and in the galley, so it’s no wonder vacation homes have become so popular for family reunions and other special occasions.

On an island this varied, you’re pretty sure to find the vacation rental that suits the tenor of any group. Most include amenities you likely don’t have at home, such as private beaches or Jacuzzis. And they come with the expertise of professional property managers who ensure that your ‘ohana (family) has a relaxed and happy stay.

Here are five examples we scouted out — lodgings for unwinding, or for serving as home base from which to launch island adventures. Whether it’s an oceanfront luxury estate, a retro beach bungalow, or a hippie-chic hotel, each property offers a distinctive setting where the folks you love can step outside the daily grind, have fun together and build what are sure to become cherished memories.

Wailea vacation rentals

Wailea Sunset Estate

South Shore
Bedrooms: 4
Baths: 5½
» Pampered privacy
» Upscale comfort
» Oceanfront
» Dual family rooms
» Separate honeymoon cottage

Price: From $2,250/night
Contact: (888) 875-2818, ext. 6; Info@TropicalVillaVacations.com

Fitzgerald was wrong. The rich are just like you and me — they long to be completely comfortable, stress free, and cosseted like royalty. And here is the place for it. Low-key pampering (the ultimate luxury) for those who can muster the price.

Three bedrooms occupy the second floor of the main house, including a stunning master suite with private lanai and jaw-dropping ocean views. The two guest bedrooms are accessed via a different staircase off the kitchen. The upper floor’s lanai invites outdoor rendezvous for morning coffee or afternoon drinks.

Built in 2005, Wailea Sunset Estate epitomizes upscale lodging, with twin family rooms at opposite ends of the house, gourmet kitchen, private office space, multiple lanais and a beautiful pool. A separate structure houses the definitive honeymoon suite, complete with sumptuous king bed, mood lighting, and high-tech media center.

Setting the property further apart from other run-of-the-mill multimillion-dollar, oceanfront digs are the stately grounds: an acre of manicured lawn and private ocean frontage. It’s hard to imagine more ideal accommodations for an ‘ohana or group of friends celebrating a special occasion.

Paia vacation rentals


Pa‘ia Inn Hotel

North Shore
Bedrooms: 5 in the inn; multiple options, from studio suites to a private 3-bedroom villa
» Hip décor
» Complimentary high-speed WiFi
» On-site shops
» Courtyard café serving breakfast and drinks
» Private oceanfront access and lawns
» Walk to boutique shops, restaurants, Mana Foods

Price: From $189/night for room at the inn; $999/night for 3-bedroom oceanfront villa
Contact: (808) 579-6000; www.paiainn.com

A cross between a boardwalk hotel on the strand in Hermosa Beach, a B&B in Bali, and the Hotel San Jose in Austin, the Pa‘ia Inn reflects an eclectic personality. The front entrance is directly off the main drag in artsy/touristy Pa‘ia, but the backyard fronting the ocean is a world away from the bustle.

It’s at once a laid-back beach-town hostel and a hip urban retreat sporting high-thread-count sheets, lightning-fast free WiFi, and one of the world’s “sexiest hotel staffs,” says concierge.com. Wander behind the main hotel past the courtyard and café, and you’ll find a surprising collection of structures with a variety of junior suites, one- and two-bedroom mini-abodes, and one of the very best rentals on Maui, the coveted Beach House.

The fully remodeled three-bedroom house offers feng shui-focused living. Completely private with gorgeous furnishings and island-style art, it’s equipped with a gourmet kitchen, open-air living room with giant flat-screen TV, Jacuzzi spa and private garden.

If your group includes more than eight people, don’t fret. Simply book the extra guests or distant cousins in one of five rooms in the inn. Located on the second floor of a former boarding house, the bedrooms radiate off a central living area; each has a private bathroom and luxury touches like fine linens, flat-screen TVs and charming wardrobes and furnishings.

Kaanapali Beach House rental


Sea Shells Beach House

Bedrooms: 3
Baths: 3 full, 2 half
» Lagoon-style heated pool
» Dual laundry centers
» Direct access to sandy beach
» Stocked kitchen
» Covered outdoor kitchenette
» Walk to shopping, restaurants, entertainment

Cost: From $1,850/night
Contact: (888) 875-2818, ext. 6; Info@TropicalVillaVacations.com

If members of your ‘ohana like to be where the action is, Sea Shells Beach House could be an ideal choice. Located behind privacy gates on an acre of land, the single-story home was one of the first built directly on Kahekili Beach (known locally as Airport Beach). A discreet path leads from the hush-hush enclave of the backyard directly to the well-traveled shore. From there you can wander on foot south to Whalers Village and Ka‘anapali resort hotels, with high-energy dining and entertainment options along the route.

The great room of this contemporary residence has cathedral-style beamed ceilings and comfortable furniture that welcomes sinking in, relaxing and enjoying the state-of-the-art media center (sound surround, HDTV, high-speed wireless). Each of Sea Shells’ three bedrooms has its own private en suite bathroom and entertainment system, as well.

The lagoon-style free-form pool is heated for comfort in winter months and lighted by tiki torches at night. There are no posted hours for this pool, so a midnight swim in the warmed waters is a must for Sea Shells houseguests.

The covered outdoor dining area has a gas grill and fridge, plus all you’ll need to serve lunch or dinner al fresco. The indoor kitchen can accommodate multiple cooks and is stocked with the pantry items most often used by vacationers. Then again, you could go all out and hire a personal chef for the week!

Haiku bed and breakfast


The Windward Garden B&B Ha‘iku

Bedrooms: 3 in main house
Bathrooms: 2 in main house
» Hideaway location
» Low EMF, solar powered, certified green
» Chemical- and pesticide-free property
» Enchanting plantation-style house, lawns and garden, romantic getaway cottage
» Across the road from Maya Yoga
» Walk to ocean bluffs

Cost: Suites from $135/night; entire house $400/night, $8,000/month
Contact: (808) 268-3874; www.windwardgardenbandb.com

Since moving to Maui from Manhattan in the seventies, Susan and Chris Gebb have lovingly caring for their four-acre property tucked into the Ha‘iku forest. They chose it because it was pristine, never having been farmed or cultivated with chemicals. Sun powers the low-voltage electrical needs of the house, backed up by generator when necessary. The green-certified B&B sports one of the few gas-powered refrigerators on island.

Chris, a builder and architect, created the plantation-style home over the years, using mostly recycled materials from former military barracks that were torn down after WWII. Susan curates the property’s art and antiques, which add a layer of comfort and beauty to the cozy abode. She also oversees the sumptuous breakfasts served from 8 to 9 am for B&B guests.

Any of the three upstairs bedrooms of the main house can be rented individually. Most appealing is the spacious master bedroom with its own en suite bath, sitting area and a lanai with treetop views of the forest. Groups of eight or fewer can rent the entire house and enjoy use of the living and dining rooms, kitchen, and up- and downstairs lanais, which wrap the house and are wide enough for lounging or al fresco dining. Additional guests or family members might consider renting the honeymoon cottage, just a stone’s throw from the main house.



Wailea Sunset Bungalow

South Shore
Bedrooms: 2
Bathrooms: 1
» Oceanfront setting with private lawns
» Retro beach house with vintage Hawai‘i décor
» Deck with hot tub
» Walk to two sandy beaches
» Walk to Fairmont Kea Lani Resort

Cost: From $500/night
Contact: (888) 875-2818, ext. 6; info@TropicalVillaVacations.com

Searching for a little grass shack on the beach? Nothing fancy, just a two-bedroom bungalow where the only thing separating you from the ocean is an expansive emerald-green lawn, and the only question you need to entertain for the week is whether to relax in the hammock, hot tub or lawn chair?

It’s rare to find an affordable rental property in tony Wailea. Remarkably, we found this delightful bungalow right next door to Wailea Sunset Estate; you can rent it separately or in tandem with the larger house. Repeat guests have insisted that the owners retain its original 1960s charm, right down to the quirky front entrance that leads directly into the home’s only bathroom!

The decor may be from an earlier era, but the bungalow has all the modern amenities: air conditioning, a hot tub that combines privacy with ocean views, iPod docks, flat-screen TVs, al fresco dining, heated outdoor shower in the garden, even a Tassimo espresso machine. That adds up to a veritable haven for the Robinson Crusoe in us all.


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