Luxury Vacation Rentals for Families in Kihei

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 6 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Kihei

Wander Wailea Oceanview

Welcome to family adventures in Kihei

Bring your crew to Kihei with space to spare. Our luxury family vacation rentals in Kihei combine resort polish with the ease of a private home, so grandparents, parents, and kids can settle in comfortably.

Expect multiple ensuite bedrooms and bunk rooms for the little ones, chef-caliber kitchens for big breakfasts, indoor-outdoor lanais, and private pools or hot tubs. Families appreciate child-friendly touches like blackout shades, high chairs and pack-and-plays on request, fenced lawns, ultrafast WiFi, quiet work nooks, and full laundry. With pristine cleaning and 24/7 concierge, a Wander stay always looks like the photos and frees you to focus on time together.

Popular family vacation rentals in Kihei

Wander Wailea Oceanview

Featured family vacation rentals in Kihei

Highlights in Kihei

Discover sun-drenched beaches with gentle waves, incredible marine life, and a laid-back atmosphere perfect for your next family getaway.

Kamaole Beach Park III

Maui Ocean Center, The Aquarium of Hawaii

Keawakapu Beach

Hawaiian Islands Humpback Whale National Marine Sanctuary

Molokini Crater Snorkeling

Kalepolepo Beach Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kihei

Wander Wailea Oceanview

Most popular amenities for family vacation rentals in Kihei

Exercise Equipment (2)

Outdoor Dining Area (6)

Mountain View (1)

Bbq Area (5)

Fire Pit (3)

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Discover more family fun in Kihei

On Maui’s sunny south shore, Kihei greets families with gentle mornings, swimmable water, and wide golden beaches. Lifeguarded Kamaole parks line the coast with soft sand and grassy lawns, while clear-water coves make it easy for beginners to spot reef fish. Winter brings humpback whales just offshore and radiant sunsets year-round.

Beyond the beach, you’ll find calm conditions for paddling, laid-back cafes and shave ice, and quick access to Wailea golf, Maalaea Harbor outings, and scenic island drives. The relaxed rhythm keeps logistics easy for multigenerational trips and little travelers alike. This is why Wander’s luxury vacation rentals in Kihei are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Kihei

Why should I book a Wander in Kihei over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.

Every home in Kihei delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Kihei?

Some of our most popular family vacation rentals in Kihei include Wander Maui Meadows, Wander Kihei Shores, and Wander Wailea Elua. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Kihei?

Wander offers 6 family vacation rentals in Kihei, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Kihei?

You can check-in to Wander family vacation rentals in Kihei after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Kihei have WiFi access?

Yes. Every Wander home in Kihei has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.