Luxury Vacation Rentals 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 7 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Kihei

Wander Wailea Oceanview

Welcome to Kihei

Elevate your escape with Wander’s luxury vacation rentals in Kihei. On Maui’s sunlit south shore, our collection blends the polish of a five-star stay with the privacy of a beautiful home. Expect bright, contemporary spaces that frame the Pacific and invite indoor-outdoor living.

Every Wander includes ultra fast WiFi, hotel-grade linens, pristine cleaning, 24/7 concierge, and thoughtfully equipped kitchens. Many offer private pools, fitness areas, and seamless smart-home features, ideal for blending work and play.

Book with confidence. Our homes look exactly like the photos and are expertly operated, so your time in Kihei starts relaxed and effortless.

Destinations near Kihei

Popular vacation rentals in Kihei

Wander Wailea Oceanview

Featured vacation rentals in Kihei

Highlights in Kihei

Discover sunny shores, vibrant coral reefs, and breathtaking sunsets in this laid-back South Maui coastal town.

Kamaole Beach Parks

Keawakapu Beach

Molokini Crater

Hawaiian Islands Humpback Whale National Marine Sanctuary

Kihei Kalama Village

Maui Nui Brewing Company

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 vacation rentals in Kihei

Exercise Equipment (3)

Outdoor Dining Area (7)

Mountain View (1)

Bbq Area (6)

Other popular amenities & vacation types in Kihei

Family vacation rentals in Kihei

Hot tub vacation rentals in Kihei

Private pool vacation rentals in Kihei

Discover more of Kihei

Set along a stretch of golden coastline, Kihei delivers sun-splashed days and calm mornings shaped by Haleakala’s rain shadow. Miles of shoreline invite leisurely swims and paddle sessions, with the Kamaole Beach Parks offering soft sand and clear water. Winter brings humpback whales within view just offshore.

Beyond the beach, browse local markets, catch fiery sunsets over Kaho‘olawe, or set out to nearby Wailea, Makena, and Ma‘alaea for golf, snorkeling, and island excursions. The relaxed pace pairs with easy access to Maui’s best, making Kihei a refined yet laid-back base. 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 vacation rentals?

Wander offers a level of consistency and quality you won’t find with most 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 vacation rentals in Kihei?

Some of our most popular vacation rentals in Kihei include Wander Maui Meadows, Wander Wailea Elua, and Wander Wailea Shores. 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 vacation rentals does Wander have available in Kihei?

Wander offers 7 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 vacation rentals in Kihei?

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

Do Wander’s 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.