Luxury Vacation Rentals with a Private Pool 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 2 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Kihei

Home in Kihei

2 bedrooms•2 baths

Luxury

Home in Kihei

4 bedrooms•3.5 baths

Welcome to private poolside luxury in Kihei

Welcome to a new level of island living. Wander’s luxury private-pool vacation rentals in Kihei pair five-star polish with the privacy of a modern home. Picture contemporary villas with glass-lined great rooms, sun-warmed lanais, and pools positioned for golden-hour swims.

Expect chef-ready kitchens, spa-like primary suites, and seamless indoor-outdoor flow, all supported by pristine cleaning, ultra fast WiFi, and 24/7 concierge. Many homes include fitness spaces, hot tubs, and outdoor showers set steps from your pool for an easy, elevated routine. What you see is exactly what awaits, so settling in feels instant and effortless.

Available soon in Kihei

Home in Kihei

2 bedrooms•2 baths

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Featured private pool vacation rentals in Kihei

Luxury

Home in Kihei

4 bedrooms•3.5 baths

Highlights in Kihei

Discover sun-drenched beaches, vibrant coral reefs, and a relaxed aloha spirit in this charming coastal town on Maui's south shore.

Kamaole Beach Parks

Molokini Crater

Keawakapu Beach

Maui Brewing Company

Hawaiian Islands Humpback Whale National Marine Sanctuary

Kalama Park

Kihei Kalama Village

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

Home in Kihei

2 bedrooms•2 baths

Luxury

Home in Kihei

4 bedrooms•3.5 baths

View all homes

Most popular amenities for private pool vacation rentals in Kihei

Outdoor dining area (2)

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Discover more beyond the pool in Kihei

Set on Maui’s south shore, Kihei is known for long stretches of golden sand and some of the island’s sunniest skies. Mornings are calm and clear, afternoons bring a soft trade wind, and winter often delivers whale sightings just offshore.

The trio of Kamaole Beach Parks anchors relaxed beach days, while nearby Wailea adds championship golf, upscale shopping, and refined dining. Boats to Molokini depart from the Kihei Boat Ramp, and sunsets glow over Kahoʻolawe and Lānaʻi. With easy access to coastal adventures and laid-back town rhythms, this is why Wander’s luxury private-pool 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 private pool vacation rentals?

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

Some of our most popular private pool vacation rentals in Kihei include Beach Walk, Wander Maui Meadows, and Beach Walk. 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 private pool vacation rentals does Wander have available in Kihei?

Wander offers 2 private pool 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 private pool vacation rentals in Kihei?

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

Do Wander’s private pool 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.