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 7 private pool vacation rentals – enter your dates for availability.
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Kihei, HI, US
Wander Wailea Shores
14
Kihei, HI, US
Wander Wailea Oceanview
Next avail.
Mar 8 - Mar 16
26
Kihei, HI, US
Wander Wailea Palms
Next avail.
Dec 14 - Dec 16
26
Kihei, HI, US
Wander Kihei Dunes
Next avail.
Feb 21 - Mar 1
26
Kihei, HI, US
Wander Kihei Shores
24
Kihei, Hawaii
Wander Maui Meadows
Next avail.
Mar 1 - Mar 6
410
4.8
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.
Kihei, Hawaii
Wander Maui Meadows
Next avail.
Mar 1 - Mar 6
410
4.8
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Kihei, HI, US
Wander Wailea Shores
14
Kihei, HI, US
Wander Wailea Oceanview
Next avail.
Mar 8 - Mar 16
26
Kihei, HI, US
Wander Wailea Palms
Next avail.
Dec 14 - Dec 16
26
Kihei, HI, US
Wander Kihei Dunes
Next avail.
Feb 21 - Mar 1
26
Kihei, HI, US
Wander Kihei Shores
24
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.
All homes in Kihei
Kihei, HI, US
Wander Wailea Elua
Next avail.
Jan 18 - Jan 26
36
Kihei, HI, US
Wander Wailea Shores
14
Kihei, HI, US
Wander Wailea Oceanview
Next avail.
Mar 8 - Mar 16
26
Kihei, HI, US
Wander Wailea Palms
Next avail.
Dec 14 - Dec 16
26
Kihei, HI, US
Wander Kihei Dunes
Next avail.
Feb 21 - Mar 1
26
Kihei, HI, US
Wander Kihei Shores
24
Kihei, Hawaii
Wander Maui Meadows
Next avail.
Mar 1 - Mar 6
410
4.8
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.