TOP Hotels with Pools in Upcountry Maui, HI for 2026 - Upcountry Maui Hotels with a Pool

View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds.
#AboveItAll

Check availability on Upcountry Maui Hotels with Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Upcountry Maui hotels with a pool

Lumeria Maui Educational Retreat Center

Makawao

Swim and stretch in paradise at this serene retreat, where an outdoor pool meets lush gardens and wellness activities await you.

includes taxes & fees

4 Mar - 5 Mar

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Makawao

includes taxes & fees

4 Mar - 5 Mar

Kohea Kai Hotel Maui

North Kihei

Tropical pool oasis minutes from Kamaole Beach with sun loungers and ocean adventure possibilities.

includes taxes & fees

1 Apr - 2 Apr

Maui Seaside Hotel

Kahului

Outdoor island pool haven offers steps-to-beach luxury with volcano views and fire pits.

includes taxes & fees

9 Mar - 10 Mar

Outdoor pool, pool umbrellas, pool loungers

Courtyard Maui Kahului Airport

Kahului

Splash into sunshine at this hotel's tropical pool oasis, where loungers and umbrellas await your relaxation.

includes taxes & fees

8 Mar - 9 Mar

Maui Beach Hotel

Kahului

Pool paradise meets island escape at this hotel's sun-drenched oasis just steps from the beach.

includes taxes & fees

1 Apr - 2 Apr

The Mauian - Boutique Beach Studios on Napili Bay

Lahaina

Refreshing tropical oasis awaits at this boutique beachfront hotel with stylish pool loungers and warm waters.

Bright, Beautiful, Remodeled Island Sands 505 Condo

Wailuku

includes taxes & fees

4 Mar - 5 Mar

View all properties

Choose what matters most at hotels with a pool in Upcountry Maui

Breakfast included

4 stars

Top Upcountry Maui Hotel Reviews

Maui Coast Hotel

10/10 Excellent

"Room was spacious, with comfortable furniture and plenty of storage spaces. The pool area was also comfortable, and easy to hang out in."

Wailea Beach Resort - Marriott, Maui

10/10 Excellent

"The resort was beautiful and the staff were so helpful and kind. It was truly wonderful. I recommend (for first timers) download the resort’s app, it makes getting around easier—the place is massive and the layout can be tricky. But we loved it here and hope to visit again!!"