Explore top 2026 5 Star Hotels in Upcountry Maui

Name: Aloha Chic Penthouse Vistas
Rating: 10

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Top Upcountry Maui 5 Star hotels

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,149 nightly

$1,364 total

Jul 11 - Jul 12

Total with taxes and fees

A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's ...

9.4/10 Exceptional! (1,000 reviews)

"Breathtaking place!"

Reviewed on Jul 2, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$865 nightly

$1,027 total

Jul 16 - Jul 17

Total with taxes and fees

A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers ...

8.8/10 Excellent! (1,001 reviews)

Reviewed on Jul 3, 2026

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$1,000 nightly

$1,187 total

Jul 10 - Jul 11

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and ...

9.6/10 Exceptional! (1,002 reviews)

"This resort was ultra luxury. Staff was very attentive and respectful."

Reviewed on Jul 3, 2026

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$858 nightly

$1,019 total

Jul 24 - Jul 25

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 6 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. There's ...

9.2/10 Wonderful! (1,002 reviews)

"We had a great stay!"

Reviewed on Jul 3, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$737 nightly

$875 total

Jul 11 - Jul 12

Total with taxes and fees

This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...

9.4/10 Exceptional! (1,000 reviews)

"If there isn’t a wedding going on watch the sunset from the front lawn area by the old ice cream truck. Better view than from the birdcage. More open and less blockage. Great high end vibe."

Reviewed on Jun 22, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,186 nightly

$2,595 total

Jul 17 - Jul 18

Total with taxes and fees

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...

9.6/10 Exceptional! (48 reviews)

"Pools are great, the villa is perfect for families, service was good, and the F&B options are outstanding"

Reviewed on Jun 14, 2026

The Resort at Kapalua Bay, Maui

One Bay Drive Lahaina HI

$1,624 nightly

$1,928 total

Jul 29 - Jul 30

Total with taxes and fees

A full-service spa, 5 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a children's ...

9.6/10 Exceptional! (213 reviews)

"Very accommodating hotel with wonderful staff and amazing view. Gluten free also!"

Reviewed on Jun 4, 2026

Royal Lahaina Bungalows & Spa

2780 Kekaa Drive Lahaina HI

Fully refundableReserve now, pay when you stay

$393 nightly

$466 total

Jul 5 - Jul 6

Total with taxes and fees

A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are all featured at this luxury aparthotel. Enjoy beachfront dining and relax with beach cabanas ...

8/10 Very Good! (18 reviews)

"Not a bad place for a 2-3 day stay! However, front desk staff could’ve been better in providing the only thing that they’re for — the service with a smile; the gentleman who checked us in absolutely had not patience in listening to his guests at all - let alone greeting guests with a SMILE!"

Reviewed on Jul 2, 2026

Oceanfront Kihei Paradise Vistas

938 S Kihei Rd Kihei HI

This apartment features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

10/10 Exceptional! (3 reviews)

"The apartment is newly remodeled. Very nice, bright, clean, with stunning views into the ocean. All super well equipped with anything you possibly need. We personally appreciated the beach chairs, beach umbrellas, thermal backpack and tons of towels. Also, anything you might ever need in the kitchen ..."

Reviewed on Jun 28, 2026

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Aloha Chic Penthouse Vistas

938 S Kihei Rd Kihei HI

This condo features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

10/10 Exceptional! (5 reviews)

"The place was beautiful, clean, and well equipped with supplies. The location was perfect for us with amazing views and sunsets."

Reviewed on Jul 3, 2026

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Upcountry Maui Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Upcountry Maui to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Upcountry Maui 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Upcountry Maui before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Upcountry Maui hotel reviews by fellow wanderers

Hyatt Regency Maui Resort & Spa

5 out of 5

Posted 2 hours ago

Travelocity Verified Review

"The property itself is well maintained and with good amenities. It's very close to the beach."

A verified traveler stayed at Hyatt Regency Maui Resort & Spa

Royal Lahaina Resort & Bungalows

5 out of 5

Posted 3 hours ago

Travelocity Verified Review

"Although we had reserved a bungalow, we were told upon arrival that we had been upgraded to a suite on a high floor in the tower....which turned out to be beautiful and spacious. The facility itself was lovely and clean; the staff were universally personable, professional, and helpful; and the grounds were very attractive and well maintained. Our stay was for only one night as we had other accommodations for the remainder of our time in Maui, but I would have no hesitation at all to choose Royal Lahaina again for future visits."

A verified traveler stayed at Royal Lahaina Resort & Bungalows

Grand Wailea Maui, A Waldorf Astoria Resort

4 out of 5

Posted 15 hours ago

Travelocity Verified Review

"It’s just not the same…. Like so many things these days it just isn’t up to the standards it once was for luxury, quality and service. This was my fifth trip to the Grand Wailea since it originally opened. The grounds were still mostly beautiful although many tiki torches were nonfunctioning, handrails missing, cracked, missing tiles at the adult pool was particularly sad to see and areas within the grounds that just seemed unkept, especially around the old Asian restaurant, which is now shuttered/abandoned. Upon arrival, I immediately knew that something was a miss when the incredible waterfall that sets the tone for the grandeur that was always promised was inoperative. The staff says it has been broken for over a year and has not been fixed. This was the center piece of the tropical experience for me. It is this lack of maintenance that would keep me from going back to the Grand Wailea as it is no longer a five star resort, even after their $350 million partial resort renovation. Our ocean view room was large and comfortable, but the decor was as basic as a Holiday Inn. One picture, one decorative mirror was all the design afforded. You could tell they’ve cut way back on staff too. It is still a worthy of at least one holiday if your priority is to enjoy the extensive pools, spa, etc. If you’re truly looking for a five star experience, the Four Seasons is a better choice."

A verified traveler stayed at Grand Wailea Maui, A Waldorf Astoria Resort