Explore top 2026 5 Star Hotels in Upcountry Maui

Name: 2 2 Oceanview Modern Resort Vistas
Rating: 10

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Top Upcountry Maui 5 Star hotels

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,068 nightly

$1,268 total

Aug 19 - Aug 20

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 ...

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$786 nightly

$933 total

Aug 31 - Sep 1

Total with taxes and fees

A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, ...

8.6/10 Excellent! (1,001 reviews)

"This was a lovely stay. We ended up in the Napua wing and it truly was great. The staff was very kind and remembered our names instantly. A lazy river should come with every hotel hahaha!"

Reviewed on Aug 14, 2026

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI

Fully refundableReserve now, pay when you stay

$651 nightly

$772 total

Aug 21 - Aug 22

Total with taxes and fees

A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this luxury hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. ...

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$880 nightly

$1,045 total

Aug 31 - Sep 1

Total with taxes and fees

A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. There's fun for all ages with a free kid's club and a children's ...

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$858 nightly

$1,019 total

Aug 28 - Aug 29

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 6 restaurants. There's fun for all ages with a children's pool and a playground, and families ...

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$817 nightly

$970 total

Aug 31 - Sep 1

Total with taxes and fees

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

9.4/10 Exceptional! (1,004 reviews)

"Great atmosphere relaxing,.quiet & beautiful!"

Reviewed on Aug 16, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$1,776 nightly

$2,108 total

Sep 1 - Sep 2

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, ...

Royal Lahaina Bungalows & Spa

2780 Kekaa Drive Lahaina HI

Fully refundableReserve now, pay when you stay

$378 nightly

$448 total

Aug 19 - Aug 20

Total with taxes and fees

A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are all featured at this luxury aparthotel. Unwind with a drink at one of the 2 bars/lounges ...

8.2/10 Very Good! (24 reviews)

"The moment we checked in the staff was attentive and gracious. Very accommodating, making our Hawaiian vacation a dream."

Reviewed on Aug 13, 2026

The Resort at Kapalua Bay, Maui

One Bay Drive Lahaina HI

$884 nightly

$1,049 total

Aug 27 - Aug 28

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 ...

2 2 Oceanview Modern Resort Vistas

938 S Kihei Rd Kihei HI

This condo features an outdoor pool and a hot tub. Free self parking, laundry facilities, and a virtual front desk are also on offer.

10/10 Exceptional! (11 reviews)

"What an amazing stay. This a review that I am happy to leave....The apartment was spacious, comfortable and had everything we could possibly need. Pictures are absolutely accurate. It was such a relief to come home to a cool apartment, our snacks in the kitchen, 2 showers, so no wait..... Beach supplies, ..."

Reviewed on Jul 23, 2026

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Royal Lahaina Resort & Bungalows

5 out of 5

Posted less than an hour ago

Travelocity Verified Review

"Wonderful staff"

A verified traveler stayed at Royal Lahaina Resort & Bungalows

Hyatt Regency Maui Resort & Spa

5 out of 5

Posted 13 hours ago

Travelocity Verified Review

"The staff was amazing. Clean and well maintained. The hotel boasts 6 outdoor pools but that is not exactly true…2 w/a hot tub and 3 and the adjacent Hyatt vacation club that they said we had could use. (We didn’t) Not much for beach access in front of the hotel, but an easy walk to food, shopping, surfing, snorkeling and just perfect waves!"

A verified traveler stayed at Hyatt Regency Maui Resort & Spa

Wailea Beach Resort - Marriott, Maui

4 out of 5

Posted 2 days ago

Travelocity Verified Review

"The property was amazing for kids with multiple water slides, arcade room, and many different pool and beach options. The hotel location was great and grounds are beautiful. The big building where our room was located is older and less upkept - the AC couldn’t cool the room and we saw a cockroach. Strongly suggest to splurge for the more modern rooms in the two story buildings. The beach chair process is lengthy: waited in line from 7:40 to 8am and was the last to get an umbrella; then another 45 min in next line for umbrella to be set up. Even though there were 4 of us, you only get 1 umbrella and two chairs per room. Ulua beach was great (no chair setup available) and we ended up snorkeling the reef on the right side of it seeing lots of fish and a turtle. The food around was commercial and overpriced. Humble kitchen dinner was just average and not worth the price. But then again everything in that area is super pricy and average. Overall, would choose this location again for its location, and grounds, and kids activities but would splurge for better room in newer buildings and would go for food into the plazas 15 min drive away"

A verified traveler stayed at Wailea Beach Resort - Marriott, Maui

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"This was a lovely stay. We ended up in the Napua wing and it truly was great. The staff was very kind and remembered our names instantly. A lazy river should come with every hotel hahaha!"

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