Explore top 2026 5 Star Hotels in Upcountry Maui

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Top Upcountry Maui 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$813 nightly
The price is $965 total per night from Oct 25 to Oct 26
$965 total
Oct 25 - Oct 26
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, ...
Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

5 out of 5
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
$651 nightly
The price is $772 total per night from Oct 30 to Oct 31
$772 total
Oct 30 - Oct 31
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. ...
9.2/10 Wonderful! (1,284 reviews)
"Night staff not helpfully because no one is present at desk or gate. They had electric power backup for playing music and fancy lighting but not for room Air. I stayed 4 nights and 2 nights we had no power and no air ."

Reviewed on Oct 1, 2026

Opens in a new windowThe Westin Maui Resort & Spa, Ka'anapali
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$1,030 nightly
The price is $1,223 total per night from Oct 25 to Oct 26
$1,223 total
Oct 25 - Oct 26
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 ...
9.6/10 Exceptional! (1,000 reviews)
"Incredible service and high end property. The rooms are updated with a nice balcony. 3 pools and direct beach access makes it easy."

Reviewed on Sep 24, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from Oct 4 to Oct 5
$1,137 total
Oct 4 - Oct 5
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 ...
Opens in a new windowThe Ritz-Carlton Maui, Kapalua
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
3700 Wailea Alanui Dr Kihei HI
$646 nightly
The price is $767 total per night from Oct 30 to Oct 31
$767 total
Oct 30 - Oct 31
Total with taxes and fees
A full-service spa, 4 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a waterslide, ...
9/10 Wonderful! (1,001 reviews)
"Convenient location nd good staff at the concierge for tour bookings"

Reviewed on Sep 30, 2026

Opens in a new windowWailea Beach Resort - Marriott, Maui
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,118 nightly
The price is $1,327 total per night from Oct 23 to Oct 24
$1,327 total
Oct 23 - Oct 24
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 ...
Opens in a new windowFairmont Kea Lani Maui
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
555 Kaukahi Street, Maui Kihei HI
Fully refundableReserve now, pay when you stay
$840 nightly
The price is $997 total per night from Oct 31 to Nov 1
$997 total
Oct 31 - Nov 1
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, ...
9.4/10 Exceptional! (1,000 reviews)
"Everything was excellent, form the location to the incredible food!"

Reviewed on Sep 22, 2026

Opens in a new windowHotel Wailea Maui
The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui

5 out of 5
One Bay Drive Lahaina HI
$984 nightly
The price is $1,168 total per night from Nov 1 to Nov 2
$1,168 total
Nov 1 - Nov 2
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 ...
Opens in a new windowThe Resort at Kapalua Bay, Maui
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
$1,777 nightly
The price is $2,110 total per night from Oct 17 to Oct 18
$2,110 total
Oct 17 - Oct 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! (54 reviews)
"Amazing property with an incredible staff. A+++ all the way around!"

Reviewed on Aug 25, 2026

Opens in a new windowHo‘olei Villas at Grand Wailea
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
2780 Kekaa Drive Lahaina HI
Fully refundableReserve now, pay when you stay
$370 nightly
The price is $439 total per night from Nov 3 to Nov 4
$439 total
Nov 3 - Nov 4
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 ...
Opens in a new windowRoyal Lahaina Bungalows & Spa
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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

Maui Coast Hotel

Maui Coast Hotel

4 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Room was outdated but the amenities are great."
A verified traveler stayed at Maui Coast Hotel
Maui Coast Hotel

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