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Top Upcountry Maui 5 Star hotels

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,149 nightly
The price is $1,364 total per night from Jul 11 to Jul 12
$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

Opens in a new windowFairmont Kea Lani Maui
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$865 nightly
The price is $1,027 total per night from Jul 16 to Jul 17
$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)
"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 ..."

Reviewed on Jul 3, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$1,000 nightly
The price is $1,187 total per night from Jul 10 to Jul 11
$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

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
$858 nightly
The price is $1,019 total per night from Jul 24 to Jul 25
$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

Opens in a new windowThe Ritz-Carlton Maui, Kapalua
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
$737 nightly
The price is $875 total per night from Jul 11 to Jul 12
$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

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
$2,186 nightly
The price is $2,595 total per night from Jul 17 to Jul 18
$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

Opens in a new windowHo‘olei Villas at Grand Wailea
The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui

5 out of 5
One Bay Drive Lahaina HI
$1,624 nightly
The price is $1,928 total per night from Jul 29 to Jul 30
$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

Opens in a new windowThe Resort at Kapalua Bay, Maui
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
2780 Kekaa Drive Lahaina HI
Fully refundableReserve now, pay when you stay
$393 nightly
The price is $466 total per night from Jul 5 to Jul 6
$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

Opens in a new windowRoyal Lahaina Bungalows & Spa
Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas

5 out of 5
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

Opens in a new windowOceanfront Kihei Paradise Vistas
Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas

5 out of 5
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

Opens in a new windowAloha Chic Penthouse Vistas
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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.

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