Explore top 2025 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

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI

$755 nightly

$891 total

Nov 21 - Nov 22

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! (1,000 reviews)

Great Service

Offered turn down service; the staff went above any beyond to ensure that we were comfortable.

Reviewed on Oct 26, 2025

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive, Kapalua, HI

$754 nightly

$889 total

Dec 12 - Dec 13

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 ...

9/10 Wonderful! (1,002 reviews)

Great staff. All very friendly.

Reviewed on Oct 26, 2025

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

$647 nightly

$763 total

Nov 30 - Dec 1

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! (1,007 reviews)

Great hotel

Reviewed on Nov 9, 2025

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI

$814 nightly

$960 total

Nov 29 - Nov 30

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! (1,002 reviews)

Perfect for our honeymoon. The standard room was large and updated. Pools were great and weren’t crowded. Staff was fantastic

Reviewed on Nov 9, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street, Kihei, HI

Fully refundableReserve now, pay when you stay

$949 nightly

$1,119 total

Nov 30 - Dec 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 business center, laundry service, and valet ...

9.2/10 Wonderful! (1,001 reviews)

Lovely room and property, friendly staff, excellent amenities (on site dining, shuttle service, beautiful pool and hot tub.) Offers a more secluded, romantic and quieter Maui experience than the typical Wailea lodging. Unique Birdcage Restaurant and bar was an added plus for us.

Reviewed on Nov 6, 2025

Montage Kapalua Bay

One Bay Drive, Lahaina, HI

$1,069 nightly

$1,286 total

Dec 7 - Dec 8

Total with taxes and fees

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

9.6/10 Exceptional! (204 reviews)

Super nice

Reviewed on Jun 16, 2025

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle, Kihei, HI

$1,861 nightly

$2,196 total

Dec 2 - Dec 3

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! (43 reviews)

Perfect for Families. Quite spacious and great for a relaxing Family vacation.

Reviewed on Jun 15, 2025

Royal Lahaina Bungalows & Spa

2780 Kekaa Drive, Lahaina, HI

Fully refundableReserve now, pay when you stay

$317 nightly

$374 total

Dec 7 - Dec 8

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 ...

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A, Kihei, HI

$3,049 nightly

$3,596 total

Dec 12 - Dec 13

Total with taxes and fees

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with beach cabanas ...

9.6/10 Exceptional! (6 reviews)

It’s a decent hotel to stay for the family.

Reviewed on Aug 22, 2024

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! (5 reviews)

Great/convenient location with awesome views!! Spotless, comfortable and they even provided welcome Hawaiian cookies and coffee! Also extra beach chairs, coolers, games, etc. Beds were very comfy. A/C worked great. Close to Pickleball if you like to play. The competition is varied but mostly strong ...

Reviewed on Oct 8, 2025

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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.