Explore top 2026 5 Star Hotels in Upcountry Maui

Name: 2 2 Oceanview Modern Resort Vistas
Rating: 9.8

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Top Upcountry Maui 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$914 nightly

$1,085 total

Mar 5 - Mar 6

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! (1,002 reviews)

Having multiple pool options available just steps away from the beach was amazing! The outdoor lobby is the epitome of island paradise and the overall setting is just gorgeous!

Reviewed on Mar 2, 2026

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$1,135 nightly

$1,347 total

Mar 21 - Mar 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! (1,004 reviews)

Staff

Reviewed on Feb 28, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$993 nightly

$1,178 total

Mar 7 - Mar 8

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! (1,001 reviews)

The stay was great. Had a pool side room with our own lounge chairs and table. Very relaxing, and highly recommend the room. Clean, well laid out, cleaning services daily were well done. This review doesn't ask about the restaurants, so will write it here. While I can recommend the resort, and the ...

Reviewed on Mar 2, 2026

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$1,238 nightly

$1,470 total

Mar 4 - Mar 5

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)

This is the worst Ritz I have ever been at!!! The beds where horrible the food was terrible and the property was old and run down!!

Reviewed on Mar 2, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$1,129 nightly

$1,340 total

Mar 16 - Mar 17

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! (1,001 reviews)

abslout great

Reviewed on Feb 26, 2026

Montage Kapalua Bay

One Bay Drive Lahaina HI

$1,608 nightly

$1,909 total

Mar 4 - Mar 5

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! (208 reviews)

Staff was great. Some maintenance issues, leaking water dispenser on fridge leading to pooling and warping of floor. Same on large lanai. Otherwise, great

Reviewed on Feb 14, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,185 nightly

$2,594 total

Mar 5 - Mar 6

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! (45 reviews)

Womderful home, terrific service, access to hotel amenities was key.

Reviewed on Feb 28, 2026

Royal Lahaina Bungalows & Spa

2780 Kekaa Drive Lahaina HI

Fully refundableReserve now, pay when you stay

$390 nightly

$463 total

Apr 2 - Apr 3

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 ...

9.6/10 Exceptional! (5 reviews)

Staff was excellent and very responsive. The grounds were stunning and well taken care of, rooms could be cleaner bu the location is excellent.

Reviewed on Feb 13, 2026

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.

9.8/10 Exceptional! (7 reviews)

The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful!

Reviewed on Dec 26, 2025

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Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

$3,458 nightly

$4,106 total

Mar 5 - Mar 6

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 ...

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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.