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

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$795 nightly

$944 total

Jan 4 - Jan 5, 2026

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! (999 reviews)

This property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on Dec 2, 2025

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$740 nightly

$878 total

Jan 11 - Jan 12, 2026

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! (1,003 reviews)

Very nice resort for a family vacation!

Reviewed on Dec 23, 2025

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$908 nightly

$1,077 total

Jan 12 - Jan 13, 2026

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)

Room was very clean, staff accommodated every needs, view of the ocean was amazing. Kids and family friendly. Buffet breakfast always fresh fruits.

Reviewed on Dec 24, 2025

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive Kapalua HI

$854 nightly

$1,013 total

Jan 4 - Jan 5, 2026

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! (1,000 reviews)

Top notch property with amazing service and staff

Reviewed on Dec 22, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$1,099 nightly

$1,305 total

Jan 4 - Jan 5, 2026

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)

This resort with private villas is spectacular. The rooms are beautifully appointed and perfectly clean with every amenity you need. We stayed in #52 that overlooked a lagoon and it couldn't have been nicer or more peaceful. Even though there are also ocean views, this was my favorite. The staff ...

Reviewed on Dec 26, 2025

Montage Kapalua Bay

One Bay Drive Lahaina HI

$1,441 nightly

$1,744 total

Jan 26 - Jan 27, 2026

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

$2,060 nightly

$2,445 total

Jan 24 - Jan 25, 2026

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

$488 nightly

$579 total

Jan 3 - Jan 4, 2026

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 ...

9/10 Wonderful! (2 reviews)

Clean room and staff is super friendly. Would stay here again

Reviewed on Dec 21, 2025

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

$2,939 nightly

$3,467 total

Jan 8 - Jan 9, 2026

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.