Explore top 2025 5 Star Hotels in Upcountry Maui

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Top Upcountry Maui 5 Star hotels

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI

$1,119 nightly

$1,320 total

Oct 25 - Oct 26

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! (1,013 reviews)

"Gorgeous place"

Reviewed on Sep 23, 2025

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

$702 nightly

$828 total

Oct 21 - Oct 22

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! (1,015 reviews)

"Stunning resort!"

Reviewed on Sep 15, 2025

The Ritz-Carlton Maui, Kapalua

1 Ritz-Carlton Drive, Kapalua, HI

$944 nightly

$1,114 total

Oct 17 - Oct 18

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! (1,008 reviews)

"Location"

Reviewed on Sep 22, 2025

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI

$755 nightly

$891 total

Oct 27 - Oct 28

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)

"Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again."

Reviewed on Sep 24, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street, Kihei, HI

$949 nightly

$1,119 total

Sep 29 - Sep 30

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! (1,000 reviews)

"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!"

Reviewed on Aug 27, 2025

Montage Kapalua Bay

One Bay Drive, Lahaina, HI

$1,074 nightly

$1,286 total

Oct 18 - Oct 19

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! (201 reviews)

"Super nice"

Reviewed on Jun 16, 2025

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle, Kihei, HI

$2,081 nightly

$2,455 total

Sep 30 - Oct 1

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! (41 reviews)

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

Reviewed on Jun 15, 2025

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A, Kihei, HI

$2,789 nightly

$3,290 total

Sep 30 - Oct 1

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! (4 reviews)

"Amazing property- very updated and clean. Comfortable beds. Condo had very well stocked kitchen and all the additional items we can’t travel with ( beach chairs, beach towels, umbrellas, and coolers). The 3rd floor patio overlooks the pool which is great to keep an eye on the kids. Direct views to ..."

Reviewed on Jul 18, 2025

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Wailea Luxury Hilltop Resort Vistas

10 Wailea Ekolu Pl, Kihei, HI

This apartment features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.

"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back!"

Reviewed on Nov 28, 2024

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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.

Recent Upcountry Maui hotel reviews by fellow wanderers

Royal Lahaina Resort & Bungalows

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"We had an AMAZING time on our stay, the room Was beautiful, view was spectacular, staff was so sweet and friendly. Can’t recommend it enough! Easy transportation via free shuttle the the nearby resorts and whalers village. Overall great place to stay!"

A verified traveler stayed at Royal Lahaina Resort & Bungalows

Aston Kaanapali Shores

5 out of 5

Posted 5 days ago

Travelocity Verified Review

"We had the best sunsets from our ocean view balcony. It was nice to have a little beach in front of the hotel & uncrowded. The property was really clean & the landscaping was beautifully kept. It was nice that they had local vendors come into the hotel once a week with local crafts & art."

A verified traveler stayed at Aston Kaanapali Shores