Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Compare Upcountry Maui 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1001)
"Beautiful resort with amazing views of the ocean. Staff went above and beyond to make our stay memorable. Area is excellent for walking running etc. outdoor mall only minutes away with great restaurants and shopping. The Wailea area is stunning. We will be back. "
The price is NT$30,099
NT$37,307 total
includes taxes & fees
Feb 2 - Feb 3
Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Great service. Excellent resort experience. Had an issue with drainage worms in the shower of the first room. Four Seasons upgraded us to a better room after issue was identified. "
The price is NT$23,597
NT$27,835 total
includes taxes & fees
Feb 3 - Feb 4
Four Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua
3 outdoor pools, cabanas (surcharge), sun loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1001)
"I liked the pool it was incredible"
The price is NT$29,117
NT$36,148 total
includes taxes & fees
Jan 23 - Jan 24
The Ritz-Carlton Maui, Kapalua
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (996)
"Hotel Wailea is a gem! Beautiful grounds and stunning architectural designs! Impeccable service and attention to guest needs. No better hotel in Maui!"
The price is NT$34,357
NT$42,460 total
includes taxes & fees
Feb 1 - Feb 2
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (193)
"Our stay was amazing! I can’t say enough great things about the accommodations and the staff. The only thing I had a hard time with was the valet parking. The constant in and out every time you just want to stop by for an hour to change for dinner or something is a hassle with dropping the car off and requesting it again. Other than that it was fabulous!"
The price is NT$42,316
NT$53,377 total
includes taxes & fees
Feb 11 - Feb 12
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun loungers

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (38)
"Best property in Maui "
The price is NT$63,529
NT$77,067 total
includes taxes & fees
Jan 27 - Jan 28
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
View from property

Fairmont Kea Lani Maui Villa Experience

5.0 star property
9.6 out of 10, Exceptional, (4)
"It’s a decent hotel to stay for the family."
The price is NT$72,632
NT$87,602 total
includes taxes & fees
Jan 26 - Jan 27
Fairmont Kea Lani Maui Villa Experience
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upcountry Maui.
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy, Lahaina, HI
The price is NT$20,573 per night from Jan 26 to Jan 27
NT$20,573
NT$26,162 total
includes taxes & fees
Jan 26 - Jan 27
8.8/10 Excellent! (659 reviews)
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Upcountry Maui?
The amount you pay for a 5-star hotel in Upcountry Maui can vary according to when you decide to travel and how long you plan to stay, among a number of factors. Use our price per night filter and other search tools to find the best rate on a plush stay.

  • Search for the lowest price per night from NT$20,573

What makes a hotel 5 stars in Upcountry Maui?
Faultless guest service is at the heart of every 5-star hotel in Upcountry Maui. From the minute you step through the door, staff are at your beck and call, whether arranging valet parking or providing a nightly turn-down service. In addition, hotels have to feature top-rate conveniences to qualify for a 5-star rating. These can include luxury baths, spas or saunas, swimming pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Use Expedia’s filters to find a high-end retreat in Upcountry Maui where everything you need is included. After your initial search, narrow down your results for properties that have 5 stars and are deemed “All inclusive.” The main thing on the agenda at these stays? Pure relaxation and indulgence.
Are there any 5-star vacation rentals in Upcountry Maui?
Although you won’t find any 5-star vacation rentals in Upcountry Maui on our site, we have a range of retreats that promise an unforgettable getaway. Discover one that suits your needs by checking out our vacation rentals in Upcountry Maui.