Find 5 Star Hotels in Upcountry Maui, HI from SAR 1,389

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

The Ritz-Carlton Maui, Kapalua
Outdoor pool

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1005)
"Had a wonderful stay for our anniversary and we definitely will be back! The service was impeccable and everyone was SO friendly wherever we went in the hotel, even the housekeeping when passing in the halls. It's so rare these days, even in top hotels. Breakfast was a little overpriced for the ala carte menu, but the food in every restaurant was very good. Had the best massage of my life at the spa (Holly is AMAZING) and wished we had planned to spend more time there. Have stayed at other...
The price is SAR 2,699
SAR 3,391 total
includes taxes & fees
1 Dec - 2 Dec
The Ritz-Carlton Maui, Kapalua
Four Seasons Resort Maui at Wailea
Exterior

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1001)
"Excellent customer service "
The price is SAR 2,985
SAR 3,521 total
includes taxes & fees
30 Nov - 1 Dec
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
Exterior

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1001)
"Beautiful, well maintained, best pool on island."
The price is SAR 2,962
SAR 3,701 total
includes taxes & fees
1 Dec - 2 Dec
Grand Wailea Maui, A Waldorf Astoria Resort
Hotel Wailea, Relais & Chateaux - Adults Only
Pool

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (981)
"Great place to rest and enjoy the island. Very quiet and relaxed place. The only down side would be very limited dining option in the resort. Restaurants are very, very expensive but they do not offer many options for dining. Not a great kind of restaurant for a hotel resort. You can go once maybe twice and eat, and you already tried everything on the menu. Two person dinner at least $450 and breakfast at least $150-$200 which is just too crazy. "
The price is SAR 3,938
SAR 4,867 total
includes taxes & fees
3 Dec - 4 Dec
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
Exterior

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 SAR 3,976
SAR 4,955 total
includes taxes & fees
13 Dec - 14 Dec
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Pool

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (37)
"Best property in Maui "
The price is SAR 5,914
SAR 7,219 total
includes taxes & fees
11 Dec - 12 Dec
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
Exterior

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 SAR 7,784
SAR 9,402 total
includes taxes & fees
23 Nov - 24 Nov
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.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI
The price is SAR 2,135 per night from Dec 1 to Dec 2
SAR 2,135
SAR 2,740 total
includes taxes & fees
1 Dec - 2 Dec
9.2/10 Wonderful! (999 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?
You can find a variety of pricing options for a 5-star hotel in Upcountry Maui on Expedia. How much you’ll pay will depend on when you plan to travel, length of your trip and other factors. Compare all of the available properties for your desired dates and make use of our pricing and other filters to land the perfect upscale stay.

  • Search for the lowest price per night from SAR 1,389

What makes a hotel 5 stars in Upcountry Maui?
From gourmet dining venues and all-day fitness centers to pools and superior bedding, the 5-star experience in Upcountry Maui is all about indulgence and comfort. But it requires more than just upscale perks to receive a 5-star rating. Hotels also have to provide outstanding guest-centric services like in-room massages, on-site dry cleaning and laundry and room service any time day or night.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Our filter tool is the best way to search for exactly what you’re looking for. Select “5-star” and “All inclusive” to see the most upscale properties in Upcountry Maui where your room, meals, activities and entertainment are included in the upfront price. At these getaways, your trip is pure leisure from the moment you put down your suitcase.
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 a memorable getaway. Find one that suits your needs by checking out our vacation rentals in Upcountry Maui.