Find 5 Star Hotels in Upcountry Maui, HI from SAR 1,103

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
23 Jul - 24 Jul
Tomorrow
24 Jul - 25 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

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

Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great hotel! Loved our stay."
The price is SAR 3,026
SAR 3,791 total
includes taxes & fees
11 Aug - 12 Aug
Fairmont Kea Lani Maui
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, (1002)
"Amazing stay and service. Four Seasons always exceeded our expectations. Beautiful resort with nice beaches and pools. Family loved it."
The price is SAR 3,432
SAR 4,049 total
includes taxes & fees
31 Jul - 1 Aug
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
9 outdoor pools, cabanas (surcharge), sun loungers

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
8.8 out of 10, Excellent, (1004)
"This place was AMAZING!!!"
The price is SAR 3,372
SAR 4,222 total
includes taxes & fees
1 Aug - 2 Aug
Grand Wailea Maui, A Waldorf Astoria Resort
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, (1007)
"Great location! Nice beach! Plenty of excellent dining options nearby! Staff is helpful and knowledgeable! "
The price is SAR 3,372
SAR 4,222 total
includes taxes & fees
25 Jul - 26 Jul
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, (1002)
"This place is truly amazing! The service is impeccable, the resort is beautiful, and the views are breathtaking. I can’t wait to return again."
The price is SAR 2,971
SAR 3,725 total
includes taxes & fees
2 Aug - 3 Aug
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, (201)
"Super nice "
The price is SAR 3,752
SAR 4,824 total
includes taxes & fees
21 Aug - 22 Aug
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, (42)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is SAR 7,650
SAR 9,267 total
includes taxes & fees
17 Aug - 18 Aug
Ho‘olei Villas at Grand Wailea
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, sun loungers

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (3)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
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, (5)
"It’s a decent hotel to stay for the family."
The price is SAR 8,224
SAR 9,922 total
includes taxes & fees
17 Aug - 18 Aug
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment | Private kitchen | Full-size fridge, microwave, oven, stovetop

Wailea Luxury Hilltop Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"very nice place and location 🤗"
Wailea Luxury Hilltop Resort Vistas
Oceanfront Kihei Paradise Vistas
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. "
Oceanfront Kihei Paradise Vistas
Centrally Located Elegant Vistas
Luxury Condo | Balcony

Centrally Located Elegant Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
"Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!"
Centrally Located Elegant Vistas
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort Vistas
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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 SAR 1,940 per night from Aug 23 to Aug 24
SAR 1,940
SAR 2,505 total
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (884 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.

Learn more about Upcountry Maui

Head to sights like Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also known for its island views.

See all hotels in Upcountry Maui
Maui Island featuring landscape views

Top Upcountry Maui Hotel Reviews

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

10/10 Excellent
"Great location! Nice beach! Plenty of excellent dining options nearby! Staff is helpful and knowledgeable! "
Christer 7-night trip
Posted 2 days ago
The Ritz-Carlton Maui, Kapalua

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 1,103

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.