A barren volcanic landscape with rugged terrain and distant mountains.

5 Star Hotels in Upcountry Maui, Hawaii

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Check availability on Upcountry Maui 5 Star Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Upcountry Maui 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,005 reviews)
"Beautiful hotel, great amenities, so many pools and fun things and beach access, restaurants, bar, will definitely go back!"
United States
Seyed Kamyar
The price is €790
includes taxes & fees
20 Nov - 21 Nov
Grand Wailea Maui, A Waldorf Astoria Resort
A resort with a large pool, palm trees, and a view of the ocean.

2. The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali
5.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,336 reviews)
"Clean, beautiful grounds, friendly staff, great location. Would stay again."
United States
Glen
The price is €673
includes taxes & fees
29 Nov - 30 Nov
The Westin Maui Resort & Spa, Ka'anapali
A staircase with a view of a garden, palm trees, and a bridge.

3. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,006 reviews)
"Great place to stay with the family."
United States
Iulian
The price is €1,126
includes taxes & fees
28 Nov - 29 Nov
Fairmont Kea Lani Maui
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

4. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,000 reviews)
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
United States
Quinn
The price is €1,096
includes taxes & fees
28 Nov - 29 Nov
Four Seasons Resort Maui at Wailea
A resort with a large pool, a water slide, and a view of the ocean.

5. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
5.0 star property
Wailea
9.0 out of 10, Wonderful, (1,002 reviews)
"Not sure if you can beat the pools, value, location, views, snorkel, and staff on the island! Loved our stay!"
United States
Rachel
The price is €643
includes taxes & fees
29 Nov - 30 Nov
Wailea Beach Resort - Marriott, Maui
A pool area with lounge chairs and palm trees, overlooking the ocean.

6. The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1,000 reviews)
"The property was beautiful. Staff were very attentive and went above and beyond to make our experience memorable. The restaurants on the property also had amazing food. Overall great experience."
United States
Melisa
The price is €1,020
includes taxes & fees
30 Oct - 31 Oct
The Ritz-Carlton Maui, Kapalua
A poolside area with a fire pit, lounge chairs, and umbrellas.

7. Hotel Wailea Maui

Hotel Wailea Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,003 reviews)
"Spacious and updates rooms with everything you need. The service is simply outstanding. The pool was never crowded. The food at the restaurants was so good!"
United States
Maureen
The price is €1,010
includes taxes & fees
1 Nov - 2 Nov
Hotel Wailea Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

8. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (54 reviews)
"The room was beautiful the view incredible , the amenities were perfect. I would stay again and again"
United States
Risa
The price is €1,992
includes taxes & fees
29 Nov - 30 Nov
Ho‘olei Villas at Grand Wailea
A resort with a swimming pool, lounge areas, and a view of the ocean.

9. The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (217 reviews)
"Very accommodating hotel with wonderful staff and amazing view. Gluten free also!"
United States
John
The price is €1,218
includes taxes & fees
29 Nov - 30 Nov
The Resort at Kapalua Bay, Maui
A resort with multiple bungalow-style buildings, a swimming pool, and a beach.

10. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
7.8 out of 10, Good, (27 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is €335
includes taxes & fees
9 Nov - 10 Nov
Royal Lahaina Bungalows & Spa
A spacious living room with a large window, a ceiling fan, a sofa, a coffee table, and a TV.

11. Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (3 reviews)
"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. "
United States
Mae
Oceanfront Kihei Paradise Vistas
A balcony with a wooden table, a bottle of champagne, and a flower arrangement.

12. 2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (11 reviews)
"Beautifully renovated. Everything you need to enjoy the beach is there for you to use."
United States
Carrie
2 2 Oceanview Modern Resort Vistas
A hotel courtyard with palm trees, outdoor seating, and a view of the ocean at sunset.

13. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
Villa, Garden View, 2-bedroom
A spacious balcony with a view of the ocean, furnished with a sofa, chairs, and a coffee table.

14. Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
10.0 out of 10, Exceptional, (1 review)
"Service was impeccable, they took care of our every need promptly and gracefully. Beautiful setting."
United States
Mariana
The price is €824
includes taxes & fees
31 Oct - 1 Nov
Kapalua Bay Villas Resort by KBM
A resort with a pool, outdoor seating, and a view of the ocean.

15. Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Condo was very well stocked and very clean. Thank you for great accommodations."
United States
Shirley
Aloha Chic Penthouse 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.
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

2780 Kekaa Dr Lahaina HI
The price is €259 per night from 30 Oct to 31 Oct
€259
30 Oct - 31 Oct
includes taxes & fees
8.6/10 Excellent! (1,951 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

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing city also notable for its island views.

See all hotels in Upcountry Maui
A barren volcanic landscape with rugged terrain and distant mountains.
Photo by Project Forever
Open Photo by Project Forever

Top Upcountry Maui Hotel Reviews

The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent
"Great location on Ka’anapali Beach area. Lots of restaurants and shops nearby."
Stephen 5-night trip
Posted less than an hour ago
The Westin Maui Resort & Spa, Ka'anapali

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 €259

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.

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