A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Upcountry Maui 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.
A spacious balcony with a view of a pool and palm trees, furnished with wicker chairs and a coffee table.
A resort with a pond, a wooden bridge, and lush greenery.
An aerial view of a beach resort with rows of sun loungers, palm trees, and a view of the ocean.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
United States
Jason
NT$25,570
NT$32,415 total
includes taxes & fees
Oct 9 - Oct 10
Grand Wailea Maui, A Waldorf Astoria Resort
A resort with a large pool, palm trees, and a view of the ocean.
A gazebo with white columns and a metal roof, surrounded by lush tropical plants and a small water feature.
A beach with palm trees and a rainbow over the ocean.
A woman in a swimsuit standing by a pool with a view of the ocean and palm trees.

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

The Westin Maui Resort & Spa, Ka'anapali
Kannapali Beach Area
United States
Eugene
NT$14,449
NT$18,988 total
includes taxes & fees
Sep 28 - Sep 29
The Westin Maui Resort & Spa, Ka'anapali
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.
An aerial view of a resort with multiple pools, palm trees, and lounge areas.
A balcony with wicker furniture, a view of the ocean, palm trees, and a mountain in the distance.
A resort with a pool, beach, and mountain view.

3. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
Wailea
United States
You Jin
NT$26,198
NT$33,173 total
includes taxes & fees
Sep 28 - Sep 29
Four Seasons Resort Maui at Wailea
A pool area with lounge chairs and palm trees, overlooking the ocean.
An outdoor dining area with tables and chairs, palm trees, and string lights against a backdrop of the ocean and sky.
A covered outdoor seating area with a fire pit, overlooking a pool and lush greenery.
An aerial view of a coastal area with a sandy beach, clear turquoise waters, and dense green forest.

4. The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
Kapalua
United States
TAMIKA
NT$25,372
NT$32,344 total
includes taxes & fees
Oct 16 - Oct 17
The Ritz-Carlton Maui, Kapalua
A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.
A well-maintained golf course with a clear view of the ocean and a winding path.
A deck with two lounge chairs facing a scenic ocean view, a wooden floor, and a modern architectural design.
A spa setting with a bathtub, candles, flowers, and a champagne bottle.

5. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
Wailea
United States
Amalia
NT$19,148
NT$24,955 total
includes taxes & fees
Oct 25 - Oct 26
Wailea Beach Resort - Marriott, Maui
A staircase with a view of a garden, palm trees, and a bridge.
A balcony with a view of the ocean and sunset.
A spacious lobby with a curved wooden arch, seating areas, and a bar.
A resort with a large swimming pool, palm trees, and a view of the ocean.

6. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
Wailea
United States
Blanca Veronica
NT$31,798
NT$39,978 total
includes taxes & fees
Sep 27 - Sep 28
Fairmont Kea Lani Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.
A room with a view of the ocean and lush greenery.
A resort with a pool, a covered outdoor area, and a stone wall.
A spacious indoor area with a high ceiling, large windows, and a view of the ocean.

7. Hotel Wailea Maui

Hotel Wailea Maui
Wailea
United States
Rashonner
NT$28,548
NT$35,775 total
includes taxes & fees
Sep 27 - Sep 28
Hotel Wailea Maui
A spacious living area with a high ceiling, a dining set, and a sofa facing a large window overlooking the ocean at sunset.
A coastal golf course with a view of the ocean, a clear sky, and a golfer on the green.
A resort with multiple buildings, a swimming pool, and a beachfront.
A living room with a sofa, chairs, a coffee table, and a view of the ocean.

8. The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
Lahaina
United States
Nathalie
NT$32,993
NT$46,141 total
includes taxes & fees
Oct 10 - Oct 11
The Resort at Kapalua Bay, Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.
A spacious kitchen with a large island, wooden cabinets, and a view of the ocean.
A multi-level hotel atrium with a central bar, outdoor seating, and multiple balconies.
A golf course with a pond, trees, and a view of the ocean.

9. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
Wailea
United States
Justin Robert
NT$54,656
NT$66,944 total
includes taxes & fees
Oct 10 - Oct 11
Ho‘olei Villas at Grand Wailea
A resort with multiple bungalow-style buildings, a swimming pool, and a beach.
A resort with a beach, a swimming pool, and a large building.
A hotel room with a large bed, a desk with a chair, a view of the ocean, and a balcony with a hanging light fixture.
A beachfront property with a large tree, a well-maintained lawn, and a view of the ocean.

10. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
Lahaina
United States
AURA MARINA
NT$10,797
NT$14,513 total
includes taxes & fees
Sep 27 - Sep 28
Royal Lahaina Bungalows & Spa
A staircase with a view of a garden, palm trees, and a bridge.
A spacious outdoor lounge area with multiple seating options, including sofas and chairs, surrounded by lush greenery and architectural features like arches and a pergola.
A resort with multiple swimming pools, palm trees, and a view of the ocean.
A resort with multiple buildings, a swimming pool, and a view of the ocean.

11. Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
Wailea
United States
Sze Wai
NT$82,531
NT$100,199 total
includes taxes & fees
Oct 22 - Oct 23
Fairmont Kea Lani Maui Villa Experience
A spacious living room with a large window, a ceiling fan, a sofa, a coffee table, and a TV.
A room with a blue cabinet, a mirror, and a plant.
A modern living room with a wicker chair, a blue sofa, and a dining area in the background.
A modern living room with a wooden coffee table, a sofa with blue cushions, a dining area with wicker chairs, and a kitchen with a refrigerator.

12. Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
Central Kihei
United States
Mae
Oceanfront Kihei Paradise Vistas
A balcony with a wooden table, a bottle of champagne, and a flower arrangement.
A modern kitchen with grey cabinets, a built-in oven, and a white countertop. There is a dining area with a wooden table and blue chairs.
A kitchen with a microwave, a knife block, a bottle of Veuve Clicquot champagne, and two glasses on a marble countertop.
A living room with a blue sofa, a coffee table, and a TV on the wall. There is a balcony with a view of the ocean and palm trees.

13. 2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
Central Kihei
United States
Carrie
2 2 Oceanview Modern Resort Vistas
A resort pool area with a hot tub, lounge chairs, and palm trees.
A golf course with a water body, trees, and a distant mountain.
A resort with a swimming pool, palm trees, and a mountainous backdrop.

14. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
Wailea
NT$17,627
NT$38,907 total
includes taxes & fees
Oct 6 - Oct 7
Villa, Garden View, 2-bedroom
A room with a large glass door leading to a balcony with a view of the ocean and palm trees.
A spacious living area with a view of the ocean, a dining area, and a kitchen.
A spacious living area with a large window overlooking the ocean, a ceiling fan, and a wooden floor.
A modern kitchen with a large island, a glass top stove, and a view of the ocean.

15. Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
Kapalua
United States
Mariana
NT$15,938
NT$34,525 total
includes taxes & fees
Oct 13 - Oct 14
Kapalua Bay Villas Resort by KBM
A resort with a pool, outdoor seating, and a view of the ocean.
A modern kitchen with a large island, stainless steel appliances, and bar stools.
A hotel with multiple balconies, a swimming pool area, and palm trees.
A modern kitchen with a built-in microwave, a dining area with wooden chairs, and a large window offering a view.

16. Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
Central Kihei
United States
Shirley
Aloha Chic Penthouse Vistas
A rooftop terrace with a view of the ocean, palm trees, and outdoor seating.
A living room with a sofa, coffee table, TV, and a ceiling fan.
A modern living room with a sofa, coffee table, and a decorative lamp.

17. Hale Ona Loa HOL-102 by KBM

Hale Ona Loa HOL-102 by KBM
Kaanapali
NT$8,879
NT$26,146 total
includes taxes & fees
Oct 5 - Oct 6
Hale Ona Loa HOL-102 by KBM
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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
NT$15,004
NT$19,508 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (1,873 reviews)
Royal Lahaina Resort & Bungalows
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

200 Nohea Kai Dr Lahaina HI
NT$14,455
NT$19,007 total
Sep 28 - Sep 29
includes taxes & fees
Hyatt Regency Maui Resort & Spa
Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

2605 Kaanapali Pkwy Lahaina HI
NT$12,162
NT$16,273 total
Oct 14 - Oct 15
includes taxes & fees
Sheraton Maui Resort & Spa
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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 area also known for its island views.

See all hotels in Upcountry Maui
A barren volcanic landscape with rugged terrain and distant mountains.
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
"Clean rooms"
Ingrid Viviana Perez 5-night trip
Posted 6 hours ago
The Westin Maui Resort & Spa, Ka'anapali
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

10/10 Excellent
"Our first stay in Wailea and we felt welcome from the very first moment we pulled into the resort. Amazing and friendly staff in a luxury setting. Plenty of lounge chairs with full towel covers. The beach path is great as well. A truly relaxing holiday. We hope to return."
Gabriel 3-night trip
Posted 11 hours ago
Fairmont Kea Lani Maui
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

10/10 Excellent
"👍"
Ella 7-night trip
Posted 1 day ago
The Ritz-Carlton Maui, Kapalua
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"Incredible service and high end property. The rooms are updated with a nice balcony. 3 pools and direct beach access makes it easy."
Alon 6-night trip
Posted 1 day ago
Four Seasons Resort Maui at Wailea
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"I loved the cleanliness of the hotel as well as the exceptional staff. Everyone was so polite and welcoming."
Tiffany 17-night trip
Posted 2 days ago
Wailea Beach Resort - Marriott, Maui
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

8/10 Good
"Swim up bar was over crowded"
James 5-night trip
Posted 3 days ago
Grand Wailea Maui, A Waldorf Astoria Resort

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$16,273
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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