Upcountry Maui 5 Stars Hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

Next weekend
In two weeks

Our top choices for Upcountry Maui 5-star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1001)
"Beautiful property, efficient staff, truly a wonderful stay "
Canada
Angela
The price is P46,795
P55,552 total
includes taxes & fees
Jan 13 - Jan 14
Four Seasons Resort Maui at Wailea

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, (1008)
"Very nice resort for a family vacation!"
United States
Ashwini
The price is P40,319
P51,682 total
includes taxes & fees
Jan 21 - Jan 22
Grand Wailea Maui, A Waldorf Astoria Resort

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1005)
"Wonderful staff and facility"
United States
Sheila
The price is P55,486
P69,363 total
includes taxes & fees
Jan 9 - Jan 10
Fairmont Kea Lani Maui

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.0 out of 10, Wonderful, (1002)
"Top notch property with amazing service and staff"
Canada
Delaine
The price is P47,031
P59,650 total
includes taxes & fees
Jan 6 - Jan 7
The Ritz-Carlton Maui, Kapalua

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1004)
"Staff was great and the property was stunning. It was everything we wanted for our honeymoon. Other couples mentioned "
United States
Jacob
The price is P58,803
P73,300 total
includes taxes & fees
Jan 6 - Jan 7
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

Montage Kapalua Bay
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (204)
"We used Spa, expedia mentioned there is 20% discount and we didn't get it"
United States
Ronak
The price is P65,043
P84,162 total
includes taxes & fees
Feb 4 - Feb 5
Montage Kapalua Bay

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (44)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
United States
Leslie
The price is P117,710
P143,554 total
includes taxes & fees
Feb 5 - Feb 6
Ho‘olei Villas at Grand Wailea

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.0 out of 10, Wonderful, (2)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is P24,487
P32,193 total
includes taxes & fees
Jan 7 - Jan 8
Royal Lahaina Bungalows & Spa

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is P170,061
P204,063 total
includes taxes & fees
Jan 12 - Jan 13
Fairmont Kea Lani Maui Villa Experience

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.8 out of 10, Exceptional, (7)
"The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! "
United States
Paulina
2 2 Oceanview Modern Resort Vistas

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
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. "
United States
Mae
Oceanfront Kihei Paradise Vistas

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
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!"
United States
Edwin
Centrally Located Elegant Vistas

KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203

KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203
5.0 star property
Kapalua
KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203

Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)

Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)

NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302

NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302
5.0 star property
Kapalua
NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)

Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)

Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)

Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
5.0 star property
Kaanapali
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)

Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436

Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436
5.0 star property
Kaanapali
Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436
Save an average of 15% on thousands of hotels when you're signed in

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.
Still don't see what you're looking for?
See all properties in Upcountry Maui.
You can also use these popular filters to refine your search.
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.

View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds.
#AboveItAll
Photo by Project Forever
Open Photo by Project Forever

Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Stay in Luxury: 5 Star Hotels in Upcountry Maui

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Upcountry Maui trip. You'll join the multitudes of holidaymakers who have made Upcountry Maui so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Upcountry Maui and indulge in the finer things in life for a while.

5-Star Hotels in Upcountry Maui

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Upcountry Maui are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Upcountry Maui 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Upcountry Maui! Choose one of our Upcountry Maui 5-star hotels today and soothe yourself in luxe surroundings at your convenience.


Expedia India is rated 4 stars by Feefo based on 1038 reviews

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 P27,906

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.