Upcountry Maui 5 Stars Hotels

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19

Top Upcountry Maui 5 Stars Hotels

Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Loved the resort very well kept & beautiful spa was the best too"
The price is P54,340
P67,514 total
includes taxes & fees
Nov 1 - Nov 2
Fairmont Kea Lani Maui
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, (1000)
"Stunning resort!"
The price is P37,444
P47,925 total
includes taxes & fees
Oct 21 - Oct 22
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, (1005)
"This hotel is "
The price is P47,974
P60,346 total
includes taxes & fees
Oct 12 - Oct 13
The Ritz-Carlton Maui, Kapalua
Four Seasons Resort Maui at Wailea
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, (1001)
"Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again. "
The price is P43,692
P51,540 total
includes taxes & fees
Oct 26 - Oct 27
Four Seasons Resort Maui at Wailea
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, (1001)
"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! "
The price is P54,640
P67,868 total
includes taxes & fees
Nov 4 - Nov 5
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, (202)
"Super nice "
The price is P57,870
P74,408 total
includes taxes & fees
Oct 27 - Oct 28
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, (43)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is P118,489
P143,526 total
includes taxes & fees
Oct 12 - Oct 13
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
View from property

Fairmont Kea Lani Maui Villa Experience

5.0 star property
9.8 out of 10, Exceptional, (6)
"It’s a decent hotel to stay for the family."
The price is P164,872
P197,883 total
includes taxes & fees
Oct 6 - Oct 7
Fairmont Kea Lani Maui Villa Experience
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, (4)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
Wailea Luxury Hilltop Resort Vistas
Private kitchen

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
Centrally Located Elegant Vistas
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
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
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort Vistas
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
Property entrance

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
Pool

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
View from room

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay
Terrace/patio

KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay

5.0 star property
KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
Pool

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

5.0 star property
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616
View from room

NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616

5.0 star property
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei, HI
The price is P45,659 per night from Nov 2 to Nov 3
P45,659
P57,258 total
Nov 2 - Nov 3
includes taxes & fees
9.2/10 Wonderful! (997 reviews)
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.
PoolSpaHot tubBreakfast includedWaterpark
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 showing landscape views

Top Upcountry Maui Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"Beautiful property, efficient staff, truly a wonderful stay "
Angela 5-night trip
Posted 1 day ago
Four Seasons Resort Maui at Wailea

Find out more about Upcountry Maui

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 P17,226

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia