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Check availability on Kaupakulua 5 Star Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

Our top choices for Kaupakulua 5-star hotels

9 outdoor pools, pool cabanas (surcharge), pool loungers

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, (1,006 reviews)
"Great hotel. Had an awesome stay and staff was very friendly. Beautiful property and love that you could walk right onto the beach from the resort."
United States
Dustin
The price is 21.327.543 ₫
27.026.578 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Grand Wailea Maui, A Waldorf Astoria Resort
Property grounds

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,002 reviews)
"Wonderful Hotel Great restaurants staffed by true professionals "
United States
John
The price is 24.875.235 ₫
31.248.518 ₫ total
includes taxes & fees
16 Jul - 17 Jul
Four Seasons Resort Maui at Wailea
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,002 reviews)
"The resort was excellent and made for a great trip!"
United States
Ed
The price is 28.935.571 ₫
35.912.884 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Fairmont Kea Lani Maui
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,002 reviews)
"We had a good time. Comfortable hotel. "
United States
andrea
The price is 21.032.077 ₫
26.530.133 ₫ total
includes taxes & fees
12 Jul - 13 Jul
Hotel Wailea, Relais & Chateaux - Adults Only
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (48 reviews)
"Womderful home, terrific service, access to hotel amenities was key."
United States
ALAN
The price is 56.111.838 ₫
68.319.712 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Ho‘olei Villas at Grand Wailea
Balcony

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.8 out of 10, Exceptional, (9 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
View from property

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is 118.427.177 ₫
142.132.618 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Fairmont Kea Lani Maui Villa Experience
Luxury Apartment, Ocean View | Living area | Hulu, streaming services

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (2 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
BBQ/picnic Area

Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (4 reviews)
"Condo was very well stocked and very clean. Thank you for great accommodations."
United States
Shirley
Aloha Chic Penthouse Vistas
Luxury Condo | Living area | 90-inch Smart TV with digital channels, Hulu, streaming services

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"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
Luxury Apartment | Beach/ocean view

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Living area | 700-inch Smart TV with cable channels, pay films

Upscale Luxurious Ocean Resort Vistas

Upscale Luxurious Ocean Resort Vistas
5.0 star property
South Kihei
Upscale Luxurious Ocean Resort Vistas
Shopping centre

NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts
5.0 star property
Wailea
NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts
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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 Kaupakulua.
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 20.096.926 ₫ per night from 24 Jul to 25 Jul
20.096.926 ₫
25.410.347 ₫ total
24 Jul - 25 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 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.

Top Kaupakulua Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

8/10 Good
"Overall a really nice stay at the Wailea. Our room got upgraded to a fantastic ocean view room in the Chapel wing. The pools were fantastic and so much fun with all the water slides. We would always arrive mid to late morning.  The breakfast buffet was not as good as I had hoped. All the baked items (pancakes, waffles, pastries, etc.) were super underwhelming and didn't feel fresh.  One thing really bothered me that I'm having trouble letting go of it. I ordered two drinks at the pool bar. When I went back to order a third the bartender told me he lost my first receipt and asked me to sign a new receipt for a charge of 3 drinks. I did however when I asked to confirm that the first charge would not appear on my bill I wasn't totally confident in his answer. So I texted the front desk to ensure I wasn't being double charged. It took them 28 hours from my first test to get back to me with an answer. This caused me extra anxiety and worry during one of my vacation days that felt so unnecessary and really stained the service of the hotel. All over a $75 drink order.... I don't understand why they couldn't get an answer to me sooner and never really got an explanation. The last thing is they have no place to shower off after check out for those who fly out later. We had a red eye and stayed at the hotel way beyond checkout time. I had to fly home covered in sand and chlorine. My husband used soap in the beach showers to get as clean as possible."
Blair 3-night trip
Posted 2 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 Kaupakulua?
How much you pay for a 5-star hotel in Kaupakulua depends on things such as when you want to go and the length of your holiday. An insider tip for bagging the best deal? Use our pricing filters to compare all of the available accommodation for your selected dates.

  • Search for the lowest price per night from 13.399.745 ₫

What makes a hotel 5 stars in Kaupakulua?
Exceptional guest service is integral to every 5-star hotel in Kaupakulua. From the instant you arrive, staff cater to your every whim, whether offering luggage assistance and storage or providing a nightly turn-down service. Also, hotels must offer upscale conveniences to be eligible for a 5-star rating. These can include luxury toiletries, spas or saunas, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Kaupakulua?
Use Expedia's filter tool to find a high-end getaway in Kaupakulua where most of what you need is included in the price. After your initial search, narrow down your results for resorts that have a 5-star rating and are listed as "All inclusive." The main thing on the itinerary at these stays? Relaxation and indulgence.