Compare and book 5 Star hotels in Kaupakulua, Haiku

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Check availability on Kaupakulua 5 Star Hotels

Tonight
26 Jun - 27 Jun
Tomorrow
27 Jun - 28 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Kaupakulua 5 Star Hotels

Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1001)
"One of the best resorts in Hawaii "
The price is 19.481.005 ₫
22.980.183 ₫ total
includes taxes & fees
14 Jul - 15 Jul
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1002)
"We had the best time! The property is absolutely gorgeous and the weather was perfect. "
The price is 25.076.891 ₫
31.019.513 ₫ total
includes taxes & fees
14 Jul - 15 Jul
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1000)
"Great place for family."
The price is 21.093.091 ₫
26.424.100 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Fairmont Kea Lani Maui
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)
"This place is truly amazing! The service is impeccable, the resort is beautiful, and the views are breathtaking. I can’t wait to return again."
The price is 19.663.704 ₫
24.737.967 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Hotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea
Outdoor pool, pool loungers

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (42)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is 75.023.050 ₫
90.195.223 ₫ total
includes taxes & fees
10 Jul - 11 Jul
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
9.6 out of 10, Exceptional, (5)
"It’s a decent hotel to stay for the family."
The price is 88.884.373 ₫
106.384.992 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment | Private kitchen | Full-sized fridge, microwave, oven, stovetop

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
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, pool loungers

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
Oceanfront Kihei Paradise Vistas
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, pool loungers

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
Oceanfront Kihei Paradise Vistas
Centrally Located Elegant Vistas
Luxury Condo | 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
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic Area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort 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 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 19.219.515 ₫ per night from 25 Jul to 26 Jul
19.219.515 ₫
24.206.931 ₫ total
25 Jul - 26 Jul
includes taxes & fees
9.2/10 Wonderful! (997 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 Kaupakulua

Head to Haiku Park and Twin Falls—just two of the sights around Kaupakulua.

See all hotels in Kaupakulua

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 10.433.451 ₫

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.