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5 Stars Hotels in Kaupakulua, Haiku from CA $590

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Check availability on Kaupakulua 5 Star Hotels

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Oct 4 - Oct 5
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Oct 9 - Oct 11
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Oct 16 - Oct 18

Our top choices for Kaupakulua 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.
An aerial view of a beach resort with rows of sun loungers, palm trees, and a view of the ocean.
A resort with multiple buildings, a beach, and a mountainous backdrop.
A resort with a pond, a wooden bridge, and lush greenery.

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
United States
Mary Ann
CA $1,081
CA $1,375 total
includes taxes & fees
Oct 25 - Oct 26
Grand Wailea Maui, A Waldorf Astoria Resort
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 bar area with a curved counter, multiple bar stools, and a view of palm trees and the ocean at dusk.
A resort with a pool, beach, and mountain view.

2. Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
Wailea
United States
Quinn
CA $1,461
CA $1,827 total
includes taxes & fees
Oct 19 - Oct 20
Four Seasons Resort Maui at Wailea
A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.
A spa setting with a bathtub, candles, flowers, and a champagne bottle.
A serene outdoor seating area with two tables covered in white tablecloths and wooden stools, overlooking a coastal view with the ocean and a distant island.
A well-maintained golf course with a clear view of the ocean and a winding path.

3. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
Wailea
United States
Christina
CA $837
CA $1,093 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 spacious lobby with a curved wooden arch, seating areas, and a bar.
A resort pool area with lounge chairs, umbrellas, and palm trees.
A balcony with a view of the ocean and sunset.

4. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
Wailea
United States
Blanca Veronica
CA $1,509
CA $1,891 total
includes taxes & fees
Oct 24 - Oct 25
Fairmont Kea Lani Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.
A bar area with a view of palm trees and the ocean at sunset.
A room with a view of the ocean and lush greenery.
A spacious indoor area with a high ceiling, large windows, and a view of the ocean.

5. Hotel Wailea Maui

Hotel Wailea Maui
Wailea
United States
Rashonner
CA $1,210
CA $1,521 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Wailea Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.
A multi-level hotel atrium with a central bar, outdoor seating, and multiple balconies.
A pool with a waterfall feature, lounge chairs, and palm trees under a sunset sky.
A golf course with a pond, trees, and a view of the ocean.

6. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
Wailea
United States
Justin Robert
CA $2,456
CA $3,008 total
includes taxes & fees
Oct 18 - Oct 19
Ho‘olei Villas at Grand Wailea
A staircase with a view of a garden, palm trees, and a bridge.
A resort with multiple buildings, a swimming pool, and a view of the ocean.
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.

7. Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
Wailea
United States
Sze Wai
CA $3,761
CA $4,564 total
includes taxes & fees
Oct 28 - Oct 29
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 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.
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.

8. 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 hotel with multiple balconies, a well-maintained lawn, and palm trees.
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 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.

9. 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.
Hiking
A golf course with a water body, trees, and a distant mountain.
A wooden bridge over a pond, a well-maintained lawn, and a building with a balcony.

10. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
Wailea
CA $1,224
CA $2,260 total
includes taxes & fees
Oct 7 - Oct 8
Villa, Garden View, 2-bedroom
A resort with a pool, outdoor seating, and a view of the ocean.
A modern living room with a large TV, a dining area, and a kitchen.
A modern kitchen with a built-in microwave, a dining area with wooden chairs, and a large window offering a view.
A modern kitchen with a large island, stainless steel appliances, and bar stools.

11. Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
Central Kihei
United States
Shirley
Aloha Chic Penthouse Vistas
A modern kitchen with white cabinets, stainless steel appliances, and a large island.
A clear swimming pool with a wooden deck and lounge chairs around it, surrounded by lush greenery.
A modern kitchen with white cabinets, a large marble island, stainless steel appliances, and wicker pendant lights.
A kitchen with a large window offering a view of a tropical landscape, a coffee maker, and a sink.

12. Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
Wailea
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
A modern living room with a large TV, comfortable seating, and a view of the ocean through sliding glass doors.
A modern kitchen with grey cabinets, stainless steel appliances, and a white marble countertop.
A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a living room with a sofa and coffee table.
A kitchen counter with a coffee maker, a bag of cookies, a bottle of beer, and a decorative card.

13. Upscale Luxurious Ocean Resort Vistas

Upscale Luxurious Ocean Resort Vistas
South Kihei
Upscale Luxurious Ocean Resort Vistas
A modern living room with a large TV, comfortable seating, and a balcony with a view of buildings and greenery.
A modern kitchen with a central island, pendant lighting, and a ceiling fan.
A modern living room with a sofa, coffee table, and a large TV displaying a beach scene.
A kitchen counter with a bottle of Pellegrino water, a box of Mini Bites Lemon, and a potted orchid.

14. Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
South Kihei
United States
Edwin
Centrally Located Elegant 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
CA $1,049
CA $1,329 total
Nov 5 - Nov 6
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Andaz Maui at Wailea Resort - a concept by Hyatt
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

88 WAILEA IKE PLACE Kihei HI
CA $640
CA $802 total
Oct 20 - Oct 21
includes taxes & fees
AC Hotel by Marriott Maui Wailea
Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

575 S Kihei Road Kihei HI
CA $455
CA $590 total
Oct 17 - Oct 18
includes taxes & fees
9.4/10 Exceptional! (406 reviews)
Hilton Grand Vacations Club Maui Bay Villas
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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

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"If you’re thinking of going to Maui for your honeymoon- think the Wailea Beach Resort by Marriott. You’ll be happy you did. Truly an amazing resort with unbeatable sunset and ocean views. Shay at the Adult Pool is absolutely amazing!!"
Marielle 4-night trip
Posted 1 day ago
Wailea Beach Resort - Marriott, Maui
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
Quinn 5-night trip
Posted 1 day ago
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"We had a wonderful visit"
Mary Ann 7-night trip
Posted 1 day ago
Grand Wailea Maui, A Waldorf Astoria Resort

Find out more about Kaupakulua

Five Star Hotels in Kaupakulua

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Kaupakulua so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Kaupakulua and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Kaupakulua

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Kaupakulua

The results are in, and Kaupakulua 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Kaupakulua! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Kaupakulua today and settle down in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Kaupakulua?
There are a range of pricing options for a 5-star hotel in Kaupakulua on Expedia. How much you'll pay will depend on your vacation dates, length of your trip and other factors. Compare available properties for your chosen dates and use our pricing and other filters to score the perfect high-end stay.
  • Search for the lowest price per night from CA $590
What makes a hotel 5 stars in Kaupakulua?
From high-end restaurants and all-day gyms to swimming pools and premium bedding, the 5-star experience in Kaupakulua is all about relaxation and luxury. But it calls for more than just upscale perks to receive a 5-star rating. Stays also have to offer remarkable services like in-room massage treatments, on-site dry cleaning and laundry and 24-hour room service.
Are there any 5-star all-inclusive resorts in Kaupakulua?
Use Expedia's filters to find a luxurious getaway in Kaupakulua where everything you need is included. Next, narrow down your results for properties that have 5 stars and are deemed "All inclusive." The most important thing to look forward to at these stays? Pure indulgence and relaxation.

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