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5 Stars Hotels in Olowalu, Hawaii from CA $489

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Our top choices for Olowalu 5-star hotels

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,002 reviews)
"Súper friendly staff. Amazing property. Awesome suites."
United States
Kelly Ramos
The price is CA $1,283
CA $1,606 total
includes taxes & fees
Aug 21 - Aug 22
Fairmont Kea Lani Maui

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, (1,000 reviews)
"Beautiful property, amazing pools and wonderful service."
United States
Ashley
The price is CA $1,217
CA $1,537 total
includes taxes & fees
Aug 9 - Aug 10
Grand Wailea Maui, A Waldorf Astoria Resort

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1,000 reviews)
"Our stay was wonderful, "
United States
Christopher
The price is CA $1,127
CA $1,437 total
includes taxes & fees
Jul 31 - Aug 1
The Ritz-Carlton Maui, Kapalua

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,000 reviews)
"Excellent staff and service!"
Canada
Ifelere
The price is CA $1,552
CA $1,935 total
includes taxes & fees
Aug 22 - Aug 23
Four Seasons Resort Maui at Wailea

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,000 reviews)
"The property was beautiful and well maintained. Lush garden spaces. Pool area and loungers being available along with poolside service was great. Room was large and felt very private. Overall quiet property and relaxing stay. Beach picnic excursion was great as well!"
United States
Mitchell
The price is CA $992
CA $1,262 total
includes taxes & fees
Aug 2 - Aug 3
Hotel Wailea, Relais & Chateaux - Adults Only

Four Seasons Resort Lanai

Four Seasons Resort Lanai
5.0 star property
Lanai City
9.8 out of 10, Exceptional, (230 reviews)
"Great room, great food "
United States
Joseph
The price is CA $1,693
CA $2,010 total
includes taxes & fees
Jul 23 - Jul 24
Four Seasons Resort Lanai

Sensei Lanai, A Four Seasons Resort

Sensei Lanai, A Four Seasons Resort
5.0 star property
Lanai City
9.8 out of 10, Exceptional, (148 reviews)
"The spa was the best one I have ever been to. Great amenities, and gorgeous place overall. The staff was incredibly kind. Would love to be back"
United States
Andrea
Sensei Lanai, A Four Seasons Resort

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (49 reviews)
"Overall, our stay at Ho’olei was wonderful, as always! We were a party of eight, and the three-bedroom villa was the perfect setup for our family. There was something for everyone to enjoy, especially the kids. We loved the fitness classes, the pools on both sides of the property, the dining options, and the Fourth of July festivities. The villa was spotless, spacious, and very comfortable. One of our favorite parts of the trip was enjoying dinner on the lanai while watching the beautiful...
Canada
Stephanie
The price is CA $2,441
CA $2,990 total
includes taxes & fees
Aug 21 - Aug 22
Ho‘olei Villas at Grand Wailea

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
7.8 out of 10, Good, (20 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is CA $542
CA $718 total
includes taxes & fees
Aug 18 - Aug 19
Royal Lahaina Bungalows & Spa

The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (215 reviews)
"Loved the pool layout and the gorgeous ocean view. Not noisy, very minimal music played at the pool which was nice! The snorkeling on site is better than Molokini crater. The only slight downside is that the beach is a bit small and there were limited restaurants on site but that is only a tiny negative. Loved this resort and would come back."
United States
Nathalie
The price is CA $1,801
CA $2,447 total
includes taxes & fees
Aug 22 - Aug 23
The Resort at Kapalua Bay, Maui

Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Condo was very well stocked and very clean. Thank you for great accommodations."
United States
Shirley
Aloha Chic Penthouse Vistas

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

2 2 Oceanview Modern Resort Vistas

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

Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
10.0 out of 10, Exceptional, (1 review)
"Service was impeccable, they took care of our every need promptly and gracefully. Beautiful setting."
United States
Mariana
Kapalua Bay Villas Resort by KBM

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 CA $4,655
CA $5,609 total
includes taxes & fees
Aug 19 - Aug 20
Fairmont Kea Lani Maui Villa Experience

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (3 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

Hale Ona Loa HOL-102 by KBM

Hale Ona Loa HOL-102 by KBM
5.0 star property
Kaanapali
The price is CA $809
CA $1,650 total
includes taxes & fees
Aug 19 - Aug 20
Hale Ona Loa HOL-102 by KBM

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

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

Upscale Luxurious Ocean Resort Vistas

Upscale Luxurious Ocean Resort Vistas
5.0 star property
South Kihei
Upscale Luxurious Ocean Resort Vistas
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Learn more about Olowalu

Trip time! Discover the local cuisine and beaches in romantic Olowalu.

A person relaxing on a beach under a tree with a view of the sea and distant mountains.
Photo by Rachel Elyse
Open Photo by Rachel Elyse

Top Olowalu Hotel Reviews

Find out more about Olowalu

Five Star Hotels in Olowalu

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 Olowalu 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 Olowalu and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Olowalu

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 Olowalu

The results are in, and Olowalu 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 Olowalu! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Olowalu 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 Olowalu?
There are a range of pricing options for 5-star hotels in Olowalu on Expedia. How much you'll pay will depend on when you plan to travel, length of stay and other factors. Compare all of the available properties for your chosen dates and use our pricing and other filters to find the perfect upscale stay.

  • Search for the lowest price per night from CA $489

What makes a hotel 5 stars in Olowalu?
In Olowalu, a hotel must provide a specific level of high-end conveniences to be designated 5 stars. These may include gourmet restaurants, saunas and spas, on-site gyms, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their superior service. You'll enjoy things like concierge services, in-room massages and nightly turn-down services. Some may also offer special touches such as a welcome gift.
Are there any 5-star all-inclusive resorts in Olowalu?
Expedia's filter tool is the easiest way to find exactly what you want. Check the "All inclusive" and "5-star" boxes to show the most luxurious resorts in Olowalu where your accommodations, meals, entertainment and activities are included in the price. At these getaways, your trip is pure leisure from the moment you pull up to the entrance.

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