Explore top 2026 5 Star Hotels in Olowalu

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Top Olowalu 5 Star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$850 nightly
The price is $1,009 total per night from Feb 11 to Feb 12
$1,009 total
Feb 11 - Feb 12
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and ...
9.6/10 Exceptional! (1,001 reviews)
Great staff and service

Reviewed on Jan 18, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$763 nightly
The price is $905 total per night from Feb 8 to Feb 9
$905 total
Feb 8 - Feb 9
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers ...
8.8/10 Excellent! (1,003 reviews)
The staff was wonderful as we spend the day at the pool. Easy to order food and drinks. Lots of good choices. Towels were easy to get and return.

Reviewed on Jan 20, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,035 nightly
The price is $1,229 total per night from Jan 31 to Feb 1
$1,229 total
Jan 31 - Feb 1
Total with taxes and fees
A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's ...
9.4/10 Exceptional! (1,006 reviews)
All around amazing experience. Gorgeous setting, great amenities, our trip went off without a hitch.

Reviewed on Jan 23, 2026

Opens in a new windowFairmont Kea Lani Maui
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive Kapalua HI
$954 nightly
The price is $1,132 total per night from Jan 26 to Jan 27
$1,132 total
Jan 26 - Jan 27
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 6 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. There's ...
9/10 Wonderful! (1,000 reviews)
Yes it's secluded. Yes it is a large property that requires a lot of walking. The rooms are slightly dated. It's all made up by the attention and care from the staff at the Ritz. My wife and I were celebrating our honeymoon. We were treated with the utmost care from the kind folks there. The property ...

Reviewed on Jan 3, 2026

Opens in a new windowThe Ritz-Carlton Maui, Kapalua
Four Seasons Resort Lanai

Four Seasons Resort Lanai

5 out of 5
1 Manele Bay Road Lanai City HI
$1,200 nightly
The price is $1,425 total per night from Jan 27 to Jan 28
$1,425 total
Jan 27 - Jan 28
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 7 restaurants. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
9.6/10 Exceptional! (223 reviews)
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Reviewed on Nov 9, 2025

Opens in a new windowFour Seasons Resort Lanai
Sensei Lanai, A Four Seasons Resort

Sensei Lanai, A Four Seasons Resort

5 out of 5
1 Keomoku Hwy Lanai City HI
A golf course, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, ...
9.6/10 Exceptional! (137 reviews)
Transformative experience! Highly recommended - unlike any other vacation!

Reviewed on Aug 18, 2025

Opens in a new windowSensei Lanai, A Four Seasons Resort
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
$1,039 nightly
The price is $1,234 total per night from Jan 31 to Feb 1
$1,234 total
Jan 31 - Feb 1
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...
9.2/10 Wonderful! (1,002 reviews)
Rooms are beautiful

Reviewed on Jan 13, 2026

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
One Bay Drive Lahaina HI
$1,630 nightly
The price is $1,964 total per night from Feb 14 to Feb 15
$1,964 total
Feb 14 - Feb 15
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. There's fun for all ages with a children's club and a children's ...
9.6/10 Exceptional! (205 reviews)
Super nice

Reviewed on Jun 16, 2025

Opens in a new windowMontage Kapalua Bay
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
$2,128 nightly
The price is $2,527 total per night from Feb 9 to Feb 10
$2,527 total
Feb 9 - Feb 10
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...
9.6/10 Exceptional! (43 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.

Reviewed on Jun 15, 2025

Opens in a new windowHo‘olei Villas at Grand Wailea
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
2780 Kekaa Drive Lahaina HI
Fully refundableReserve now, pay when you stay
$525 nightly
The price is $623 total per night from Jan 26 to Jan 27
$623 total
Jan 26 - Jan 27
Total with taxes and fees
A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are all featured at this luxury aparthotel. Enjoy beachfront dining and relax with beach cabanas ...
9.4/10 Exceptional! (3 reviews)
Everything was amazing

Reviewed on Jan 5, 2026

Opens in a new windowRoyal Lahaina Bungalows & Spa
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Olowalu Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Olowalu to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Olowalu 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Olowalu before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Olowalu hotel reviews by fellow wanderers