Explore top 2026 5 Star Hotels in Olowalu
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Olowalu 5 Star hotels
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
$765 nightly
The price is $908 total per night from Apr 30 to May 1
$908 total
Apr 30 - May 1
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)
Last night on an extended trip to Asia, stopped over in Maui. A perfect end to our trip (despite the inclement weather). We have always stayed in the Ka'anapali area of Maui, but due to weather Wailea was better option for this trip and The Four Seasons didn't disappoint. Would definitely consider ...
Reviewed on Mar 28, 2026
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
$1,149 nightly
The price is $1,364 total per night from Apr 17 to Apr 18
$1,364 total
Apr 17 - Apr 18
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! (1,002 reviews)
nice hotel but not amazing would say the pool and amenities felt lacking. Pretty expensive for what it is
Reviewed on Apr 4, 2026
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
$716 nightly
The price is $850 total per night from May 6 to May 7
$850 total
May 6 - May 7
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! (1,007 reviews)
Absolutely terrible. I had to wake up every morning and line up at 6:15 am to get pool chairs. The hotel charges for beach chairs which I never encountered with other hotels. The staff is not so friendly, especially the concierge named "Sharp" (?) that she should not be in this business. The restaurants ...
Reviewed on Apr 10, 2026
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
$958 nightly
The price is $1,137 total per night from Apr 15 to Apr 16
$1,137 total
Apr 15 - Apr 16
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 ...
9.2/10 Wonderful! (1,000 reviews)
The rooms were amazing and view was great. Beach was quite dirty and lots of debris. The pools had a broken heater and were not swimable due to how cold they were
Reviewed on Apr 7, 2026
Four Seasons Resort Lanai
1 Manele Bay Road Lanai City HI
$1,005 nightly
The price is $1,193 total per night from Apr 12 to Apr 13
$1,193 total
Apr 12 - Apr 13
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. ...
9.8/10 Exceptional! (225 reviews)
We are "stuck" here for an extra 2 days due to the Kona stirm. Staff have been exceedingy patient and friendly and accommodating during this challenging peroid. They even got me to the local emergency room for treatment of an acute injury. Our room was gorgeous!
Reviewed on Mar 14, 2026
Sensei Lanai, A Four Seasons Resort
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, ...
9.8/10 Exceptional! (139 reviews)
Great experience. Very friendly staff. They have plenty of completely activities that you can partake aside from those that are listed on their website.
Reviewed on Jan 30, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
$887 nightly
The price is $1,054 total per night from Apr 25 to Apr 26
$1,054 total
Apr 25 - Apr 26
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 ...
9.4/10 Exceptional! (1,002 reviews)
Beautiful hotel, very unique experience. Everyone was very nice and helpful. We enjoyed our stay
Reviewed on Apr 8, 2026
The Resort at Kapalua Bay, Maui
One Bay Drive Lahaina HI
$1,784 nightly
The price is $2,118 total per night from Apr 16 to Apr 17
$2,118 total
Apr 16 - Apr 17
Total with taxes and fees
A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a children's ...
9.6/10 Exceptional! (211 reviews)
Even though we booked under the montage name, the hotel met all standards even with new ownership. The property itself is one of the most magical places we have been. We are very excited to come back in the future with our family.
Reviewed on Apr 3, 2026
Ho‘olei Villas at Grand Wailea
146 Ho'olei Circle Kihei HI
$2,036 nightly
The price is $2,417 total per night from Apr 16 to Apr 17
$2,417 total
Apr 16 - Apr 17
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! (45 reviews)
Womderful home, terrific service, access to hotel amenities was key.
Reviewed on Feb 28, 2026
Royal Lahaina Bungalows & Spa
2780 Kekaa Drive Lahaina HI
Fully refundableReserve now, pay when you stay
$388 nightly
The price is $460 total per night from Apr 28 to Apr 29
$460 total
Apr 28 - Apr 29
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! (9 reviews)
Our room was perfect with the kitchen our view was amazing we watched the whales from our room each morning.
Reviewed on Apr 4, 2026
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.
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
Maui Seaside Hotel
3 out of 5
Posted 8 hours ago
Travelocity Verified Review
"No coffee available in the front lobby; the one in the room was pretty bad.
Rooms are getting old and grungy. Difficult for people with walking challenges to get to the room. Elevator is too far away, and have to go down 4 steps in order to access it. Makes the place almost inaccessible, which is against the law, isn't it?"
A verified traveler stayed at Maui Seaside Hotel
