Explore top 2026 5 Star Hotels in Wailea-Makena

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

Tonight

Tomorrow

This weekend

Next weekend

Top Wailea-Makena 5 Star hotels

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$850 nightly

$1,009 total

Feb 21 - Feb 22

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! (1,002 reviews)

10/10 service, amazing room with gorgeous view!

Reviewed on Feb 19, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$716 nightly

$850 total

Mar 4 - Mar 5

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)

Beautiful room and view. Amazing pool area. So much fun for the entire family!

Reviewed on Feb 18, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$950 nightly

$1,128 total

Mar 7 - Mar 8

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 ...

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$1,075 nightly

$1,277 total

Mar 16 - Mar 17

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! (1,001 reviews)

Rooms are beautiful

Reviewed on Jan 13, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,153 nightly

$2,555 total

Mar 1 - Mar 2

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! (44 reviews)

We stayed in Villa 99-5. . To sum it up quickly, the price to experience was in our opinion way too high. Also as a member an elite member, I did not get the discounts on the Cabana rentals and beach chair. The restaurant staff and food was very good. For the price we believe that there should be ...

Reviewed on Oct 22, 2025

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

$3,448 nightly

$4,094 total

Mar 7 - Mar 8

Total with taxes and fees

A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with beach cabanas ...

Wailea Luxury Hilltop Resort Vistas

10 Wailea Ekolu Pl Kihei HI

This apartment features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.

10/10 Exceptional! (2 reviews)

We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back!

Reviewed on Nov 28, 2024

Get rates

Upscale Luxurious Ocean Resort Vistas

2777 S Kihei Rd Kihei HI

This apartment features 2 outdoor pools, a garden, and a picnic area. Enjoy the 2 hot tubs and get free self parking. Laundry facilities and a virtual front ...

Get rates

Don't see what you're looking for?

See all available properties in Wailea-Makena

View all properties

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.

Wailea-Makena 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 Wailea-Makena 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. Wailea-Makena 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 Wailea-Makena 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.