Explore top 2025 5 Star Hotels in Wailea-Makena

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Top Wailea-Makena 5 Star hotels

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI

$1,099 nightly

$1,296 total

Oct 26 - Oct 27

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! (1,013 reviews)

"Gorgeous place"

Reviewed on Sep 23, 2025

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

$702 nightly

$828 total

Oct 21 - Oct 22

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! (1,015 reviews)

"Stunning resort!"

Reviewed on Sep 15, 2025

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI

$755 nightly

$891 total

Oct 26 - Oct 27

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)

"Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again."

Reviewed on Sep 24, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street, Kihei, HI

Fully refundableReserve now, pay when you stay

$999 nightly

$1,178 total

Oct 19 - Oct 20

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)

"This place. So special. The crème de la creme. 5+stars. Cannot WAIT to go back!"

Reviewed on Sep 23, 2025

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle, Kihei, HI

$2,108 nightly

$2,487 total

Oct 3 - Oct 4

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! (42 reviews)

"Perfect for Families. Quite spacious and great for a relaxing Family vacation."

Reviewed on Jun 15, 2025

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A, Kihei, HI

$2,859 nightly

$3,372 total

Oct 3 - Oct 4

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 ...

9.6/10 Exceptional! (6 reviews)

"It’s a decent hotel to stay for the family."

Reviewed on Aug 22, 2024

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.

"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

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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 ...

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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.