Explore top 2026 5 Star Hotels in Wailea-Makena

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Top Wailea-Makena 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$786 nightly
The price is $933 total per night from Oct 29 to Oct 30
$933 total
Oct 29 - Oct 30
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, ...
Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$880 nightly
The price is $1,045 total per night from Oct 2 to Oct 3
$1,045 total
Oct 2 - Oct 3
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. There's fun for all ages with a free kid's club and a children's ...
9.6/10 Exceptional! (1,000 reviews)
"Incredible service and high end property. The rooms are updated with a nice balcony. 3 pools and direct beach access makes it easy."

Reviewed on Sep 24, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
3700 Wailea Alanui Dr Kihei HI
$662 nightly
The price is $786 total per night from Oct 30 to Oct 31
$786 total
Oct 30 - Oct 31
Total with taxes and fees
A full-service spa, 4 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a waterslide, ...
Opens in a new windowWailea Beach Resort - Marriott, Maui
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,158 nightly
The price is $1,375 total per night from Oct 23 to Oct 24
$1,375 total
Oct 23 - Oct 24
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 ...
Opens in a new windowFairmont Kea Lani Maui
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
$899 nightly
The price is $1,067 total per night from Oct 31 to Nov 1
$1,067 total
Oct 31 - Nov 1
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the laundry service, conference center, and ...
9.4/10 Exceptional! (1,002 reviews)
"Everything was excellent, form the location to the incredible food!"

Reviewed on Sep 22, 2026

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
$1,809 nightly
The price is $2,148 total per night from Oct 17 to Oct 18
$2,148 total
Oct 17 - Oct 18
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! (54 reviews)
"Amazing property with an incredible staff. A+++ all the way around!"

Reviewed on Aug 25, 2026

Opens in a new windowHo‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A Kihei HI
$2,668 nightly
The price is $3,167 total per night from Oct 12 to Oct 13
$3,167 total
Oct 12 - Oct 13
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 ...
Opens in a new windowFairmont Kea Lani Maui Villa Experience
Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom

5 out of 5
3200 Wailea Alanui Dr Kihei HI
$1,084 nightly
The price is $1,287 total per night from Oct 1 to Oct 2
$1,287 total
Oct 1 - Oct 2
Total with taxes and fees
This condo features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a terrace, ...
Opens in a new windowVilla, Garden View, 2-bedroom
Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas

5 out of 5
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! (3 reviews)
"The best place while we in Hawaii. The first time we had a place with cool Ac . Nice view . Gotta to stay here guys. Big kitchen and clean everywhere. Awesome bathroom, the mirror with light and the view from kitchen.. Amazing❤️"

Reviewed on Aug 11, 2026

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Opens in a new windowWailea Luxury Hilltop Resort Vistas
Upscale Luxurious Ocean Resort Vistas

Upscale Luxurious Ocean Resort Vistas

5 out of 5
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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Opens in a new windowUpscale Luxurious Ocean Resort Vistas
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Five Star Hotels in Wailea-Makena

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 five 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.

Recent Wailea-Makena hotel reviews by fellow wanderers

AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Lovely clean hotel with lovely staff and well located"
A verified traveler stayed at AC Hotel by Marriott Maui Wailea
AC Hotel by Marriott Maui Wailea

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