Explore top 2026 5 Star Hotels in Wailea-Makena

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Top Wailea-Makena 5 Star hotels

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 Sep 18 to Sep 19
$1,375 total
Sep 18 - Sep 19
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
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 Sep 14 to Sep 15
$933 total
Sep 14 - Sep 15
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 Sep 2 to Sep 3
$1,045 total
Sep 2 - Sep 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)
"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"

Reviewed on Aug 25, 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
$738 nightly
The price is $876 total per night from Sep 2 to Sep 3
$876 total
Sep 2 - Sep 3
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, ...
9.2/10 Wonderful! (1,008 reviews)
"Lovely, partial ocean view room in a quiet location. Housekeeper was excellent, keeping our room in pristine condition. However the room decor was dark and dated for such a quality resort. A stunning location."

Reviewed on Sep 1, 2026

Opens in a new windowWailea Beach Resort - Marriott, 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
$806 nightly
The price is $956 total per night from Sep 16 to Sep 17
$956 total
Sep 16 - Sep 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 laundry service, conference center, and valet ...
9.4/10 Exceptional! (1,000 reviews)
"Everything was excellent! The room, the amenities and staff! I had one meal—breakfast, and that too was perfection!"

Reviewed on Sep 1, 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
$1,776 nightly
The price is $2,108 total per night from Sep 15 to Sep 16
$2,108 total
Sep 15 - Sep 16
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
Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom

5 out of 5
3200 Wailea Alanui Dr Kihei HI
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, ...
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Opens in a new windowVilla, Garden View, 2-bedroom
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A Kihei HI
$3,168 nightly
The price is $3,761 total per night from Sep 27 to Sep 28
$3,761 total
Sep 27 - Sep 28
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
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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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.

Recent Wailea-Makena hotel reviews by fellow wanderers

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
Posted 10 hours ago
Travelocity Verified Review
"Lovely, partial ocean view room in a quiet location. Housekeeper was excellent, keeping our room in pristine condition. However the room decor was dark and dated for such a quality resort. A stunning location."
A verified traveler stayed at Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui

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