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
$813 nightly
The price is $965 total per night from Oct 29 to Oct 30
$965 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
$1,080 nightly
The price is $1,282 total per night from Nov 15 to Nov 16
$1,282 total
Nov 15 - Nov 16
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! (1,001 reviews)
"The Four Seasons Wailea is a truly exceptional property. The Amenities were all first class and service was in a class of its own. Our experience met and exceeded all expectations on all measures."

Reviewed on Oct 16, 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
$629 nightly
The price is $747 total per night from Nov 15 to Nov 16
$747 total
Nov 15 - Nov 16
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! (1,001 reviews)
"Loved the check in process with Judy, she’s fantastic!! Ate at one of the on site restaurants food and service was amazing. Did not like the $61 a night valet parking fee"

Reviewed on Oct 13, 2026

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
$1,118 nightly
The price is $1,327 total per night from Oct 24 to Oct 25
$1,327 total
Oct 24 - Oct 25
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 Maui

Hotel Wailea Maui

5 out of 5
555 Kaukahi Street, Maui Wailea HI
Fully refundableReserve now, pay when you stay
$866 nightly
The price is $1,028 total per night from Nov 2 to Nov 3
$1,028 total
Nov 2 - Nov 3
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 free WiFi in public areas, laundry service, ...
9.4/10 Exceptional! (1,000 reviews)
"Spacious and updates rooms with everything you need. The service is simply outstanding. The pool was never crowded. The food at the restaurants was so good!"

Reviewed on Oct 15, 2026

Opens in a new windowHotel Wailea Maui
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 Nov 9 to Nov 10
$2,108 total
Nov 9 - Nov 10
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
$2,768 nightly
The price is $3,286 total per night from Nov 1 to Nov 2
$3,286 total
Nov 1 - Nov 2
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
$1,240 nightly
The price is $1,472 total per night from Oct 19 to Oct 20
$1,472 total
Oct 19 - Oct 20
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

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
Posted 17 hours ago
Travelocity Verified Review
"The Four Seasons Wailea is a truly exceptional property. The Amenities were all first class and service was in a class of its own. Our experience met and exceeded all expectations on all measures."
A verified traveler stayed at Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea

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