Explore top 2026 5 Star Hotels in Wailea-Makena

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Top Wailea-Makena 5 Star hotels

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$795 nightly

$944 total

Jan 13 - Jan 14, 2026

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! (999 reviews)

This property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on Dec 2, 2025

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$740 nightly

$878 total

Jan 13 - Jan 14, 2026

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)

Very nice resort for a family vacation!

Reviewed on Dec 23, 2025

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$993 nightly

$1,178 total

Jan 8 - Jan 9, 2026

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! (1,000 reviews)

Spotless room, turn down service at night. Fantastic stay

Reviewed on Dec 28, 2025

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$1,099 nightly

$1,305 total

Jan 4 - Jan 5, 2026

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! (1,001 reviews)

This resort with private villas is spectacular. The rooms are beautifully appointed and perfectly clean with every amenity you need. We stayed in #52 that overlooked a lagoon and it couldn't have been nicer or more peaceful. Even though there are also ocean views, this was my favorite. The staff ...

Reviewed on Dec 26, 2025

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,055 nightly

$2,440 total

Jan 22 - Jan 23, 2026

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! (43 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

$2,939 nightly

$3,467 total

Jan 8 - Jan 9, 2026

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.