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5 Star Hotels in Olowalu

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Featured 5 Star Olowalu Hotels

Grand Wailea Maui, A Waldorf Astoria Resort
5 out of 5
  • 42 min drive from Kaanapali Beach
The price is $1,139 per night from Jan 26 to Jan 27
$1,139
includes taxes & fees
Jan 26 - Jan 27
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea
5 out of 5
  • 43 min drive from Kaanapali Beach
The price is $849 per night from Feb 3 to Feb 4
$849
includes taxes & fees
Feb 3 - Feb 4
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Four Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua
5 out of 5
  • 15 min drive from Kaanapali Beach
The price is $1,104 per night from Jan 24 to Jan 25
$1,104
includes taxes & fees
Jan 24 - Jan 25
Stay at this 5-star luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
The Ritz-Carlton Maui, Kapalua
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Sensei Lanai, A Four Seasons Resort
5 out of 5
  • 21 min drive from Kaanapali Beach
Stay at this 5-star luxury hotel in Lanai City. Enjoy free WiFi, free parking, and a golf course. Popular attractions Lanai Pine Sporting Clays and Cavendish ...
Sensei Lanai, A Four Seasons Resort
Four Seasons Resort Lanai
5 out of 5
  • 32 min drive from Kaanapali Beach
The price is $1,551 per night from Feb 4 to Feb 5
$1,551
includes taxes & fees
Feb 4 - Feb 5
Stay at this 5-star luxury resort in Lanai City. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the property condition in our ...
Four Seasons Resort Lanai
Hotel Wailea, Relais & Chateaux - Adults Only
5 out of 5
Fully refundableReserve now, pay when you stay
  • 43 min drive from Kaanapali Beach
The price is $1,296 per night from Feb 1 to Feb 2
$1,296
includes taxes & fees
Feb 1 - Feb 2
Stay at this 5-star luxury resort in Kihei. Enjoy a full-service spa, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
5 out of 5
  • 14 min drive from Kaanapali Beach
The price is $1,616 per night from Jan 29 to Jan 30
$1,616
includes taxes & fees
Jan 29 - Jan 30
Stay at this 5-star luxury hotel in Kapalua. Enjoy free WiFi, a full-service spa, and a beach locale. Popular attractions Kaanapali Beach and Napili Bay are ...
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
5 out of 5
  • 42 min drive from Kaanapali Beach
The price is $2,352 per night from Jan 27 to Jan 28
$2,352
includes taxes & fees
Jan 27 - Jan 28
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Wailea Beach and Shops at Wailea ...
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
5 out of 5
  • 43 min drive from Kaanapali Beach
The price is $2,675 per night from Jan 26 to Jan 27
$2,675
includes taxes & fees
Jan 26 - Jan 27
Stay at this 5-star luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Popular attractions Wailea Beach and Polo Beach are ...
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
5 out of 5
  • 42 min drive from Kaanapali Beach
Stay at this 5-star luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...
Wailea Luxury Hilltop Resort Vistas
Oceanfront Kihei Paradise Vistas
5 out of 5
  • 31 min drive from Kaanapali Beach
Stay at this 5-star luxury apartment in Kihei. Enjoy free WiFi, free parking, and a garden. Popular attractions Wailea Beach and Waipuilani Park are located ...
Oceanfront Kihei Paradise Vistas
Upscale Luxurious Ocean Resort Vistas
5 out of 5
  • 38 min drive from Kaanapali Beach
Stay at this 5-star luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Kihei Boat Ramp are located ...
Upscale Luxurious Ocean Resort Vistas
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5-Star Hotel in Olowalu

It’s time. No more meh motels and so-so stays. This vacation it’s all about living it up, and that starts with a great hotel. You want first-class service and award-winning restaurants. Well, let us introduce you to a 5-star hotel in Olowalu.

So nice you’ll blink twice

What makes a hotel worthy of supreme star-age? For starters, the service has to be top-notch and personalized. These hotels often have 24-hour room service, a welcome gift upon your arrival, and help you with your bags—even if you travel light.

Are they nicer? Heck yeah, they are! Most 5-star hotels have jaw-dropping aesthetics that give an authentic feel of class. And we’re not talking about that faux-gold soap dish your Aunt Tilda puts out for the guests—it’s the real deal.

Stars in your eyes

Are 5-stars hotels worth it? If you like the finer things in life, then yes, they sure are. But we also know you’re the type that likes to get your caviar on a fish stick budget. We’re right there with you, and that is why we make it easy to find the best 5-star hotel in Olowalu for you. Sort by:

  • Price: Want to live large, but keep that budget balanced? We got you. We have 5-star hotels starting at $849.

  • Amenities: Olowalu skyline view? Maybe a heated indoor pool? Looking for a Michelin-star restaurant? Search for the hotels that have the amenities you desire.

  • Hotwire Hot Rate: We’ll tell you the name of the hotel after you book, and you might just save a ton.

When you’re looking for the top 5-star hotels in Olowalu—but don’t want to pay top dollar—let us help you out. You can get that posh palace of your dreams, and have money left to take on Olowalu your way.