Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Featured Wailea Boutique Hotels

See all 765 Hotels in Wailea
Wailea Beach Villas, A Destination Luxury Hotel

Wailea Beach Villas, A Destination Luxury Hotel

3800 Wailea Alanui Drive, Wailea
4.5 out of 5.0
5.0 out of 5 (50 reviews)
ParadiseThe location was fantastic. The hotel was superb.
  Aug 23, 2017
Hotel Wailea, Relais & Chateaux

Hotel Wailea, Relais & Chateaux

555 Kaukahi Street, Wailea
4.5 out of 5.0
4.6 out of 5 (329 reviews)
Best hotel in MauiAmazing start to finish. Highly recommend this hotel if you are looking for a quiet relaxing piece of paradise.
  Sep 11, 2017



Recently booked Boutique Hotels in Wailea

Wailea Beach Resort - Marriott, Maui
4.0 out of 5.0
Last booking: 6 hours ago
Residence Inn by Marriott Maui Wailea
3.0 out of 5.0
Last booking: 7 hours ago
Four Seasons Resort Maui at Wailea
5.0 out of 5.0
Last booking: 10 hours ago
Wailea Ekahi Village, A Destination Residence
3.0 out of 5.0
Last booking: 11 hours ago
Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 out of 5.0
Last booking: 13 hours ago
Fairmont Kea Lani Maui
4.5 out of 5.0
Last booking: 14 hours ago
Makena Surf, A Destination Residence
4.0 out of 5.0
Last booking: 18 hours ago
Grand Wailea - A Waldorf Astoria Resort
4.5 out of 5.0
Last booking: 41 hours ago
Wailea Beach Villas, A Destination Luxury Hotel
4.5 out of 5.0
Last booking: 43 hours ago

Book a Wailea Boutique Hotel that is Uniquely You

Wherever you might visit, you always bring your one-of-a-kind self on your trip, and Expedia provides great rates at the coolest and most designer properties in the area. Take a deep breath when you step out of the airport and inhale the unbelievable sense of just answering to yourself. When you land in Wailea you'll discover that all your worries are left behind and you can relax for the next several days.

Petite Lodging with Enormous Personality

These smaller hotels love boasting their offbeat charisma, unlike big chain hotels that aspire to satisfy everybody. And with your fashion-forward mind-set and a desire to step to your own beat, part of the ideal vacation is discovering a hotel in Wailea that embodies you. Many boutique hotels have characteristics like:

  • An idiosyncratic style you will not be able to find in bigger hotels, from individually decorated rooms to intimate bars, and conveniences that make them seem like home.
  • An exclusive stay, as boutique hotels generally have fewer than a hundred rooms.
  • A highly personalized type of service, where they add thoughtful touches like freshly baked cupcakes.
  • A premier address in the heart of the city. You'll be a short walk away from the city's hottest sites.

Immerse Yourself in Everything Wailea Offers!

Wailea has rooms to please most anyone that that will create a stay memorable.

Book a Room with Views Inside and Out in Wailea

Expedia makes it simple to select your perfect place to stay when you visit Wailea. Your Wailea boutique hotel is only a few taps away. From hotels that weave modern touches with classic styling to ones that deliver you to a completely new world, you are sure to find a hotel that is tailor-made for you.