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Wailea Vacation Packages

Wailea Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club
Royal Lahaina Resort & Bungalows
Aston Mahana at Kaanapali
Aston Maui Kaanapali Villas
Aston Kaanapali Shores
Castle Kama'ole Sands
Aston at The Whaler on Kaanapali Beach
Aston at Papakea Resort

3-4 Night Vacations in Wailea

Price found within the past 48 hours. Click for updated prices.
Hono Koa Vacation Club
Hilton Vacation Club Ka'anapali Beach Maui
Grand Wailea Maui, A Waldorf Astoria Resort
Napili Shores Maui by OUTRIGGER

5-7 Night Vacations in Wailea

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Maui Oceanfront
Courtyard Maui Kahului Airport
Hilton Vacation Club Ka'anapali Beach Maui
Sugar Beach Resort

Cheap Hotel Deals in Wailea

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
Book a stay at this beach resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
Book a stay at this beach 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
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
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
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Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
Wailea Beach Resort - Marriott, Maui
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
Stay at this 4.5-star luxury resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Andaz Maui at Wailea Resort - a concept by Hyatt
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

3.5 out of 5
88 WAILEA IKE PLACE, Kihei, HI
Stay at this 3.5-star hotel in Kihei. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition ...
AC Hotel by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

3.5 out of 5
75 Wailea Ike, Kihei, HI
Stay at this 3.5-star business-friendly hotel in Kihei. Enjoy free breakfast, a free beach shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
Residence Inn by Marriott Maui Wailea
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
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
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Southern Airways Express
Hawaiian Airlines
Bargain Flight
United

Find cheap hotels in Wailea

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Wailea hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Wailea.

Choosing the right hotel in Hawaii has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Wailea’s 1,165 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $565. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Wailea hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Wailea. No matter your reason for visiting Wailea, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Wailea hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Wailea for as low as $565.

How many hotels are there in Wailea?

With over 1,165 hotels in Wailea, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $565.

How to find cheap car rentals in Wailea?

Finding a cheap car rental deal in Kihei is as easy as scoring cheap hotels in Wailea. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Wailea now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Wailea right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.