Book Exclusive Wailea Vacation Packages

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Wailea flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Kahana Villa

Kahana Villa

3 out of 5
Price was CA $2,502, price is now CA $1,380 per person
CA $1,380
per person
Dec 17 - Dec 24
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
Stay at this 3-star condo in Kahana. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Sands of Kahana

Sands of Kahana

3 out of 5
Price was CA $2,663, price is now CA $1,451 per person
CA $1,451
per person
Dec 17 - Dec 24
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
Stay at this 3-star beach aparthotel in Kahana. Enjoy free parking, a beach locale, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Price was CA $2,635, price is now CA $1,457 per person
CA $1,457
per person
Dec 17 - Dec 24
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
Stay at this 3-star condo in Napili. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was CA $2,510, price is now CA $1,419 per person
CA $1,419
per person
Jan 14 - Jan 21
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Kahului (OGG)
Stay at this 3-star beach condo in Kahana. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Price was CA $7,927, price is now CA $4,566 per person
CA $4,566
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this 3.5-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Popular attractions Kaanapali Beach and Whalers Village are located nearby.

Top Wailea hotels deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
The price is CA $808 per night
CA $808
CA $1,043 total
Nov 12 - Nov 13
includes taxes & fees
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 reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Hot tub
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is CA $772 per night
CA $772
CA $1,005 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this 4.5-star 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 our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Hot tub
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
The price is CA $1,068 per night
CA $1,068
CA $1,343 total
Nov 26 - Nov 27
includes taxes & fees
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 attractions Wailea Beach and Ulua Beach Park are located nearby.
Pool
Hot tub
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
The price is CA $1,057 per night
CA $1,057
CA $1,247 total
Oct 30 - Oct 31
includes taxes & fees
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 in our reviews. Popular attractions Wailea Beach and Polo Beach are located nearby.
Pool
Hot tub
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is CA $1,105 per night
CA $1,105
CA $1,386 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this 5-star luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Pool
Hot tub
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

4 out of 5
88 WAILEA IKE PLACE, Kihei, HI
Free cancellation
Reserve now, pay when you stay
The price is CA $511 per night
CA $511
CA $638 total
Oct 30 - Oct 31
includes taxes & fees
Stay at this 4-star hotel in Kihei. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Free WiFi
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See all available properties in Wailea
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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.

Popular places to visit

Wailea Beach which includes swimming, tropical scenes and a beach

Wailea Beach

4.5/5(295 reviews)

Nothing says vacation like spending a lazy day at Wailea Beach, a popular beach in Kihei. Wander the seaside or discover the beautiful sunsets in this romantic area.

Wailea Beach
Maluaka Beach featuring mountains, landscape views and rugged coastline

Maluaka Beach

4/5(25 reviews)

If a restful vacation is part of your travel plans, Maluaka Beach might be the perfect place to seek out during your trip to Kihei. Discover the beautiful sunsets in this romantic area, or enjoy its snorkeling spots.

Maluaka Beach
Makena Beach State Park showing a sandy beach

Makena State Park Beach

4.5/5(105 reviews)

If a restful vacation is part of your travel plans, Makena State Park Beach might be the perfect place to seek out during your trip to Kihei. Stroll along the seaside in this relaxing area, or seek out the snorkeling spots.

Makena State Park Beach

Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just CA $1,380. Make your travel fantasies come to life and secure your vacation with Travelocity today.
How long should my Wailea vacation be?
If you're looking for some guidance, most visitors spend roughly 6 nights vacationing in Wailea. But to discover the true essence of this place, stay a few extra days. You'll be able to tick off more attractions and really soak up the local vibe.
Where can I get the best vacation package deals for Wailea?
No matter your style, Travelocity can help you score an unbeatable Wailea package deal. The only thing you have to do is select a combination from our 400 air carriers and 1,000,000 worldwide properties.
Why should I book my Wailea vacation package via Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save on my Wailea car rental if I bundle it with hotels and flights?
With a Wailea vacation package, you can bundle your car, hotel and flight bookings and save loads. If you'd love to see the best of this impressive area, why not make a beeline for Diamond Head? This well-known sight is 153 kilometers from Wailea. With your own set of wheels, you'll be there in no time.
Which airport is best for Wailea?
Many people choose to fly into Kahului Airport (OGG), 23 kilometers north of downtown Wailea. Others prefer Molokai Airport (MKK) (88 kilometers away from central Wailea) or Lanai Airport (LNY) (56 kilometers away from central Wailea).
What is there to do in Wailea?
Wailea is brimming with things to see and do, like Wailea Beach and Makena State Park Beach. These two impressive attractions top most tourists' travel schedules.
Where should I stay when visiting Wailea?
The Palms At Wailea Maui is popular with many travelers. Book soon to avoid missing out.

Photos of local treasures

Browse Wailea vacation photos for more inspiration

Maluaka Beach showing landscape views, a beach and tropical scenes
Wailea
Wailea Beach featuring a park and tropical scenes as well as a couple
Wailea Beach which includes tropical scenes, a beach and swimming
Wailea