Book Exclusive Wailea Vacation Packages

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Wailea flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
Price was CA $2,510, price is now CA $1,993 per person
CA $1,993
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kahului (OGG)
Stay at this B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual Arts Center are located nearby.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was CA $2,912, price is now CA $2,070 per person
CA $2,070
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was CA $3,423, price is now CA $2,449 per person
CA $2,449
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Price was CA $4,862, price is now CA $3,666 per person
CA $3,666
per person
Aug 16 - Aug 21
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Kahului (OGG)
Book a stay at this 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 Grand Wailea are located nearby.
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
Price was CA $3,147, price is now CA $2,571 per person
CA $2,571
per person
Sep 14 - Sep 19
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Kahului (OGG)
Book a stay at this luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. 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 $1,150 per night
CA $1,150
CA $1,457 total
Jul 31 - Aug 1
includes taxes & fees
Book a stay at this 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 Grand Wailea are located nearby.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,546 per night
CA $1,546
CA $1,920 total
Jul 20 - Jul 21
includes taxes & fees
Book a stay at this 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
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 $1,342 per night
CA $1,342
CA $1,686 total
Jul 3 - Jul 4
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Polo Beach are located nearby.
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 $964 per night
CA $964
CA $1,244 total
Jul 20 - Jul 21
includes taxes & fees
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 our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
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 $1,084 per night
CA $1,084
CA $1,370 total
Jul 13 - Jul 14
includes taxes & fees
Book a stay at this 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.
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street Kihei HI
Free cancellation
Reserve now, pay when you stay
The price is CA $975 per night
CA $975
CA $1,242 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
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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.

Stay near popular Wailea attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

Wailea Beach

9.4/10 (4,138 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.
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Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just CA $1,993. 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

A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.
A vibrant coral reef with diverse marine life, including a yellow and black fish and a red sea anemone.
A pathway flanked by lush greenery and palm trees, leading to a building with a red roof.
A beach with rocky foreground, palm trees, and a golf course in the background.
A golf course with sand bunkers, green grass, two trees, a mountain, and a body of water.

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