Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Kihei Kai Nani
South Kihei
Price was $1,310, price is now $1,042 per person
$1,042
per person
May 15 - May 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach condo in Kihei. Enjoy free parking, a garden, and concierge services. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Hyatt Vacation Club at Ka'anapali Beach, Maui
Price was $3,769, price is now $3,030 per person
$3,030
per person
May 21 - May 25
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
Price was $2,911, price is now $1,957 per person
$1,957
per person
May 18 - May 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.
Palms at Wailea Maui
Wailea
Save 100% on your flight
Price was $3,571, price is now $2,417 per person
$2,417
per person
May 7 - May 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this golf aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach South are located nearby.
Royal Kahana Maui by OUTRIGGER
Price was $2,391, price is now $1,680 per person
$1,680
per person
May 17 - May 25
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this aparthotel in Kahana. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
Price was $3,604, price is now $2,572 per person
$2,572
per person
May 18 - May 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this luxury condo in Kaanapali. Enjoy free valet parking, 4 outdoor pools, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.
Sands of Kahana
Price was $3,583, price is now $2,589 per person
$2,589
per person
May 22 - May 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this 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.
Wailea Grand Champions - Maui Condo & Home
Wailea
Save 100% on your flight
Price was $1,811, price is now $1,332 per person
$1,332
per person
May 18 - May 23
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this golf condo in Kihei. Enjoy free WiFi, 5 outdoor tennis courts, and cable TV channels. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
3-4 Night Vacations in Wailea
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Wailea
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
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 ...
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
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 ...
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Wailea Beach Resort - Marriott, Maui
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 ...
Andaz Maui at Wailea Resort - a concept by Hyatt
3550 Wailea Alanui Dr Kihei HI
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 ...
AC Hotel by Marriott Maui Wailea
88 WAILEA IKE PLACE Kihei HI
Stay at this hotel in Kihei. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our ...
Residence Inn by Marriott Maui Wailea
75 Wailea Ike Kihei HI
Book a stay at this business-friendly hotel in Kihei. Enjoy free breakfast, a free beach shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street Kihei HI
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 ...
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.
Tue, Apr 28 - Tue, Apr 28
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$121 Roundtrip, found 7 hours ago
$121
Roundtrip
found 7 hours ago
Sun, May 31 - Sat, Jun 13
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$149 Roundtrip, found 5 days ago
$149
Roundtrip
found 5 days ago
Tue, Apr 28 - Wed, May 13
SFO
San Francisco Intl.
OGG
Kahului
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Mon, Apr 27 - Wed, Apr 29
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Discover Other Travel Deals
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- Shops at Wailea Vacations
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- Little Beach Vacations
- Ulua Beach Vacations
- Wailea Emerald Golf Course Vacations
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- Makena Golf Course Vacations
- Keawakapu Beach South Vacations