Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sands of Kahana
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Kahana Beach Vacation Club
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Hono Koa Vacation Club
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 3-star condo in Honokowai. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Aston Kaanapali Shores
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 4-star beach condo in Kaanapali. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Aston Maui Kaanapali Villas
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a full-service spa, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 3.5-star 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 Kaanapali Beach and Whalers Village are located nearby.
Aston Mahana at Kaanapali
Save 100% on your flight
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 3.5-star beach aparthotel in Kaanapali. Enjoy free WiFi, a beach locale, and a 24-hour front desk. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Kaanapali Beach and Whalers Village 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
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive, Kihei, HI
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 ...
Grand Wailea Maui, A Waldorf Astoria Resort
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Andaz Maui at Wailea Resort - a concept by Hyatt
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 ...
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr, Kihei, HI
Stay at this 4.5-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 ...
AC Hotel by Marriott Maui Wailea
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 ...
Residence Inn by Marriott Maui Wailea
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 ...
Hotel Wailea, Relais & Chateaux - Adults Only
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. ...
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.
Wed, Feb 12 - Wed, Feb 12
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Mon, Mar 24 - Thu, Mar 27
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$158 Roundtrip, found 4 hours ago
$158
Roundtrip
found 4 hours ago
Tue, Feb 11 - Tue, Feb 11
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$230 Roundtrip, found 17 hours ago
$230
Roundtrip
found 17 hours ago
Wed, Feb 12 - Wed, Feb 12
LAX
Los Angeles Intl.
OGG
Kahului
$231 Roundtrip, found 1 day ago
$231
Roundtrip
found 1 day ago
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