Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club
Save 100% on your flight
per person
Mar 10 - Mar 15
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.
Aston Maui Kaanapali Villas
Save 100% on your flight
per person
Mar 10 - Mar 15
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 Black Rock are located nearby.
Aston Kaanapali Shores
Save 100% on your flight
per person
Mar 10 - Mar 15
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 Black Rock are located nearby.
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
per person
Mar 10 - Mar 15
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 Napili Bay are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
per person
Mar 10 - Mar 15
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 Napili Bay are located nearby.
Bamboo Valley Inn
per person
Mar 21 - Mar 26
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Kahului (OGG)
Stay at this 3.5-star B&B in Haiku. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Haleakala Bike Company and Hui Noʻeau Visual Arts Center 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
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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
Wailea Ekahi - CoralTree Residence Collection
3300 Wailea Alanui, Kihei, HI
Stay at this 3-star beach condo in Kihei. Enjoy free WiFi, free parking, and 4 outdoor pools. Popular attractions Wailea Beach and Mokapu Beach are located ...
Wailea Grand Champions - CoralTree Residence Collection
155 Wailea Ike Place, Kihei, HI
Stay at this 3-star golf condo in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...
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 ...
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 15 - Wed, Apr 16
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$114 Roundtrip, found 4 hours ago
$114
Roundtrip
found 4 hours ago
Thu, Feb 6 - Wed, Feb 12
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
OGG
Kahului
$198 Roundtrip, found 18 hours ago
$198
Roundtrip
found 18 hours ago
Mon, Mar 10 - Tue, Mar 18
OAK
Oakland Intl.
OGG
Kahului
$238 Roundtrip, found 6 days ago
$238
Roundtrip
found 6 days ago
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