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 11 - Mar 19
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 11 - Mar 19
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 Napili Bay are located nearby.
Aston Kaanapali Shores
Save 100% on your flight
per person
Mar 11 - Mar 19
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 Napili Bay are located nearby.
Maui Coast Hotel
per person
Mar 11 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 3.5-star hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby.
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
per person
Mar 6 - Mar 13
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.
AEI at The Whaler Kaanapali Beach Resort
Save 100% on your flight
per person
Mar 12 - Mar 17
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 4-star beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Aston Mahana at Kaanapali
Save 100% on your flight
per person
Mar 6 - Mar 13
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 Napili Bay 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 ...
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 ...
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 ...
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.
Thu, Feb 13 - Wed, Feb 19
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Mon, Feb 10 - Wed, Feb 12
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$174 Roundtrip, found 4 days ago
$174
Roundtrip
found 4 days ago
Tue, Feb 18 - Tue, Feb 25
LAX
Los Angeles Intl.
OGG
Kahului
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Tue, Feb 11 - Tue, Feb 11
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$242 Roundtrip, found 4 days ago
$242
Roundtrip
found 4 days ago
Discover Other Travel Deals
- Wailea Beach Vacations
- Makena State Park Beach Vacations
- Maluaka Beach Vacations
- Polo Beach Vacations
- Shops at Wailea Vacations
- Little Beach Vacations
- Ulua Beach Vacations
- Wailea Emerald Golf Course Vacations
- Wailea Shopping Village Shopping Center Vacations
- Wailea Gold Golf Course Vacations
- Ulua Beach Park Vacations
- Wailea Blue Golf Course Vacations