Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Aston Maui Hill
Save 100% on your flight
per person
May 16 - May 20
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to Kahului (OGG)
Stay at this 3-star aparthotel in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Maui Kaanapali Villas
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Hono Koa Vacation Club
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Black Rock are located nearby.
Royal Lahaina Resort & Bungalows
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Kahului (OGG)
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff 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
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 Black Rock are located nearby.
Fairmont Kea Lani Maui
Wailea
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Kahului (OGG)
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 condition in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby.
Aston at The Whaler on Kaanapali Beach
Save 100% on your flight
per person
May 10 - May 17
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Kahului (OGG)
Book a stay at this beach condo in Kaanapali. Enjoy free parking, a beach locale, and a 24-hour health club. 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
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 ...
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street, Kihei, HI
Stay at this 5-star luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...
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 Kamaole Beach Park 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.
Tue, May 6 - Fri, May 9
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Thu, Jul 24 - Wed, Jul 30
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Mon, Sep 22 - Mon, Sep 22
LAX
Los Angeles Intl.
OGG
Kahului
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Tue, Apr 22 - Wed, Apr 23
PDX
Portland Intl.
OGG
Kahului
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
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