Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Aston at Papakea Resort
Save 100% on your flight
per person
Mar 27 - Apr 2
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, 2 spa tubs, and breakfast (surcharge). Popular attractions Kaanapali Beach and Black Rock are located nearby.
Aston Maui Kaanapali Villas
Save 100% on your flight
per person
Mar 27 - Apr 2
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.
Kahana Beach Vacation Club
Save 100% on your flight
per person
Apr 13 - Apr 19
found 1 day ago
Roundtrip 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.
Maui Beach Vacation Club
Save 100% on your flight
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Maalaea Harbor are located nearby.
Aston Kaanapali Shores
Save 100% on your flight
per person
Mar 27 - Apr 2
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.
The Gardens at West Maui
Save 100% on your flight
per person
Mar 27 - Apr 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this 3-star condo in Kapalua. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
per person
Mar 27 - Apr 2
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.
Hono Koa Vacation Club
Save 100% on your flight
per person
Mar 29 - Apr 5
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 Black Rock 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 ...
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 ...
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 ...
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. ...
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.
Tue, Apr 15 - Wed, Apr 16
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Thu, Jun 19 - Thu, Jun 26
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Mon, Mar 17 - Tue, Mar 25
SFO
San Francisco Intl.
OGG
Kahului
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Tue, May 13 - Tue, May 20
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
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