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
Price was $1,549, price is now $930 per person
$930
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
Napili Shores Maui by OUTRIGGER
Save 100% on your flight
Price was $2,372, price is now $1,422 per person
$1,422
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kahului (OGG)
Book a stay at this beach aparthotel in Napili. Enjoy free WiFi, free parking, and 2 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.
Royal Kahana Maui by OUTRIGGER
Save 100% on your flight
Price was $1,901, price is now $1,246 per person
$1,246
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kahului (OGG)
Stay at this aparthotel in Kahana. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Sands of Kahana
Save 100% on your flight
Price was $2,001, price is now $1,315 per person
$1,315
per person
Feb 23 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kahului (OGG)
Book a stay at this 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.
Royal Lahaina Resort & Bungalows
Price was $2,453, price is now $1,642 per person
$1,642
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Kahului (OGG)
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby.
The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was $3,533, price is now $2,392 per person
$2,392
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Kahului (OGG)
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
OUTRIGGER Kaanapali Beach Resort
Price was $2,679, price is now $1,818 per person
$1,818
per person
Mar 9 - Mar 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Kahului (OGG)
Book a stay at this 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.
OUTRIGGER Honua Kai Resort & Spa
Price was $3,430, price is now $2,361 per person
$2,361
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Kahului (OGG)
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, free valet 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.
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
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
Book a stay at this 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
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Andaz Maui at Wailea Resort - a concept by Hyatt
3550 Wailea Alanui Dr Kihei HI
Book a stay at this 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 ...
Residence Inn by Marriott Maui Wailea
75 Wailea Ike Kihei HI
Book a stay at this business-friendly hotel in Kihei. Enjoy free breakfast, a free beach shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
AC Hotel by Marriott Maui Wailea
88 WAILEA IKE PLACE Kihei HI
Stay at this hotel in Kihei. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our ...
Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street Kihei HI
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...
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 25 - Wed, Feb 25
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$95 Roundtrip, found 2 hours ago
$95
Roundtrip
found 2 hours ago
Thu, Feb 5 - Thu, Feb 12
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Wed, Feb 25 - Wed, Feb 25
OAK
Oakland Intl.
OGG
Kahului
$231 Roundtrip, found 10 hours ago
$231
Roundtrip
found 10 hours ago
Wed, Mar 25 - Wed, Mar 25
LAX
Los Angeles Intl.
OGG
Kahului
$231 Roundtrip, found 2 hours ago
$231
Roundtrip
found 2 hours ago
Discover Other Travel Deals
- Wailea Beach Vacations
- Maluaka Beach Vacations
- Makena State Park Beach Vacations
- Shops at Wailea Vacations
- Polo Beach Vacations
- Little Beach Vacations
- Mokapu Beach Vacations
- Wailea Gold Golf Course Vacations
- Ulua Beach Vacations
- Ulua Beach Park Vacations
- Wailea Blue Golf Course Vacations
- Po'olenalena Beach Vacations