Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club
North Kihei
Price was $2,482, price is now $1,341 per person
$1,341
per person
Dec 10 - Dec 16
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 Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.
Maui Banyan Vacation Club
South Kihei
Price was $4,163, price is now $2,768 per person
$2,768
per person
Dec 25 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Hotel Wailea Maui
Wailea
Price was $10,483, price is now $7,509 per person
$7,509
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Wailea Ike by Avantstay Walk to the Beach Balcony w/ Views
Wailea
Price was $1,843, price is now $1,435 per person
$1,435
per person
Dec 15 - Dec 20
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this cottage in Kihei. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Worldmark Kihei
South Kihei
Price was $4,584, price is now $3,604 per person
$3,604
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Stay at this hotel in Kihei. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby.
Royal Lahaina Bungalows & Spa
Price was $2,749, price is now $2,179 per person
$2,179
per person
Dec 30 - Jan 5
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Polo Beach - CoralTree Residence Collection
Wailea
Price was $2,986, price is now $2,382 per person
$2,382
per person
Dec 15 - Dec 20
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Wailea Beach and Polo Beach are located nearby.
Hip Hawaiian Seaside Vistas
Central Kihei
Price was $2,885, price is now $2,336 per person
$2,336
per person
Dec 30 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Wailea Beach and Waipuilani Park 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
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 ...
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 ...
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
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 ...
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 ...
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 ...
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 ...
Hotel Wailea Maui
555 Kaukahi Street, Maui Kihei HI
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
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, Jan 12 - Tue, Feb 2
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$138 Roundtrip, just found
$138
Roundtrip
just found
Thu, Nov 26 - Fri, Nov 27
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
Fri, Nov 27 - Thu, Dec 17
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$323 Roundtrip, found 1 hour ago
$323
Roundtrip
found 1 hour ago
Tue, Jan 5 - Fri, Jan 22
OAK
Oakland Intl.
OGG
Kahului
$329 Roundtrip, found 6 hours ago
$329
Roundtrip
found 6 hours ago
Discover Other Travel Deals
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- Makena State Park Beach Vacations
- Shops at Wailea Vacations
- Polo Beach Vacations
- Ulua Beach Vacations
- Little Beach Vacations
- Mokapu Beach Vacations
- Makena Landing Park Vacations
- Grand Wailea Vacations
- Wailea Blue Golf Course Vacations