Cheap Vacations in Wailea
- Wailea vacations
- 3-night Wailea vacations
- 4-night Wailea vacations
- 5-night Wailea vacations
- 6-7 night Wailea vacations
Wailea vacations
Price found within the past 48 hours. Click for updated prices.
3-night Wailea vacations
Price found within the past 48 hours. Click for updated prices.
4-night Wailea vacations
Price found within the past 48 hours. Click for updated prices.
5-night Wailea vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night Wailea vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to Wailea
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
HNL
Oahu
OGG
Maui
$123 Roundtrip, found 8 hours ago
$123
Roundtrip
found 8 hours ago
YVR
Vancouver
OGG
Maui
$231 Roundtrip, found 12 hours ago
$231
Roundtrip
found 12 hours ago
LAX
Los Angeles
OGG
Maui
$238 Roundtrip, found 10 hours ago
$238
Roundtrip
found 10 hours ago
Top rated hotels for your Wailea vacation
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
0.45 mi from Wailea
$740 nightly
The price is $878 total per night
$878 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at Grand Wailea Maui, A Waldorf Astoria Resort in Kihei (Wailea), you'll be within a 10-minute walk of Wailea Beach and Shops at Wailea.
Pool
Hot Tub
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
0.77 mi from Wailea
$755 nightly
The price is $891 total per night
$891 total
Dec 19 - Dec 20
Total with taxes and fees
With a stay at Four Seasons Resort Maui at Wailea in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
Pool
Hot Tub
Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr Kihei HI
0.09 mi from Wailea
$694 nightly
The price is $823 total per night
$823 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
With a stay at Wailea Beach Resort - Marriott, Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Shops at Wailea.
Pool
Hot Tub
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.
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Flights
^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.