Search Deals onWailea Vacation Packages
Wailea Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Kahana Villa
Save 100% on your flight
Price was $2,032, price is now $1,475 per person
$1,475
per person
Feb 21 - Feb 26
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Stay at this condo in Kahana. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Kahana Beach Vacation Club
Save 100% on your flight
Price was $2,609, price is now $1,606 per person
$1,606
per person
Feb 20 - Feb 27
found 1 day ago
Roundtrip non-stop 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.
Palms at Wailea Maui
Wailea
Save 100% on your flight
Price was $3,487, price is now $2,367 per person
$2,367
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this golf aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach South are located nearby.
Hono Koa Vacation Club
Save 100% on your flight
Price was $2,982, price is now $2,071 per person
$2,071
per person
Feb 13 - Feb 18
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this 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.
Maui Banyan Vacation Club
South Kihei
Save 100% on your flight
Price was $3,109, price is now $2,167 per person
$2,167
per person
Feb 12 - Feb 19
found 9 hours ago
Roundtrip non-stop flight included
Anchorage (ANC) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a garden. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was $4,133, price is now $2,972 per person
$2,972
per person
Feb 12 - Feb 19
found 9 hours ago
Roundtrip non-stop flight included
Anchorage (ANC) 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.
Napili Kai Beach Resort
Save 100% on your flight
Price was $3,019, price is now $2,193 per person
$2,193
per person
Feb 20 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach hotel in Napili. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Kapalua Villas Maui
Save 100% on your flight
Price was $3,253, price is now $2,444 per person
$2,444
per person
Feb 12 - Feb 19
found 9 hours ago
Roundtrip non-stop flight included
Anchorage (ANC) to Kahului (OGG)
Book a stay at this golf aparthotel in Kapalua. Enjoy 3 outdoor pools, 8 restaurants, and 5 bars/lounges. Popular attractions Kaanapali Beach and Napili Bay 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 ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
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.
Tue, Jan 20 - Wed, Jan 21
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Mon, Mar 9 - Tue, Mar 17
SFO
San Francisco Intl.
OGG
Kahului
$236 Roundtrip, found 2 days ago
$236
Roundtrip
found 2 days ago
Mon, Jan 19 - Mon, Jan 26
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$247 Roundtrip, found 15 hours ago
$247
Roundtrip
found 15 hours ago
Wed, Mar 4 - Wed, Mar 4
LAX
Los Angeles Intl.
OGG
Kahului
$250 Roundtrip, found 16 hours ago
$250
Roundtrip
found 16 hours ago
Discover Other Travel Deals
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- Little Beach Vacations
- Wailea Gold Golf Course Vacations
- Mokapu Beach Vacations
- Wailea Blue Golf Course Vacations
- Ulua Beach Vacations
- Keawakapu Beach South Vacations
- Wailea Shopping Village Shopping Center Vacations