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Wailea Vacation Packages

Wailea Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Price was $1,600, price is now $1,236 per person
$1,236
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)
Book a stay at this golf condo in Kihei. Enjoy free WiFi, 5 outdoor tennis courts, and cable TV channels. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was $5,051, price is now $2,924 per person
$2,924
per person
Jul 28 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Kahului (OGG)
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 reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Price was $2,325, price is now $1,670 per person
$1,670
per person
Jul 21 - Jul 26
found 24 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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.
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
Save 100% on your flight
Price was $2,845, price is now $2,052 per person
$2,052
per person
Jul 27 - Aug 3
found 22 hours ago
Roundtrip flight included
San Francisco (SFO) 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.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $2,010, price is now $1,451 per person
$1,451
per person
Aug 2 - Aug 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. 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.
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Save 100% on your flight
Price was $4,349, price is now $3,222 per person
$3,222
per person
Aug 2 - Aug 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
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 reviews. Popular attractions Wailea Beach and Grand Wailea are located nearby.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $2,116, price is now $1,570 per person
$1,570
per person
Aug 2 - Aug 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Hip Hawaiian Seaside Vistas

Hip Hawaiian Seaside Vistas

3 out of 5
Central Kihei
Price was $2,029, price is now $1,572 per person
$1,572
per person
Aug 9 - Aug 15
found 1 day ago
Roundtrip flight included
San Francisco (SFO) 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.
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Price was $1,333, price is now $1,032 per person
$1,032
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
Price was $1,827, price is now $1,233 per person
$1,233
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $2,888, price is now $2,136 per person
$2,136
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Kahului (OGG)
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Price was $1,600, price is now $1,236 per person
$1,236
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)

5-7 Night Vacations in Wailea

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $2,010, price is now $1,451 per person
$1,451
per person
Aug 2 - Aug 8
found 10 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was $5,051, price is now $2,924 per person
$2,924
per person
Jul 28 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Price was $2,325, price is now $1,670 per person
$1,670
per person
Jul 21 - Jul 26
found 24 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Kahului (OGG)
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
Save 100% on your flight
Price was $2,845, price is now $2,052 per person
$2,052
per person
Jul 27 - Aug 3
found 22 hours ago
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)

Cheap Hotel Deals in Wailea

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
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 ...
Opens in a new windowFour Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
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 ...
Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
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 ...
Opens in a new windowWailea Beach Resort - Marriott, Maui
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Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
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 ...
Opens in a new windowAndaz Maui at Wailea Resort - a concept by Hyatt
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
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 ...
Opens in a new windowFairmont Kea Lani Maui
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

3.5 out of 5
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 ...
Opens in a new windowResidence Inn by Marriott Maui Wailea
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
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 ...
Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

4 out of 5
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 ...
Opens in a new windowAC Hotel by Marriott Maui Wailea
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.

Alaska Airlines
Wed, Aug 26 - Wed, Aug 26
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Wed, Aug 26 from Daniel K. Inouye Intl. to Kahului, returning Wed, Aug 26, priced at $133 found 1 hour ago
Southern Airways Express
Thu, Aug 27 - Fri, Sep 4
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Southern Airways Express flight, departing Thu, Aug 27 from Daniel K. Inouye Intl. to West Maui, returning Fri, Sep 4, priced at $198 found 1 day ago
Bargain Flight
Thu, Aug 27 - Thu, Aug 27
LAX
Los Angeles Intl.
OGG
Kahului
$291 Roundtrip, found 21 hours ago
$291
Roundtrip
found 21 hours ago
Select Bargain Flight flight, departing Thu, Aug 27 from Los Angeles Intl. to Kahului, returning Thu, Aug 27, priced at $291 found 21 hours ago
Bargain Flight
Mon, Aug 31 - Mon, Aug 31
OAK
Oakland Intl.
OGG
Kahului
$336 Roundtrip, found 1 day ago
$336
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Mon, Aug 31 from Oakland Intl. to Kahului, returning Mon, Aug 31, priced at $336 found 1 day ago