Cheap Vacations in Wailea

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Wailea vacations

Prices and availability subject to change. Additional terms may apply.
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wailea Grand Champions - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3 out of 5
Wailea
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
per person
Jun 3 - Jun 8
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
Wailea
Save 100% on your flight
per person
Jun 9 - Jun 16
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

3-night Wailea vacations

Prices and availability subject to change. Additional terms may apply.
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
per person
Jun 6 - Jun 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

4-night Wailea vacations

Prices and availability subject to change. Additional terms may apply.
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wailea Grand Champions - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3 out of 5
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
per person
Jun 7 - Jun 11
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)
Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
Save 100% on your flight
per person
May 29 - Jun 2
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
May 27 - May 31
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Polo Beach - CoralTree Residence Collection

Polo Beach - CoralTree Residence Collection

3.5 out of 5
Save 100% on your flight
per person
May 31 - Jun 4
Roundtrip flight included
San Francisco (SFO) to Kahului (OGG)

5-night Wailea vacations

Prices and availability subject to change. Additional terms may apply.
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Save 100% on your flight
per person
May 25 - May 30
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 12 - Jun 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

6-7 night Wailea vacations

Prices and availability subject to change. Additional terms may apply.
Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 21
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 16
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 11
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 16
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wailea Grand Champions - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 7
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
per person
May 31 - Jun 7
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 16
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

Flight deals to Wailea

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, May 6 - Wed, May 8
HNL
Honolulu
JHM
Kapalua
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Southern Airways Express flight, departing Mon, May 6 from Honolulu to Kapalua, returning Wed, May 8, priced at $118 found 4 days ago
Wed, May 1 - Thu, May 2
HNL
Honolulu
OGG
Kahului
$134 Roundtrip, found 10 hours ago
$134
Roundtrip
found 10 hours ago
Select Hawaiian Airlines flight, departing Wed, May 1 from Honolulu to Kahului, returning Thu, May 2, priced at $134 found 10 hours ago
Tue, May 7 - Thu, May 9
LAX
Los Angeles
OGG
Kahului
$218 Roundtrip, found 4 days ago
$218
Roundtrip
found 4 days ago
Select Hawaiian Airlines flight, departing Tue, May 7 from Los Angeles to Kahului, returning Thu, May 9, priced at $218 found 4 days ago

Top rated hotels for your Wailea vacation

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
0.45 mi from Wailea
The price is $781 per night
$781
per night
May 19 - May 20
With a stay at Grand Wailea Maui, A Waldorf Astoria Resort in Kihei (Wailea), you'll be a 1-minute drive from Wailea Beach and 7 minutes from Kamaole Beach Park.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
0.99 mi from Wailea
The price is $1,029 per night
$1,029
per night
May 6 - May 7
With a stay at Fairmont Kea Lani Maui in Kihei (Wailea), you'll be a 2-minute drive from Wailea Beach and 8 minutes from Kamaole Beach Park.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
0.09 mi from Wailea
The price is $699 per night
$699
per night
May 10 - May 11
With a stay at Wailea Beach Resort - Marriott, Maui in Kihei (Wailea), you'll be within a 10-minute drive of Wailea Beach and Kamaole Beach Park.
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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.

^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.