Cheap Vacations in Wailea

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Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $1,192, price is now $853 per person
$853
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,313, price is now $1,323 per person
$1,323
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $2,145, price is now $1,335 per person
$1,335
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,154, price is now $1,384 per person
$1,384
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $2,467, price is now $1,633 per person
$1,633
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
Save 100% on your flight
Price was $1,582, price is now $1,111 per person
$1,111
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $1,001 per person
$1,001
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
Price was $1,247, price is now $904 per person
$904
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Kapalua Villas Maui

Kapalua Villas Maui

4 out of 5
Save 100% on your flight
Price was $1,845, price is now $1,347 per person
$1,347
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $2,275, price is now $1,661 per person
$1,661
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)

3-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
Price was $1,070, price is now $718 per person
$718
per person
Jan 22 - Jan 25
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,779, price is now $1,097 per person
$1,097
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,268, price is now $790 per person
$790
per person
Jan 20 - Jan 23
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $1,409, price is now $933 per person
$933
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,285, price is now $921 per person
$921
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $1,271, price is now $918 per person
$918
per person
Jan 26 - Jan 29
found 6 hours ago
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
Price was $1,908, price is now $1,414 per person
$1,414
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $1,854, price is now $1,383 per person
$1,383
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Kahului (OGG)
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
Price was $982, price is now $738 per person
$738
per person
Feb 10 - Feb 13
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,435, price is now $1,082 per person
$1,082
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,302, price is now $988 per person
$988
per person
Jan 22 - Jan 25
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,139, price is now $866 per person
$866
per person
Feb 10 - Feb 13
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

4-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $1,192, price is now $853 per person
$853
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,313, price is now $1,323 per person
$1,323
per person
Feb 8 - Feb 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $1,936, price is now $1,217 per person
$1,217
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,825, price is now $1,192 per person
$1,192
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,913, price is now $2,047 per person
$2,047
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was $1,350, price is now $955 per person
$955
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,414, price is now $1,030 per person
$1,030
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,476, price is now $1,095 per person
$1,095
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $1,841, price is now $1,376 per person
$1,376
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
Price was $1,335, price is now $1,011 per person
$1,011
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Save 100% on your flight
Price was $1,746, price is now $1,327 per person
$1,327
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,928, price is now $1,468 per person
$1,468
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)

5-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
Price was $1,247, price is now $904 per person
$904
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,895, price is now $1,098 per person
$1,098
per person
Jan 17 - Jan 22
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Save 100% on your flight
Price was $2,145, price is now $1,335 per person
$1,335
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,154, price is now $1,384 per person
$1,384
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $2,467, price is now $1,633 per person
$1,633
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $2,112, price is now $1,467 per person
$1,467
per person
Jan 17 - Jan 22
found 23 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $5,150, price is now $3,596 per person
$3,596
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,227 per person
$1,227
per person
Feb 11 - Feb 16
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
Save 100% on your flight
Price was $1,582, price is now $1,111 per person
$1,111
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $1,001 per person
$1,001
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
Kapalua Villas Maui

Kapalua Villas Maui

4 out of 5
Save 100% on your flight
Price was $1,845, price is now $1,347 per person
$1,347
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $2,275, price is now $1,661 per person
$1,661
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)

6-7 night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
AEI at Papakea Resort Maui

AEI at Papakea Resort Maui

3.5 out of 5
Price was $1,546, price is now $1,290 per person
$1,290
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,341, price is now $1,437 per person
$1,437
per person
Jan 17 - Jan 23
found 13 hours ago
Roundtrip flight included
Minneapolis (MSP) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,954, price is now $1,343 per person
$1,343
per person
Jan 26 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $2,247, price is now $1,548 per person
$1,548
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $2,189, price is now $1,564 per person
$1,564
per person
Jan 24 - Jan 30
found 1 day ago
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
Price was $4,889, price is now $3,796 per person
$3,796
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Save 100% on your flight
Price was $2,269, price is now $1,815 per person
$1,815
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Save 100% on your flight
Price was $2,130, price is now $1,721 per person
$1,721
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wonderful Honokowai Beach Condos

Wonderful Honokowai Beach Condos

4 out of 5
Save 100% on your flight
Price was $1,819, price is now $1,506 per person
$1,506
per person
Jan 26 - Feb 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Kalama Residence

The Kalama Residence

3 out of 5
Save 100% on your flight
Price was $4,362, price is now $3,616 per person
$3,616
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Kahului (OGG)
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
Save 100% on your flight
Price was $2,280, price is now $1,903 per person
$1,903
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
Save 100% on your flight
Price was $4,127, price is now $3,478 per person
$3,478
per person
Feb 9 - Feb 16
found 1 day ago
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.

Sat, Apr 25 - Wed, Apr 29
HNL
Oahu
OGG
Maui
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Sat, Apr 25 from Oahu to Maui, returning Wed, Apr 29, priced at $123 found 1 day ago
Sun, Mar 29 - Mon, Apr 20
YVR
Vancouver
OGG
Maui
$231 Roundtrip, found 13 hours ago
$231
Roundtrip
found 13 hours ago
Select WestJet flight, departing Sun, Mar 29 from Vancouver to Maui, returning Mon, Apr 20, priced at $231 found 13 hours ago
Thu, Feb 12 - Thu, Feb 19
LAX
Los Angeles
OGG
Maui
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Feb 12 from Los Angeles to Maui, returning Thu, Feb 19, priced at $238 found 1 day 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
$740 nightly
The price is $878 total per night
$878 total
Jan 6 - Jan 7, 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

Four Seasons Resort Maui at Wailea

5 out of 5
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

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
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
Don't see what you're looking for?
See all available properties in Wailea
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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.