Cheap Vacations in Wailea

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Wailea vacations

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

Maui Coast Hotel

3.5 out of 5
South Kihei
Price was $1,311, price is now $1,027 per person
$1,027
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was $2,182, price is now $1,541 per person
$1,541
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,890, price is now $1,342 per person
$1,342
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
Price was $1,884, price is now $1,340 per person
$1,340
per person
Apr 16 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Price was $2,122, price is now $1,570 per person
$1,570
per person
Apr 13 - Apr 19
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was $3,573, price is now $2,677 per person
$2,677
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Price was $1,787, price is now $1,387 per person
$1,387
per person
Apr 7 - Apr 13
found 15 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Kihei Kai Nani

Kihei Kai Nani

2.5 out of 5
South Kihei
Price was $1,384, price is now $1,081 per person
$1,081
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $3,776, price is now $2,989 per person
$2,989
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was $3,641, price is now $2,935 per person
$2,935
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kahului (OGG)

3-night Wailea vacations

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

Maui Banyan Vacation Club

3 out of 5
Price was $1,068, price is now $838 per person
$838
per person
Apr 28 - May 1
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
Price was $1,893, price is now $1,007 per person
$1,007
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was $1,435, price is now $974 per person
$974
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $1,382, price is now $974 per person
$974
per person
Apr 27 - Apr 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
Price was $1,383, price is now $1,008 per person
$1,008
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Price was $1,743, price is now $1,343 per person
$1,343
per person
Apr 28 - May 1
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $1,175, price is now $929 per person
$929
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Save 100% on your flight
Price was $3,387, price is now $2,693 per person
$2,693
per person
Apr 10 - Apr 13
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
Price was $2,144, price is now $1,705 per person
$1,705
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Price was $1,226, price is now $976 per person
$976
per person
Apr 28 - May 1
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3.5 out of 5
Price was $1,283, price is now $1,036 per person
$1,036
per person
Apr 28 - May 1
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Price was $1,092, price is now $883 per person
$883
per person
Apr 28 - May 1
found 13 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Kahului (OGG)

4-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Price was $1,126, price is now $766 per person
$766
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $1,884, price is now $1,340 per person
$1,340
per person
Apr 16 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Price was $1,710, price is now $1,247 per person
$1,247
per person
Apr 16 - Apr 20
found 13 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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 $4,391, price is now $3,229 per person
$3,229
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,632, price is now $1,211 per person
$1,211
per person
Apr 16 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Save 100% on your flight
Price was $3,776, price is now $2,989 per person
$2,989
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $1,959, price is now $1,566 per person
$1,566
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Price was $1,082, price is now $871 per person
$871
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,724, price is now $1,390 per person
$1,390
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Save 100% on your flight
Price was $2,549, price is now $2,097 per person
$2,097
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

4.5 out of 5
Price was $1,574, price is now $1,316 per person
$1,316
per person
Apr 16 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Price was $1,917, price is now $1,604 per person
$1,604
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

5-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was $1,509, price is now $1,076 per person
$1,076
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Price was $1,867, price is now $1,266 per person
$1,266
per person
Apr 29 - May 4
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 $2,182, price is now $1,541 per person
$1,541
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,890, price is now $1,342 per person
$1,342
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was $3,573, price is now $2,677 per person
$2,677
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kahului (OGG)
Kapalua Villas Maui

Kapalua Villas Maui

4 out of 5
Price was $2,052, price is now $1,589 per person
$1,589
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kihei Kai Nani

Kihei Kai Nani

2.5 out of 5
Price was $1,384, price is now $1,081 per person
$1,081
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Save 100% on your flight
Price was $6,368, price is now $5,024 per person
$5,024
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Save 100% on your flight
Price was $1,879, price is now $1,492 per person
$1,492
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was $3,641, price is now $2,935 per person
$2,935
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Price was $4,729, price is now $3,858 per person
$3,858
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Save 100% on your flight
Price was $2,623, price is now $2,158 per person
$2,158
per person
Apr 23 - Apr 28
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

6-7 night Wailea vacations

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

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,899, price is now $1,034 per person
$1,034
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
Price was $1,821, price is now $1,069 per person
$1,069
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,697, price is now $1,605 per person
$1,605
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $4,158, price is now $2,714 per person
$2,714
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $2,957, price is now $1,935 per person
$1,935
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Price was $2,907, price is now $1,908 per person
$1,908
per person
Apr 13 - Apr 19
found 10 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
Price was $2,051, price is now $1,371 per person
$1,371
per person
Apr 9 - Apr 16
found 8 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,859, price is now $1,992 per person
$1,992
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,153, price is now $1,503 per person
$1,503
per person
Apr 9 - Apr 16
found 8 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3.5 out of 5
Save 100% on your flight
Price was $1,953, price is now $1,381 per person
$1,381
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

3.5 out of 5
Save 100% on your flight
Price was $2,392, price is now $1,720 per person
$1,720
per person
Apr 20 - Apr 27
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Kahului (OGG)
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was $1,443, price is now $1,060 per person
$1,060
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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
$128 Roundtrip, found 8 hours ago
$128
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Oahu to Maui, returning Wed, Apr 29, priced at $128 found 8 hours ago
Tue, Sep 29 - Wed, Sep 30
HNL
Oahu
JHM
Kapalua
$151 Roundtrip, found 17 hours ago
$151
Roundtrip
found 17 hours ago
Select Southern Airways Express flight, departing Tue, Sep 29 from Oahu to Kapalua, returning Wed, Sep 30, priced at $151 found 17 hours ago
Sun, May 10 - Wed, May 13
OAK
Oakland
OGG
Maui
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sun, May 10 from Oakland to Maui, returning Wed, May 13, priced at $197 found 5 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
$1,026 nightly
The price is $1,218 total per night
$1,218 total
Apr 5 - Apr 6
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
$1,320 nightly
The price is $1,567 total per night
$1,567 total
Mar 9 - Mar 10
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
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
0.99 mi from Wailea
$1,035 nightly
The price is $1,229 total per night
$1,229 total
Mar 9 - Mar 10
Total with taxes and fees
With a stay at Fairmont Kea Lani Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Wailea Blue Golf Course.
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.