Cheap Vacations in Wailea

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Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Kihei Kai Nani

Kihei Kai Nani

2.5 out of 5
South Kihei
Price was $1,643, price is now $1,340 per person
$1,340
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Save 100% on your flight
Price was $2,154, price is now $1,512 per person
$1,512
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $2,300, price is now $1,818 per person
$1,818
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $6,454, price is now $5,150 per person
$5,150
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $2,738, price is now $2,190 per person
$2,190
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Price was $1,665, price is now $1,347 per person
$1,347
per person
Apr 16 - Apr 20
found 17 hours ago
Roundtrip flight included
Seattle (SEA) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Price was $2,490, price is now $2,026 per person
$2,026
per person
Apr 25 - Apr 30
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

3-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $958, price is now $705 per person
$705
per person
Apr 20 - Apr 23
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

3.5 out of 5
Save 100% on your flight
Price was $1,009, price is now $756 per person
$756
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Price was $1,628, price is now $1,228 per person
$1,228
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Price was $993, price is now $766 per person
$766
per person
Apr 16 - Apr 19
found 16 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
Price was $1,194, price is now $991 per person
$991
per person
Apr 10 - Apr 13
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

3.5 out of 5
Price was $1,014, price is now $862 per person
$862
per person
Apr 18 - Apr 21
found 22 hours 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 $4,466, price is now $3,802 per person
$3,802
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

4.5 out of 5
Price was $939, price is now $812 per person
$812
per person
Apr 16 - Apr 19
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
The Kalama Residence

The Kalama Residence

3 out of 5
Price was $1,070, price is now $926 per person
$926
per person
Apr 16 - Apr 19
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Beach House

Maui Beach House

2 out of 5
Price was $1,117, price is now $1,009 per person
$1,009
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Whale Watching From Your Lanai - Tropical Oceanfront 2-2 in West Maui

Whale Watching From Your Lanai - Tropical Oceanfront 2-2 in West Maui

2 out of 5
Price was $1,155, price is now $1,053 per person
$1,053
per person
Apr 18 - Apr 21
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hololani

Hololani

3 out of 5
Price was $1,300, price is now $1,188 per person
$1,188
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Seattle (SEA) 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 $1,302, price is now $923 per person
$923
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,710, price is now $1,090 per person
$1,090
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,468, price is now $942 per person
$942
per person
Apr 30 - May 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $4,275, price is now $2,970 per person
$2,970
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,801, price is now $1,296 per person
$1,296
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Kahana Villa

Kahana Villa

3 out of 5
Price was $1,496, price is now $1,090 per person
$1,090
per person
Apr 5 - Apr 9
found 23 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $1,972, price is now $1,444 per person
$1,444
per person
Apr 20 - Apr 24
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $1,535, price is now $1,162 per person
$1,162
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was $2,113, price is now $1,625 per person
$1,625
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Price was $1,794, price is now $1,386 per person
$1,386
per person
Apr 26 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3.5 out of 5
Price was $1,625, price is now $1,266 per person
$1,266
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Price was $1,699, price is now $1,335 per person
$1,335
per person
Apr 9 - Apr 13
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)

5-night Wailea vacations

Price found within the past 48 hours. Click for updated prices.
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,480, price is now $1,059 per person
$1,059
per person
Apr 28 - May 3
just found
Roundtrip non-stop 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
Price was $2,154, price is now $1,512 per person
$1,512
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 $2,094, price is now $1,486 per person
$1,486
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was $2,287, price is now $1,632 per person
$1,632
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $3,211, price is now $2,357 per person
$2,357
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $2,056, price is now $1,546 per person
$1,546
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $2,057, price is now $1,569 per person
$1,569
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was $2,768, price is now $2,164 per person
$2,164
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was $2,530, price is now $1,988 per person
$1,988
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3.5 out of 5
Price was $2,153, price is now $1,696 per person
$1,696
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Price was $2,300, price is now $1,818 per person
$1,818
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Price was $2,064, price is now $1,644 per person
$1,644
per person
Apr 5 - Apr 10
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)

6-7 night Wailea vacations

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

Kahana Villa

3 out of 5
Price was $1,912, price is now $1,408 per person
$1,408
per person
Apr 22 - Apr 29
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,764, price is now $1,842 per person
$1,842
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.5 out of 5
Price was $4,334, price is now $2,896 per person
$2,896
per person
Apr 22 - Apr 29
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $2,706, price is now $1,850 per person
$1,850
per person
Apr 27 - May 4
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $2,469, price is now $1,774 per person
$1,774
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $2,997, price is now $2,173 per person
$2,173
per person
Apr 23 - Apr 30
found 1 day ago
Roundtrip non-stop 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 $3,091, price is now $2,248 per person
$2,248
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 $4,467, price is now $3,271 per person
$3,271
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3.5 out of 5
Price was $2,492, price is now $1,857 per person
$1,857
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $3,369, price is now $2,523 per person
$2,523
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER

3 out of 5
Price was $2,378, price is now $1,792 per person
$1,792
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Kapalua Villas Maui

Kapalua Villas Maui

4 out of 5
Price was $2,517, price is now $1,903 per person
$1,903
per person
Apr 5 - Apr 12
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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
$139 Roundtrip, found 5 hours ago
$139
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Apr 25 from Oahu to Maui, returning Wed, Apr 29, priced at $139 found 5 hours ago
Mon, May 11 - Tue, May 12
HNL
Oahu
JHM
Kapalua
$151 Roundtrip, found 4 days ago
$151
Roundtrip
found 4 days ago
Select Southern Airways Express flight, departing Mon, May 11 from Oahu to Kapalua, returning Tue, May 12, priced at $151 found 4 days ago
Sun, May 10 - Wed, May 13
OAK
Oakland
OGG
Maui
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Sun, May 10 from Oakland to Maui, returning Wed, May 13, priced at $197 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
$995 nightly
The price is $1,181 total per night
$1,181 total
Apr 4 - Apr 5
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
$1,305 nightly
The price is $1,549 total per night
$1,549 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
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
$912 nightly
The price is $1,083 total per night
$1,083 total
Mar 22 - Mar 23
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.