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Paia Vacation Packages

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Paia Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Castle at Maui Banyan

Castle at Maui Banyan

3.5 out of 5
Price was $1,722, price is now $741 per person
$741
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this hotel in Kihei. Enjoy free WiFi, free parking, and a garden. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
All good but our cheap jazz got the small room with two beds and it was small room for sure

Reviewed on Nov 6, 2026

Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Price was $4,105, price is now $2,458 per person
$2,458
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 restaurants, and 3 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.

Grand Champions

Grand Champions

2.5 out of 5
Price was $3,369, price is now $2,149 per person
$2,149
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this golf resort in Kihei. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
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Reviewed on Sep 30, 2026

The Kalama Residence

The Kalama Residence

3 out of 5
Price was $4,485, price is now $3,103 per person
$3,103
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Seattle (SEA) 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 Cove Park are located nearby.
The property was clean and nice. It did need some maintenance, but it was in good condition for its age. We liked how it was stocked to make our stay more comfortable.

Reviewed on Jan 4, 2026

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
Price was $2,755, price is now $1,931 per person
$1,931
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach North are located nearby.
Very clean and well maintained. Friendly staff.

Reviewed on Nov 7, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Price was $3,524, price is now $2,491 per person
$2,491
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. 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.
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Reviewed on Nov 7, 2026

Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was $1,295, price is now $916 per person
$916
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this boutique hotel in Makawao. Enjoy free breakfast, onsite spa services, and a garden. Popular attractions Haliʻimaile Farmer's Market and Maui Gold Pineapple Farm are located nearby.

Kihei Akahi - Maui Condo & Home

Kihei Akahi - Maui Condo & Home

2.5 out of 5
Price was $2,649, price is now $1,876 per person
$1,876
per person
Jan 9 - Jan 15
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and laundry facilities. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
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Reviewed on Sep 26, 2026

Paia Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was $1,295, price is now $916 per person
$916
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Price was $4,105, price is now $2,458 per person
$2,458
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
The Ocean View Residence

The Ocean View Residence

3 out of 5
South Kihei
Price was $2,219, price is now $1,508 per person
$1,508
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Price was $3,094, price is now $2,119 per person
$2,119
per person
Jan 7 - Jan 11
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)

Paia Vacation Packages 5-7 Night Stays

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 $1,802, price is now $1,069 per person
$1,069
per person
Jan 20 - Jan 26
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $2,036, price is now $1,138 per person
$1,138
per person
Jan 20 - Jan 26
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Price was $4,885, price is now $2,823 per person
$2,823
per person
Jan 20 - Jan 26
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was $2,377, price is now $1,453 per person
$1,453
per person
Jan 9 - Jan 16
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)

Top Flight Deals

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

Alaska Airlines
Tue, Jan 12 - Tue, Feb 2
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Jan 12 from Daniel K. Inouye Intl. to Kahului, returning Tue, Feb 2, priced at $138 just found
Southern Airways Express
Thu, Nov 26 - Fri, Nov 27
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select Southern Airways Express flight, departing Thu, Nov 26 from Daniel K. Inouye Intl. to West Maui, returning Fri, Nov 27, priced at $238 found 2 days ago
Bargain Flight
Fri, Nov 27 - Thu, Dec 17
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$323 Roundtrip, just found
$323
Roundtrip
just found
Select Bargain Flight flight, departing Fri, Nov 27 from Norman Y. Mineta San Jose Intl. to Kahului, returning Thu, Dec 17, priced at $323 just found
Bargain Flight
Tue, Jan 5 - Fri, Jan 22
OAK
Oakland Intl.
OGG
Kahului
$329 Roundtrip, just found
$329
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Jan 5 from Oakland Intl. to Kahului, returning Fri, Jan 22, priced at $329 just found