Search Deals onKaupakulua Vacation Packages
Kaupakulua Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Castle Kama'ole Sands
Price was $1,372, price is now $1,056 per person
$1,056
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pickleball courts. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.
We had everything we needed.
Reviewed on Sep 1, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Save 100% on your flight
Price was $9,133, price is now $5,756 per person
$5,756
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards!
Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches.
The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool!
The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X
Reviewed on Sep 6, 2026

Maui Beach Vacation Club
Price was $3,935, price is now $2,806 per person
$2,806
per person
Nov 20 - Nov 27
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Amazing location right across from the water. Gorgeous pool and spa. Room was bigger than expected and very clean. Brandi in the front office was amazing at check in and when I had more questions. Room had laundry and full kitchen, everything was so comfy. Would definitely stay here again.
Only con about this place was the woman with the barking dog and her attitude towards kids. She thought it was appropriate to play piano to “punish” the children for playing in the pool and making her dog bark. Piano playing was decent and I don’t think she punished anyone. It was wonderful background music and kids still played. It’s better to bring everyone together instead of being spiteful. Aloha!
Reviewed on Sep 9, 2026

Royal Lahaina Bungalows & Spa
Save 100% on your flight
Price was $1,973, price is now $1,445 per person
$1,445
per person
Nov 26 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village are located nearby.

Kauhale Makai - Maui Condo & Home
Price was $1,897, price is now $1,414 per person
$1,414
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this beach condo in Kihei. Enjoy free WiFi, a beach locale, and a sauna. Popular attractions Wailea Beach and Waipuilani Park are located nearby.
Beautiful room, spacious and comfortable
Reviewed on Nov 8, 2025

Palms at Wailea Maui
Price was $2,203, price is now $1,653 per person
$1,653
per person
Dec 3 - Dec 9
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this golf aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach South are located nearby.
We had an amazing time. We were close to the shops and beaches. The kids loved the pool and we had a beautiful view of the ocean. We would definitely stay there again.
Reviewed on Aug 12, 2026

Sugar Beach Resort - Maui Condo & Home
Price was $1,763, price is now $1,375 per person
$1,375
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this beach condo in Kihei. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the property condition in our reviews. Popular attractions Sugar Beach and Maalaea Bay Beaches are located nearby.
The property and condo were extremely clean and well maintained.
Reviewed on Aug 9, 2026

Maui Kamaole - Maui Condo & Home
Price was $1,658, price is now $1,293 per person
$1,293
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a garden. Popular attractions Wailea Beach and Kihei Boat Ramp are located nearby.
Kaupakulua Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Kaupakulua Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



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

Tue, Oct 6 - Tue, Oct 6
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, found 2 hours ago
$133
Roundtrip
found 2 hours ago

Sun, Sep 27 - Wed, Oct 7
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago

Mon, Nov 9 - Fri, Nov 13
OAK
Oakland Intl.
OGG
Kahului
$280 Roundtrip, found 23 hours ago
$280
Roundtrip
found 23 hours ago

Mon, Nov 2 - Tue, Nov 17
SFO
San Francisco Intl.
OGG
Kahului
$287 Roundtrip, just found
$287
Roundtrip
just found
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