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

The Ocean View Residence
Price was $1,740, price is now $1,248 per person
$1,248
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Wailea Beach and Charley Young Beach are located nearby.

The Kalama Residence
Price was $5,790, price is now $3,389 per person
$3,389
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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

Signature Residences at Maui Banyan
Save 100% on your flight
Price was $1,819, price is now $1,304 per person
$1,304
per person
Nov 11 - Nov 18
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Book a stay at this business-friendly condo in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Amenities were complete. The host provided more than my expectations. Being close to the beach, chairs, umbrella, and beach towels were available.
Reviewed on Aug 22, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Save 100% on your flight
Price was $5,126, price is now $3,733 per person
$3,733
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Kamaole - Maui Condo & Home
Save 100% on your flight
Price was $1,963, price is now $1,456 per person
$1,456
per person
Nov 3 - Nov 10
found 19 hours ago
Roundtrip non-stop 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.

Maui Banyan - Maui Condo & Home
Save 100% on your flight
Price was $1,695, price is now $1,269 per person
$1,269
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a picnic area. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

Kauhale Makai - Maui Condo & Home
Save 100% on your flight
Price was $1,826, price is now $1,369 per person
$1,369
per person
Nov 3 - Nov 10
found 19 hours 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 $3,035, price is now $2,289 per person
$2,289
per person
Oct 19 - Oct 25
found 21 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
Kaupo Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Kaupo 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
$145 Roundtrip, just found
$145
Roundtrip
just found

Mon, Nov 9 - Fri, Nov 13
OAK
Oakland Intl.
OGG
Kahului
$287 Roundtrip, found 8 hours ago
$287
Roundtrip
found 8 hours ago

Mon, Oct 19 - Tue, Oct 27
SFO
San Francisco Intl.
OGG
Kahului
$305 Roundtrip, found 19 hours ago
$305
Roundtrip
found 19 hours ago

Tue, Nov 3 - Tue, Nov 17
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$315 Roundtrip, found 8 hours ago
$315
Roundtrip
found 8 hours ago
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