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

Maui Banyan Vacation Club
Price was $1,557, price is now $1,149 per person
$1,149
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
The staff was very friendly and helpful. The room was not very clean.
Reviewed on Jul 21, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Save 100% on your flight
Price was $4,247, price is now $2,421 per person
$2,421
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip flight included
Nashville (BNA) 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.
This is a super nice adult only hotel. Nice and quiet. Staff is wonderful. On point. Hotel car service is excellent with luxury cars available. The room is nice. Large and spacious. My only critique is that the restaurant has a limited menu. But selection is great. Highly recommend.
Reviewed on Jul 25, 2026

Maui Beach Vacation Club
Price was $2,626, price is now $1,642 per person
$1,642
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. 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.

Lahaina Shores Beach Resort By Castle
Save 100% on your flight
Price was $2,092, price is now $1,317 per person
$1,317
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Kahului (OGG)
Book a stay at this beach apartment in Lahaina. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Kaanapali Beach and Whalers Village are located nearby.

Palms at Wailea Maui
Price was $1,695, price is now $1,216 per person
$1,216
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
The grounds are great and the staff was awesome. Sharee which I probably spelled wrong was awesome. We had some issue with our first unit and she immediately moved us to a new unit the next morning and was very helpful on any question we had or anything we needed. Just remember they are all
Individual owned so some are nice and some are not. That’s my only complaint I wish you could pick a unit other than just the size of it. Other the. That the pool is awesome. And the beach it literally a 5 minute walk down a small hill I have no idea where the people stayed tgat said it’s a long way away. We even had a very top unit closes to the entrance. Anyway great 2 weeks I would stay there again for sure very quiet area and close to everything.
Reviewed on Jul 21, 2026

Fairmont Kea Lani Maui
Price was $4,166, price is now $3,038 per person
$3,038
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.

The Residences at Kamaole Sands Resort
Save 100% on your flight
Price was $2,023, price is now $1,510 per person
$1,510
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this luxury aparthotel in Kihei. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.
The place was very clean. The staff was very communicative and accommodating. I stayed Wednesday-Sunday and I extended my stay 1 night which was very fast and easy. They left us chairs and towels which was very nice for the beach. The place was very spacious for 2 people. If you want to cook this has plenty of counter space. The balcony had a partial ocean view which was very nice. Great value for your money. Check in/out was very easy. You can walk right to the best beaches around.
Only Cons I can think of: Not a lot of blankets and the wifi in the bedroom didn’t really work, it was low signal. It would’ve been nice to watch Netflix from the bedroom. That’s the only negative I can think of.
Reviewed on Feb 24, 2026

Hale Akua Garden Farm & Eco-Retreat
Price was $1,774, price is now $1,354 per person
$1,354
per person
Oct 20 - Oct 26
found 20 hours ago
Roundtrip flight included
Nashville (BNA) to Kahului (OGG)
Stay at this country house in Haiku. Enjoy free WiFi, free parking, and 4 beach bars. Popular attractions Twin Falls and Garden of Eden Arboretum are located nearby.
Place was very serene. Such a cute hidden gem. Staff was very accommodating. Place was very clean. Loved the amenities!
Reviewed on Jul 14, 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
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Aug 26 - Wed, Aug 26
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$147 Roundtrip, just found
$147
Roundtrip
just found

Wed, Nov 11 - Wed, Nov 11
LAX
Los Angeles Intl.
OGG
Kahului
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago

Tue, Oct 20 - Tue, Oct 27
PDX
Portland Intl.
OGG
Kahului
$341 Roundtrip, found 4 hours ago
$341
Roundtrip
found 4 hours ago

Tue, Nov 17 - Sat, Dec 5
YVR
Vancouver Intl.
OGG
Kahului
$378 Roundtrip, found 3 days ago
$378
Roundtrip
found 3 days ago
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