
Kaupo Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Kaupo vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.0-star property
Maui Banyan Vacation Club
8/10 Very Good! (346 reviews)
Dec 1 - Dec 6
5 night stay
Denver (DEN) to Kahului (OGG)
Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,369, price is now $802 per person
$802
per person
found 1 day ago
Property was exceptionally clean and welcoming. People at the poolside were nice. Pool was never crowded. The room I had was managed by Soliel and was impeccably clean, including the exhaust fan cover in the bathroom. I have never seen that anywhere before in all my travels. The property was beautiful and having free parking was a great amenity.
Reviewed on Feb 12, 2023

3.5-star property
OUTRIGGER Kaanapali Beach Resort
9/10 Wonderful! (1,336 reviews)
Nov 4 - Nov 8
4 night stay
Denver (DEN) to Kahului (OGG)
Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,452, price is now $852 per person
$852
per person
found 1 day ago
The Outrigger was an amazing place to stay. We walked out the door and to the beach about 100 yards away. We went snorkeling right off the beach and saw turtles, and so many beautiful fish and coral. The people who ran the Outrigger had many complimentary, fun things to do at the hotel every day, like weaving baskets, hula dancing lessons, and learning to play different instruments.
All of the people working there were very friendly and helpful. If we have the chance to go back to Maui, we would definitely stay there again.
Reviewed on Jun 16, 2025

5.0-star property
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
9.4/10 Exceptional! (1,001 reviews)
Dec 7 - Dec 11
4 night stay
Denver (DEN) to Kahului (OGG)
Delta • Non-stop • Coach
Kahului (OGG) to Denver (DEN)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,845, price is now $1,778 per person
$1,778
per person
found 1 day ago
Very serene, not crowded and no children. Perfect for an intimate getaway.
Reviewed on Mar 22, 2025

5.0-star property
Fairmont Kea Lani Maui
Wailea
9.4/10 Exceptional! (1,010 reviews)
Dec 7 - Dec 11
4 night stay
Denver (DEN) to Kahului (OGG)
Delta • Non-stop • Coach
Kahului (OGG) to Denver (DEN)
Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,881, price is now $1,819 per person
$1,819
per person
found 1 day ago
Easily some of the best service at any resort we’ve ever stayed. Start to finish everyone was fantastic. Front desk. Valet. Pool. Restaurants. Everyone went above and beyond. Will definitely return.
Reviewed on May 29, 2024

3.0-star property
Kahana Beach Vacation Club
8.4/10 Very Good! (714 reviews)
Nov 4 - Nov 8
4 night stay
Denver (DEN) to Kahului (OGG)
Alaska Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,428, price is now $929 per person
$929
per person
found 1 day ago
Highly recommended! Gorgeous ocean views, clean room, nice staff.
Reviewed on Sep 7, 2025
Top rated hotels for your Kaupo vacation package

Hana-Maui Resort, a Destination by Hyatt Residence
5031 Hana Hwy, Hana, HI
Free Cancellation
Reserve now, pay when you stay
11.88 mi from city center
$584 nightly
The price is $689 total per night
$689 total
Oct 30 - Oct 31
Total with taxes and fees
Guests of Hana-Maui Resort, a Destination by Hyatt Residence have access to a full-service spa, 2 outdoor pools, and a gym. If you drive, self parking is USD 15 per night, and there's also a free beach shuttle. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this spa resort include a sauna, free WiFi in public areas, and conference space.
Pool
Spa

Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street, Kihei, HI
Free Cancellation
Reserve now, pay when you stay
20.02 mi from city center
$999 nightly
The price is $1,178 total per night
$1,178 total
Oct 19 - Oct 20
Total with taxes and fees
Hotel Wailea, Relais & Chateaux - Adults Only features an outdoor pool, a gym, and a conference center. Parking is available for USD 36.65 per night (USD 36.65 per night for valet parking), and there's also an area shuttle. Multilingual staff at the 24-hour front desk can assist with securing valuables, concierge services, and luggage storage. Other amenities at this adults-only resort include a business center, coffee/tea in a common area, and free newspapers.
Pool
Spa
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.
Explore More Ways to Travel with Travelocity
Explore More Ways to Travel with Travelocity
- 3 Star Hotels in Upcountry Maui
- Farmstay in Upcountry Maui
- Cottages in Upcountry Maui
- Extended Stay Hotels in Upcountry Maui
- Guest Houses in Upcountry Maui
- Hostels in Upcountry Maui
- Boutique Hotels in Upcountry Maui
- Cheap Hotels in Upcountry Maui
- Kid Friendly Hotels in Upcountry Maui
- Hotels with Pool in Upcountry Maui
- Hotels with Bar in Upcountry Maui
- Hotels with Free Breakfast in Upcountry Maui
- Pet Friendly Hotels in Upcountry Maui
- Upcountry Maui Hotels
- Vacation Homes in Upcountry Maui
- Resorts in Upcountry Maui
- Villas in Upcountry Maui
- Hotels near Kalahaku Overlook
- Hotels near Haleakala Crater
- Hotels near Puʻuʻulaʻula
- Hotels near Bamboo Forest
- Hotels near Hana Lava Tubes
- Hotels near Koki Beach Park
- Hotels near Haleakalā Visitor Center
- B&B in Kipahulu
- Cottages in Kipahulu
- Kipahulu Hotels
- Vacation Homes in Kipahulu
- Hotels near Hamoa Beach
- Hotels near Waikamoi Preserve
- Hotels near Science City
- Hotels near Kipahulu Visitor Center
- Hana Forest Reserve Hotels
- Hotels near Charles Lindbergh's Grave
- Hotels near Hanawi Falls
- Hotels near Leleiwi Overlook
- 3 Star Hotels in Puuiki
- 4 Star Hotels in Puuiki
- 5 Star Hotels in Puuiki
- Cottages in Puuiki
- Guest Houses in Puuiki
- Hotels near The Skyline Trail
- Hotels near Haleakala National Park
- Hotels near Magnetic Peak
- Hotels near Hana Coast Gallery
- Apartments in Hana
- Cabin Rentals in Hana
- Condo Rentals in Hana
- Cottages in Hana
- Guest Houses in Hana
- Hana Hotels
- Vacation Homes in Hana
- Resorts in Hana
- Treehouses in Hana
- Condo Rentals in Haou
- Haou Hotels
- Flights from Upcountry Maui
- Flights from Newark to Upcountry Maui
- Flights to Maui
- Flights from Honolulu to Maui
- Flights from Seattle to Maui
- Flights to Hawaii
- Flights from Kipahulu
- Flights from Puuiki
- Flights from Honolulu to Hana
- Flights from Maui to Hana
- Flights from Kapalua to Hana
- Flights from Haou
- Haiku Vacations
- Mauiwine
- Wailea Emerald Golf Course
- Haleakala Bike Company
- Hanawi Natural Forest Reserve
- Maui Vacations
- Hana Lava Tubes
- Maui Garden Of Eden - Botanical Gardens & Arboretum
- Kula Vacations
- Keokea Vacations
- Wailea Vacations
- Koki Beach Park
- Kamaole Beach Park 3
- Hamoa Beach
- Hoʻomana Spa Maui
- Nanu'alele Point Beach
- Hana Bay Beach Park
- Kalaloa Point
- Maui Agricultural Research Center
- Kailua Vacations
- Aliʻi Kula Lavender
- Makawao Vacations
- Hanawi Falls
- Kihei Regional Park
- Makena State Park Beach
- Maluaka Beach
- Makena Vacations
- Kokomo Vacations
- Maui Nui Golf Club
- Hana Vacations