Kaupo Holidays

Photo by Tim & Nat ✈

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Top hotels in Kaupo

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
Fully refundableReserve now, pay when you stay
The price is €948 per night from 14 Sept to 15 Sept
€948
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Book your next romantic getaway here
"The most amazing hotel you will ever stay at. The restaurant is fantastic. The hospitality is next level. The location is amazing. We truly had zero negatives. It’s expensive but worth it"

Reviewed on 19 Aug 2025

Hotel Wailea, Relais & Chateaux - Adults Only
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
5031 Hana Hwy, Hana, HI
Fully refundableReserve now, pay when you stay
The price is €515 per night from 23 Sept to 24 Sept
€515
23 Sept - 24 Sept
includes taxes & fees
9/10 Wonderful! (994 reviews)
"I loved the pool and yoga classes. It was the kind of place that the entire family loved. I was sorry I didn't book it for 2-3 nights. Helpful staff and beautiful grounds."

Reviewed on 19 Aug 2025

Hana-Maui Resort, a Destination by Hyatt Residence
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Makawao
The price is €2,643 per night from 10 Sept to 11 Sept
€2,643
10 Sept - 11 Sept
includes taxes & fees
10/10 Exceptional! (66 reviews)
50th anniversary family trip
"This is a beautiful property that easily and comfortably accommodated our family of 12. The large main house was perfect for gathering, with a spacious living room and well stocked kitchen. The grounds were gorgeous where the little ones loved running and playing, and a large pool and hot tub were ..."

Reviewed on 13 Aug 2025

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
See all 149 properties in Kaupo
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.

Popular places to visit

Maui Island featuring forests, a cascade and landscape views

Garden of Eden Arboretum

Follow walking trails to discover exotic plants and a century-old tree, enjoy picnics and take photos of a rock famous for appearing in a Hollywood movie.

Garden of Eden Arboretum
Koki Beach Park

Koki Beach Park

If a restful holiday is part of your travel plans, Koki Beach Park might be the perfect place to visit during your trip to Hana. Amble around this romantic area's seaside or seek out the yoga studios.

Koki Beach Park

Hanawi Natural Forest Reserve

Commune with nature and explore the great outdoors at Hanawi Natural Forest Reserve during your travels in Hana. Discover the sunrises in this relaxing area or seek out the yoga studios.

Hanawi Natural Forest Reserve

What to do in Kaupo

Private Waterfall, Rainforest & Handcrafted Chocolate Tour

Haiku: Waterfall, Rainforest, and Handcrafted Chocolate Tour

€111
per adult
100% of travellers recommend
Haiku: Waterfall, Rainforest, and Handcrafted Chocolate Tour
Road to Hana on Oahu

Day Trip to Heavenly Hana from Oahu

€453
per adult
90% of travellers recommend
Day Trip to Heavenly Hana from Oahu
Helicopter flying near sea cave in Hana

North Shore & Hana Rainforest Helicopter Tour with Taro Plantation Landing

€327
per adult
96% of travellers recommend
North Shore & Hana Rainforest Helicopter Tour with Taro Plantation Landing
See all activities in Kaupo

Frequently asked questions

How much does a Kaupo holiday package cost?
You'll find cheap prices on Expedia for your Kaupo break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your holiday to Kaupo costs.
What are the cheapest months to go to Kaupo?
January, February and June are the best times to look for cheap Kaupo holiday packages. Travelling in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Kaupo?
With a well-planned schedule, you can easily hit the most popular Kaupo sights in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Kaupo holiday for longer.
How to find the best Kaupo package deals?
Use Expedia's filters to find some tempting Kaupo package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Kaupo package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Kaupo holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights individually. Better still, you can tailor your Kaupo escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Kaupo?
If you're planning an impromptu Kaupo adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Kaupo?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to holiday in Kaupo.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Kaupo.
  3. Work out your trip length: Think about how much time you want to spend exploring Kaupo. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Kaupo holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.