Kaupo Vacations from $966

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Your Kaupo Vacation

Enjoy amazing adventures when you lock in a Kaupo vacation package. Whether you're a foodie, history buff or just a traveler who loves discovering new places, there's something for everyone in this lively city. Any trip to Kaupo needs a well-planned itinerary. Fill yours with attractions like Bamboo Forest, Oheo Gulch and Pools of Oheo. Check out Expedia's extensive range of travel options and book your ideal vacation to Kaupo today.

The Latest Kaupo vacation packages

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
Price was $1,641, price is now $966 per person
$966
per person
Mar 8 - Mar 14
found 18 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (512 reviews)
Good amenities, good neighborhood. If you are willing to drive some distance then this place works great as you can walk to the Napili and Kapalua beaches.

Reviewed on Jan 5, 2026

Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,779, price is now $1,022 per person
$1,022
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (744 reviews)
We loved it definitely coming back !

Reviewed on Jan 20, 2026

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $2,772, price is now $1,640 per person
$1,640
per person
Mar 2 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9/10 Wonderful! (1,465 reviews)
The pool needs a makeover.

Reviewed on Jan 19, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $4,541, price is now $2,706 per person
$2,706
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Everything was exceptional! Great property, quiet and peaceful

Reviewed on Jan 6, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $1,905, price is now $1,164 per person
$1,164
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.2/10 Very Good! (814 reviews)
Very clean, great staff. Pool was nice, good location. Living room furniture uncomfortable.

Reviewed on Jan 16, 2026

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Discover the most popular places to visit in Kaupo

Keawaiki Bay from Waianapanapa State Park near Hana, Maui, Hawaii

Waianapanapa State Park

4.5/5(189 reviews)

If a restful vacation is part of your travel plans, Waianapanapa State Park might be the perfect place to seek out during your trip to Hana. Wander the seaside and gardens in this relaxing area.

Waianapanapa State Park
Waterfall, Hana, Maui, Hawaii, USA

Maui Garden Of Eden - Botanical Gardens & Arboretum

5/5(1 review)

Explore the great outdoors at Maui Garden Of Eden - Botanical Gardens & Arboretum, a lovely green space in Hana. Wander the beaches and seaside in this romantic area.

Maui Garden Of Eden - Botanical Gardens & Arboretum
Black Sand Beach State Park on the Hana Road, Maui, Hawaii

Black Sand Beach

Why not spend a lazy afternoon at Black Sand Beach during your trip to Hana?

Black Sand Beach

What to do in Kaupo

Kahului: Self-Driving Audio Tour of Road to Hana

Road to Hana Maui Tour: Self-Guided Audio Drive

$17
per traveler
86% of travellers recommend
Road to Hana Maui Tour: Self-Guided Audio Drive
Maui Horseback Adventure at Circle M Ranch With Real Cowboys

Maui Horseback Adventure at Circle M Ranch With Real Cowboys

$185
per adult
100% of travellers recommend
Maui Horseback Adventure at Circle M Ranch With Real Cowboys
Maui Sunriders Bike Co. 20 Years Providing Self-Guided Haleakala Downhill Bike Tours! Over 1000+ 5 star reviews! Maui's Best & Longest Ride over any operator, from the mountain to the sea.

Best Haleakala Downhill Self-Guided Bike Tour with Maui Sunriders

$139
per adult
80% of travellers recommend
Best Haleakala Downhill Self-Guided Bike Tour with Maui Sunriders
See all activities in Kaupo

Kaupo Hotel Deals

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
$633 nightly
The price is $751 total per night from Feb 21 to Feb 22
$751 total
Feb 21 - Feb 22
Total with taxes and fees
9/10 Wonderful! (999 reviews)
Pool was lovely. Staff responsive and professional. Accommodations could use some upgrading.

Reviewed on Jan 16, 2026

Hana-Maui Resort, a Destination by Hyatt Residence
Exceptional Upcountry Villa with breathtaking views

Exceptional Upcountry Villa with breathtaking views

Makawao HI
10/10 Exceptional! (47 reviews)
Absolutely stunning view. Well-stocked house. Hot tub is wonderful in the cooler winter mountain air.

Reviewed on Jan 1, 2026

Get rates
Exceptional Upcountry Villa with breathtaking views
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Hana HI
$304 nightly
The price is $356 total per night from Jan 24 to Jan 25
$356 total
Jan 24 - Jan 25
Total with taxes and fees
9.6/10 Exceptional! (418 reviews)
We really enjoyed our stay. It is an old home that has been converted to a VRBO. There were two beds inside, but we slept on the lanai. If you want modern, this isn’t the place. If you want to experience quiet Hāna, I would recommend it for your stay.

Reviewed on Jan 15, 2026

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
See all 84 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.

Find the Best Kaupo Vacation Packages

Kaupo Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)
Max Temp Winter
75ºF
Max Temp Summer
80ºF
Top Sights
Hamoa Beach, Red Sand Beach and Hana Lava Tubes

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Frequently asked questions

How much does a Kaupo vacation package cost?
You'll find cheap prices from $966 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 vacation to Kaupo costs.
What are the cheapest months to go to Kaupo?
You can typically find reduced prices and greater availability in October, November and December. Take a look at our cheap Kaupo vacation packages and you could score some great off-season deals.
How many days is enough for Kaupo?
With a well-planned schedule, you can easily hit the most popular Kaupo attractions in a handful of days. But if you want to discover hidden gems or take day trips, consider booking your Kaupo vacation 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 vacation package well in advance.
Is it cheaper to book a Kaupo vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations 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 vacation 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 your dates: What you'd like to do in Kaupo and your favorite season will help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will probably be the largest expense during your trip to Kaupo.
  3. Explore Kaupo with our trip planning tool: Gain insights into the top attractions and best properties for your trip to Kaupo. You can also save your favorite locations, collaborate with friends and family and manage all your plans in one place.
  4. Decide your trip length: Think about how long you'd like to spend discovering Kaupo. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Kaupo vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Kaupo's best offerings. Find all the fun things to do in Kaupo with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Kaupo vacation packages?
Secure your perfect trip to Kaupo with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.