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Kaupo Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Kaupo vacation rentals

Beach
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Cottage in Hana Town Center

9.6 out of 10, Exceptional, (190)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
$399 nightly
The price is $464
Dec 16 - Dec 17
Total with taxes and fees
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beach towels
Fisher's Hana Bay Hale, Across from Hana Bay

Vacation Home in Hana Town Center

9.6 out of 10, Exceptional, (409)
"Cute place with character in Hana. It was so nice to not rush the road to Hana and stay in this remote location. "
United States
Annette M.
$340 nightly
The price is $398
Jan 8 - Jan 9, 2026
Total with taxes and fees
Fisher's Hana Bay Hale, Across from Hana Bay
Living area
Stay in Hana Upstairs

Apartment in Hana Town Center

9.8 out of 10, Exceptional, (33)
"Lovely place in a lush jungle. "
United States
Heather T.
$405 nightly
The price is $472
Dec 14 - Dec 15
Total with taxes and fees
Stay in Hana Upstairs
Outdoor dining
Oceanview Condo in Hana-Let the ocean lull you to sleep

Apartment in Hana Town Center

9.2 out of 10, Wonderful, (115)
"A good place to stay "
United States
Xiaohong
$395 nightly
The price is $460
Dec 14 - Dec 15
Total with taxes and fees
Oceanview Condo in Hana-Let the ocean lull you to sleep
Exterior
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!

Apartment in Hana Town Center

8.8 out of 10, Excellent, (35)
"Clean, comfortable room with a wonderful view in Hana!"
United States
Amelia
$363 nightly
The price is $423
Dec 14 - Dec 15
Total with taxes and fees
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!
Property grounds
Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!

Condo in Hana Town Center

9.4 out of 10, Exceptional, (61)
"Very cute place with ocean views!"
United States
Heather B.
$387 nightly
The price is $451
Dec 10 - Dec 11
Total with taxes and fees
Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!
On the beach
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Condo in Hana Town Center

9.6 out of 10, Exceptional, (23)
"I would stay again "
United States
Bruce H.
$363 nightly
The price is $423
Dec 12 - Dec 13
Total with taxes and fees
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Sun loungers, beach towels
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Vacation Home in Hana Town Center

9.2 out of 10, Wonderful, (145)
"We had a really nice stay at the Hana Bay View. The property had a really updated bathroom and good kitchen appliances. The covered deck was the best for winding down in the evening after all of our fun hiking and beach excursions! The AC in the bedrooms was a huge bonus. I highly recommend this place."
United States
Ross C.
$436 nightly
The price is $508
Dec 17 - Dec 18
Total with taxes and fees
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Exterior
Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!

Apartment in Hana Town Center

9.6 out of 10, Exceptional, (60)
"Great place walks on the black sand beach right out your door. Great food truck park a short distance away. It met all our needs"
United States
Kyle M.
$349 nightly
The price is $406
Dec 10 - Dec 11
Total with taxes and fees
Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!
Outdoor dining
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Condo in Hana Town Center

9.6 out of 10, Exceptional, (111)
"Everything Good "
United States
Marc
$460 nightly
The price is $535
Dec 20 - Dec 21
Total with taxes and fees
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Outdoor dining
Secluded cottage on Tropical flower farm

Cottage in Kaʻeleku

9.4 out of 10, Exceptional, (281)
"This was a great location, comfortable cute little cottage."
United States
Briana B.
$474 nightly
The price is $552
Dec 12 - Dec 13
Total with taxes and fees
Secluded cottage on Tropical flower farm
Property grounds
Stay in Hana #2

Apartment in Hana Town Center

9.6 out of 10, Exceptional, (43)
"Staying here was a pleasure - from the ease of the check in process, to the cleanliness of the room, amenities and location, we're so glad we chose this home!"
United States
Jenny E.
$295 nightly
The price is $344
Dec 13 - Dec 14
Total with taxes and fees
Stay in Hana #2
Fridge, microwave, oven, stovetop
Hana Homestead by the Beach

Vacation Home in Hana Town Center

9.8 out of 10, Exceptional, (136)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
United States
Christopher
$1,149 nightly
The price is $1,242
Dec 18 - Dec 19
Total with taxes and fees
Hana Homestead by the Beach
Property grounds
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

Apartment in Hana Town Center

9.8 out of 10, Exceptional, (83)
"The location was very good."
United States
Jim B.
$354 nightly
The price is $412
Dec 10 - Dec 11
Total with taxes and fees
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Outdoor dining
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Vacation Home in Kaʻeleku

9.8 out of 10, Exceptional, (235)
"Great property and excellent location with a perfect balance between privacy and proximity to Hana. "
United States
Michael T.
$553 nightly
The price is $644
Dec 11 - Dec 12
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Property grounds
Stay in Hana #1

Apartment in Hana Town Center

9.0 out of 10, Wonderful, (59)
"It was a very beautiful and clean property. I would definitely stay here again. I love the modern amenities and the decor. I loved where it was situated. It felt like we were in the middle of a rainforest."
United States
ROWENA
$296 nightly
The price is $345
Dec 11 - Dec 12
Total with taxes and fees
Stay in Hana #1
Property grounds
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Condo in Hana Town Center

9.6 out of 10, Exceptional, (75)
"Loved it!"
United States
Shon P.
$368 nightly
The price is $429
Dec 11 - Dec 12
Total with taxes and fees
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Living area
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Condo in Hana Town Center

9.6 out of 10, Exceptional, (76)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
$408 nightly
The price is $475
Dec 19 - Dec 20
Total with taxes and fees
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Property grounds
Oceanfront #2 at Hana Kai Maui - Romantic Studio 100' from Water!

Condo in Hana Town Center

9.6 out of 10, Exceptional, (25)
"Enjoyed the stay!"
United States
Tim D.
$406 nightly
The price is $473
Dec 12 - Dec 13
Total with taxes and fees
Oceanfront #2 at Hana Kai Maui - Romantic Studio 100' from Water!
Property grounds
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Condo in Hana Town Center

9.4 out of 10, Exceptional, (62)
"Everything was perfect!!!! We even had ice cold water waiting on us in the fridge!!! The condo was gorgeous, loved the kitchen! We could see the black sand beach from our gorgeous deck!!! My only regret was not staying longer!!!! I recommend the restaurant in Hana for dinner, it was excellent! We will be back!"
United States
Brenda
$349 nightly
The price is $406
Dec 11 - Dec 12
Total with taxes and fees
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
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.
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Top Kaupo Hotel Reviews

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

10/10 Excellent
"Terry was very kind and attentive. We felt like we were being hosted by family."
Joe W. 2-night trip
Posted 3 days ago
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens

Find out more about Kaupo

Everything you need to know about Kaupo vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kaupo vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kaupo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kaupo vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kaupo. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kaupo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $344 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kaupo rentals

At Expedia, we put the best Kaupo vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kaupo rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kaupo vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kaupo. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Kaupo?

Yes, we give you a choice of vacation rentals near well known local attractions in Kaupo, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental that Kaupo has to offer?

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : Visitors like this Kaupo vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Kaupo?

Explore the area and family-friendly sights such as Waikamoi Preserve, or get out into nature at a spot like Haleakala National Park. Haleakalā Visitor Center and Haleakala Crater are a couple of places you'll find in the larger area.

What’s a vacation rental in Kaupo like?

A vacation rental is a private property you can book for a couple of days or more in Kaupo. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.