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Kaupo Vacation Rentals

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Our top choices for Kaupo vacation rentals

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

Hana Town Center
9.6 out of 10, Exceptional, (413)
"Great stay. "
United States
Anthony A.
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Oceanview Condo in Hana-Let the ocean lull you to sleep

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

Stay in Hana #2

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

Fisher's Hana Bay Hale, Across from Hana Bay

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

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

Hana
10.0 out of 10, Exceptional, (247)
"What a beautiful quaint house with so much character and cute little antique accents. Hosts were great! Great communication and abundance of local insight. So peaceful with a secluded yard adorned with plumerias, orchids, palms and so much more. What a perfect little place to call home for 11 nights."
United States
DAWN L.
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Kipahulu
9.8 out of 10, Exceptional, (259)
"The place (and the view) was absolutely spectacular, peaceful and quite. Samadhi, the host, was very kind and helpful. We will never forget our time in Hana. Thank you!!! "
United States
Eva N.
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Stay in Hana #1

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

Exceptional Upcountry Villa with breathtaking views

Makawao
10.0 out of 10, Exceptional, (46)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
United States
Kimberly P.
Exceptional Upcountry Villa with breathtaking views

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Kula
10.0 out of 10, Exceptional, (185)
"Great stay"
United States
Peter A.
$863 nightly
The price is $1,005
Dec 10 - Dec 11
Total with taxes and fees
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Hana
10.0 out of 10, Exceptional, (185)
"Beautiful peaceful home. "
United States
Rebecca
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

Hana Town Center
10.0 out of 10, Exceptional, (19)
"Incredible property!!I would love to come back again. "
United States
Cynthia O.
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

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!

Secluded cottage on Tropical flower farm

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

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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!

Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Hana Town Center
10.0 out of 10, Exceptional, (70)
"Awesome place!"
United States
Darek and Brandi R.
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Hana Town Center
9.6 out of 10, Exceptional, (77)
"Great location! Was so nice to walk the grounds and the beach. Close to food trucks and black sand beach. Would definitely stay here again! "
United States
Nicole H.
$392 nightly
The price is $456
Dec 19 - Dec 20
Total with taxes and fees
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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!

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Hana Town Center
9.8 out of 10, Exceptional, (26)
"Great place, very convenient and amazing settings! "
United States
Dan R.
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Kaʻeleku
9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
$834 nightly
The price is $971
Dec 14 - Dec 15
Total with taxes and fees
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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
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

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.

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.