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Kaupo Holiday Rentals

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Holiday Rentals in Kaupo

Oceanview Condo in Hana-Let the ocean lull you to sleep
9.2 out of 10, Wonderful, (109)
"A good place to stay "
United States
Xiaohong
The price is NZ$686
includes taxes & fees
31 Oct - 1 Nov
Oceanview Condo in Hana-Let the ocean lull you to sleep
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
9.6 out of 10, Exceptional, (166)
"Stayed here for 9 days with my familyOf 4. More than enough space, photos don’t do it justice. Would stay here again"
United States
Jennifer T.
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
10.0 out of 10, Exceptional, (70)
"This property was indescribable! Our stay was amazing and the host was so very accommodating! Check-in was a breeze and every room was meticulously cleaned, arranged, and ready for our group. "
United States
James B.
The price is NZ$5,522
includes taxes & fees
17 Nov - 18 Nov
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, (261)
"It’s a great place to Stay for the family vacation."
Canada
Bhim Bahadur
Wailea Ekolu - CoralTree Residence Collection
Private lush 2 Acre Mountain Home Maui w/ many amenities
10.0 out of 10, Exceptional, (230)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
United States
Courtney P.
Private lush 2 Acre Mountain Home Maui w/ many amenities
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
9.6 out of 10, Exceptional, (403)
"We enjoyed our Stay, especially the near zu the entrance of the Volcano NP was really great."
Germany
Katja Monika B.
The price is NZ$619
includes taxes & fees
8 Nov - 9 Nov
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Exceptional Upcountry Villa with breathtaking views
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
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
9.8 out of 10, Exceptional, (255)
"My husband and I stayed for the last two days of our honeymoon. Relaxing and Romantic!! Hosts were amazing!"
United States
Hilary W.
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
10.0 out of 10, Exceptional, (181)
"Great stay"
United States
Peter A.
The price is NZ$1,878
includes taxes & fees
28 Oct - 29 Oct
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
10.0 out of 10, Exceptional, (181)
"We loved the home and enjoy the sound of nature. Well located, near Hamoa beach"
Canada
Pascale L.
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
9.8 out of 10, Exceptional, (158)
"This was a great place for all 8 of us to stay! We loved the pool and hot tub. It was a nice location to get to the places we visited."
United States
Diane C.
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Tropical stays where comfort meets the course
9.2 out of 10, Wonderful, (19)
"Great stay!"
United States
Carlos
Tropical stays where comfort meets the course
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (407)
"Wonderful property and a great place to stay in Hana"
United States
Daniel
The price is NZ$694
includes taxes & fees
31 Oct - 1 Nov
Fisher's Hana Bay Hale, Across from Hana Bay
Secluded cottage on Tropical flower farm
9.4 out of 10, Exceptional, (274)
"A wonderful place. Highly recomend"
United States
Alex s.
The price is NZ$960
includes taxes & fees
29 Oct - 30 Oct
Secluded cottage on Tropical flower farm
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
9.8 out of 10, Exceptional, (21)
"Great place, very convenient and amazing settings! "
United States
Dan R.
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
10.0 out of 10, Exceptional, (197)
"It’s like having your own resort"
United States
jennifer m.
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, (189)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is NZ$721
includes taxes & fees
31 Oct - 1 Nov
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Stay in Hana #2
9.6 out of 10, Exceptional, (40)
"We stayed over night there and it was amazing just right for a one night stay"
United States
christy h.
The price is NZ$602
includes taxes & fees
30 Oct - 31 Oct
Stay in Hana #2
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is NZ$1,514
includes taxes & fees
28 Oct - 29 Oct
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
10.0 out of 10, Exceptional, (50)
"Our family really enjoyed this log house. Beautiful property at the best time of the year. Host was super helpful with tips on activities and attractions."
United States
Daniel B.
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kaupo holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kaupo holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaupo holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaupo holiday rentals we have selected for you start as low as NZ$602 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kaupo rentals

At Expedia, we put the best Kaupo holiday 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 holiday.

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 holiday rentals in Kaupo?

Yes, there are holiday rentals close to the most popular sights in Kaupo, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kaupo has to offer?

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : This holiday home rental outside of Kaupo is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most 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. Bamboo Forest and Wailua Falls are a couple of places you'll find in the wider area.

What’s a holiday rental in Kaupo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaupo. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.