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Kaupo Holiday Rentals

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Holiday Rentals in Kaupo

STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 292 reviews
"Amazing. thank you. "
STHA-2017/0002 Across from Hana Bay
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, 308 reviews
"We loved this place! Very homey and cute. Very easy to walk into town with beautiful views. The property has gorgeous landscaping and is well taken care of."
The price is NZ$645
per night
1 Jul - 2 Jul
Fisher's Hana Bay Hale, Across from Hana Bay
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, 241 reviews
"Loved the ocean view. Although our unit was old it was well kept and offered us every amenity."
Wailea Ekolu - CoralTree Residence Collection
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, 130 reviews
"Beautiful property in Wailea. We enjoyed the pool all day and Elaine was so sweet. Will stay here again."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, 226 reviews
"We loved our stay here. The place was very clean, and the scenery was stunning. It was a very relaxing and enjoyable place to stay. There were issues on the island with power going out due to a fallen tree in the forest, but the owners were very responsive to texts and even drove out to give us lanterns in case there was another outage. I highly recommend staying here!"
The price is NZ$906
per night
19 Jun - 20 Jun
Secluded cottage on Tropical flower farm
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
9.6 out of 10, Exceptional, 88 reviews
"This is a great property right on a black sand beach. The staff at Hana Kai are very helpful and friendly, and made our stay great. The condo we stayed in had a great view of the beach, was comfortable and is located in a great spot to get around easily."
The price is NZ$816
per night
20 Jun - 21 Jun
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, 193 reviews
"We had a wonderful experience."
The price is NZ$965
per night
17 Jun - 18 Jun
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
10.0 out of 10, Exceptional, 48 reviews
"Beautiful house, nice property, peaceful neighborhood, very clean, amazing scenery, close to everything, awesome host!"
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
10.0 out of 10, Exceptional, 199 reviews
"We were a large family but there was plenty of room for us all (10 and babies). The location was perfect for anywhere you wanted to go on the island and the house met the highest standards. We had everything we needed for cooking, for washing and for the beach. One hiccup was we lost air condenser the first day but the owner resolved it right away. Not a problem most would ever encounter. Oh, and we laughed at the goats, cows, and birds interacting next door. A calf was born the first day. And...
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
9.8 out of 10, Exceptional, 63 reviews
"Great property perfect for families. We loved it so much we actually extended our vacation and stayed an extra day. For sure will be repeat guests."
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
10.0 out of 10, Exceptional, 160 reviews
"So happy we found this wonderful spot so we could easily get to the Kipahulu side of the park. The owners/managers were so helpful in providing lots of information about Hana. The architecture of the house is really unique... we loved it!"
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
9.8 out of 10, Exceptional, 221 reviews
"The most magical stay imaginable! We loved the uniqueness of staying in a garden paradise. The gardens, views and cool breezes were amazing. We won’t forget this place anytime soon."
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Beautiful Home in paradise!
9.6 out of 10, Exceptional, 150 reviews
"Beyond expectations! Beautiful property,"
Beautiful Home in paradise!
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, 162 reviews
"Wonderful! Great location."
The price is NZ$828
per night
30 Jun - 1 Jul
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Great location between Hana Town and Hamoa Beach, private, family-friendly
9.8 out of 10, Exceptional, 208 reviews
"Nice small house just outside Hana, but close to everything. 1min to food trucks and stores, 5min to two beaches (and Huli Huli Chicken). It is a good place to start for day trips to do all the road to Hana things without hurry and be the first at Waimoku Falls, Waiʻānapanapa State Park or Lava Tube. If we (family of 4) come back to Hana, we happily would stay here again."
Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Bay Oceanfront Cottage
10.0 out of 10, Exceptional, 6 reviews
"My husband and I spent two weeks in Maui for his birthday and to get some R&R. Staying in Hana was at the top of our vacation list, and we spent quite a bit of time looking for top-notch lodging. This cottage was absolutely spectacular! The unobstructed views of the beach, the sounds of the surf, and the quiet neighborhood were beyond our expectations! We spent a lot of time on the lanai just watching the waves crash on the beach, reading our books, eating homemage meals.... it was so...
Hana Bay Oceanfront Cottage
Relaxing home away from home- honeymoon friendly
10.0 out of 10, Exceptional, 261 reviews
"The quintessential country cottage with a view that’s unmatched."
Relaxing home away from home- honeymoon friendly
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
9.8 out of 10, Exceptional, 173 reviews
"Views were good, however a lot of construction noise is going on right in front of the condo. Took away from the peacefulness of vacation. Absolutely no toiletries at all !"
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
Upcountry Kula - Private House On The Slopes Of Haleakala - Multi-Island View
10.0 out of 10, Exceptional, 151 reviews
"Amazing property!!! Hosts are super welcoming and our 2 kids very much enjoyed the chickens. The location in Upcountry is relaxing and the views are stunning. Easy access to all Maui had to offer. Property came with everything listed along with fresh eggs, juice, milk, and a fresh loaf of bread. We'll be returning to Maui and most likely staying here again. Cannot say how much we enjoyed our stay. It was like our home away from home."
Upcountry Kula - Private House On The Slopes Of Haleakala - Multi-Island View
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
9.8 out of 10, Exceptional, 158 reviews
"This is a solid five star review. The house is absolutely perfect and right on the water. The breeze is heavenly and the location couldn’t be better. It is a very nice home and extremely comfortable and well appointed in every way the back porch is fantastic for being outside as a group, the hot tub is a nice bonus and is also very nice. We would for sure like to return sometime."
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
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See all available 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.

Other types of properties in Kaupo you may be interested in

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
9.4 out of 10, Exceptional, 953 reviews
"Beautiful and quiet stay. I can’t wait to go back one day. "
The price is NZ$1,721
per night
15 Jun - 16 Jun
Hotel Wailea, Relais & Chateaux - Adults Only
Hana-Maui Resort, a Destination by Hyatt Residence
4.0 star property
9.0 out of 10, Wonderful, 892 reviews
"Loved the location, but property is a bit dated. Also, I had an activity booked and no hotel staff showed up to lead it. When I called the front desk, they said they'd ask their activity lead if anyone was coming and text me back. 30 min later I got a text that so activities that day were cancelled. That's a big reason why the resort was so appealing and they didn't even have the courtesy to tell me when I checked in and told them how excited I was for the activities (hula dancing, lei making,...
The price is NZ$1,097
per night
16 Jun - 17 Jun
Hana-Maui Resort, a Destination by Hyatt Residence
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, 130 reviews
"Beautiful property in Wailea. We enjoyed the pool all day and Elaine was so sweet. Will stay here again."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kaupo holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kaupo. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Kaupo. Seeing all the best attractions is bound to make you fall in love with Kaupo. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Kaupo short-term rentals, that won’t be hard to do.

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?

STHA-2017/0002 Across from Hana Bay: This holiday home rental outside of Kaupo is located in a rural location, and has a patio, 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. Kipahulu Visitor Center and Hana Forest Reserve 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.

Recent reviews of Kaupo properties
Expedia verified reviews