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Kaupakulua Holiday Rentals

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Our top choices for Kaupakulua holiday rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is NZ$535
includes taxes & fees
14 Oct - 15 Oct
Yonegan Maui Getaways - Haiku

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is NZ$2,218
includes taxes & fees
31 Oct - 1 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

3. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NZ$1,721
includes taxes & fees
13 Oct - 14 Oct
Kuau Plaza Paia Condo with Parking

4. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (990 reviews)
"Way more than what we expected.. clean, well kept, extremely spacious and centrally located to shops, beaches and restaurants. Loved everything about the property"
United States
Michael
The price is NZ$634
includes taxes & fees
8 Nov - 9 Nov
Aston Maui Hill

5. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (40 reviews)
"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."
United States
Mai
The price is NZ$991
includes taxes & fees
11 Oct - 12 Oct
Signature Residences at Maui Banyan

6. The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas"
United States
George Lucas
The price is NZ$1,095
includes taxes & fees
14 Oct - 15 Oct
The Residences at Kamaole Sands Resort

7. Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (5 reviews)
"Clean everything great time great location! "
United States
Sean
The price is NZ$1,818
includes taxes & fees
12 Oct - 13 Oct
Grand Champions by KBM

8. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.4 out of 10, Exceptional, (3 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is NZ$1,181
includes taxes & fees
11 Oct - 12 Oct
The Ocean View Residence

9. Wonderful South Maui Beach Condos

Wonderful South Maui Beach Condos
3.5 star property
South Kihei
9.2 out of 10, Wonderful, (44 reviews)
"Great location, perfect for my trip. "
United States
John
The price is NZ$874
includes taxes & fees
2 Nov - 3 Nov
Wonderful South Maui Beach Condos

10. The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
The price is NZ$1,584
includes taxes & fees
16 Oct - 17 Oct
The Kalama Residence

11. South Maui Beach Suites

South Maui Beach Suites
3.5 star property
South Kihei
The price is NZ$858
includes taxes & fees
1 Nov - 2 Nov
South Maui Beach Suites

12. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
3.0 star property
Paia
The price is NZ$745
includes taxes & fees
18 Oct - 19 Oct
Condo w/ Lanai at Beginning of Road to Hana!

13. Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
The price is NZ$973
includes taxes & fees
22 Oct - 23 Oct
Waiohuli Beach Hale Ocean View Condos with Parking

14. Awesome Maui Vista Beach Suite

Awesome Maui Vista Beach Suite
4.0 star property
South Kihei
8.6 out of 10, Excellent, (27 reviews)
"Absolutely perfect!!! Flavor of Hawaii!!"
United States
Laura
The price is NZ$889
includes taxes & fees
1 Nov - 2 Nov
Awesome Maui Vista Beach Suite

15. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is NZ$2,962
includes taxes & fees
12 Oct - 13 Oct
Villa, Garden View, 2-bedroom

16. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (54 reviews)
"Absolutely an amazing place. Very nice, clean, comfortable. We stayed in B104 and it is a perfect spot to get in and out. Definitely come back again."
United States
Angeline
The price is NZ$899
includes taxes & fees
11 Oct - 12 Oct
Kihei Ali'i Kai Condos with Free Parking

17. 2BR/2BA Oceanfront Condo in Maui Sunset

2BR/2BA Oceanfront Condo in Maui Sunset
3.5 star property
Central Kihei
8.0 out of 10, Very good, (1 review)
The price is NZ$1,846
includes taxes & fees
15 Oct - 16 Oct
2BR/2BA Oceanfront Condo in Maui Sunset

18. Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
The price is NZ$887
includes taxes & fees
15 Oct - 16 Oct
Lanai & Steps to Beach! Stunning South Maui Condo

19. Wailea Beach Villas Resort by KBM

Wailea Beach Villas Resort by KBM
4.0 star property
Wailea
The price is NZ$7,644
includes taxes & fees
16 Oct - 17 Oct
Wailea Beach Villas Resort by KBM

20. Wailea Ekahi Village WKV-45C by KBM

Wailea Ekahi Village WKV-45C by KBM
4.5 star property
Wailea
6.0 out of 10, (1 review)
"I did not like this location and would not go back. It’s on a lower floor, and kind of dark and musty. I left within a few hours of being there. But the host was very communicative and the location is great. I just wouldn’t personally stay here."
United States
Chelsea
The price is NZ$2,095
includes taxes & fees
15 Oct - 16 Oct
Wailea Ekahi Village WKV-45C by KBM
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 Kaupakulua Hotel Reviews

Find out more about Kaupakulua

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 Kaupakulua 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 Kaupakulua. 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 Kaupakulua. Seeing all the best attractions is bound to make you fall in love with Kaupakulua. 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 Kaupakulua short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Kaupakulua?

Yes, there are holiday rentals close to the most popular sights in Kaupakulua, 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 Kaupakulua has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kaupakulua is located near the beach, and has 1 hot tub, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker and kitchenware.

What’s there to see and do in Kaupakulua?

While exploring the area, visit family-friendly sights like Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters, or get outside and enjoy nature at Haleakala National Park. Makawao Park and Maui Spa Retreat are a couple of places you'll find in the wider area.

What’s a holiday rental in Kaupakulua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaupakulua. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.