Kaupakulua Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Kaupakulua holiday rentals

Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is S$442
includes taxes & fees
31 May - 1 Jun
Yonegan Maui Getaways - Haiku
Exterior

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (25 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
The price is S$680
includes taxes & fees
29 May - 30 May
Signature Residences at Maui Banyan
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is S$804
includes taxes & fees
29 May - 30 May
Kuau Plaza Paia Condo with Parking
Dining room

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is S$663
includes taxes & fees
3 Jun - 4 Jun
The Ocean View Residence
Interior

Stunning South Maui Condo w/ Lanai by Beach!

Stunning South Maui Condo w/ Lanai by Beach!
3.5 star property
North Kihei
The price is S$503
includes taxes & fees
22 Jun - 23 Jun
Stunning South Maui Condo w/ Lanai by Beach!
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (915 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
The price is S$469
includes taxes & fees
25 Jun - 26 Jun
Aston Maui Hill
On the beach, white sand

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 Kalama Residence
Terrace/patio

Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (4 reviews)
"Clean everything great time great location! "
United States
Sean
The price is S$3,800
includes taxes & fees
9 Jun - 10 Jun
Grand Champions by KBM
In-room dining

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (36 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is S$537
includes taxes & fees
5 Jun - 6 Jun
Kihei Ali'i Kai Condos with Free Parking
On the beach, white sand, beach towels

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)
"Grounds were beautiful. Beach view and access great. Quality of condo was in need of refreshing. Some broken doors, and in need of repair. The condo was clean."
United States
Eric
The price is S$590
includes taxes & fees
30 May - 31 May
Waiohuli Beach Hale Ocean View Condos with Parking
Beach/ocean view

Kamaole Sands Condos Close to Beach with Parking

Kamaole Sands Condos Close to Beach with Parking
3.5 star property
South Kihei
9.6 out of 10, Exceptional, (4 reviews)
"Clean property nice room good location"
United States
Richard
The price is S$698
includes taxes & fees
23 Jun - 24 Jun
Kamaole Sands Condos Close to Beach with Parking
Living area

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 S$901
includes taxes & fees
12 Jun - 13 Jun
2BR/2BA Oceanfront Condo in Maui Sunset
Outdoor dining

Polo Beach Club POL-109 by KBM

Polo Beach Club POL-109 by KBM
3.5 star property
Wailea
8.0 out of 10, Very good, (1 review)
"The property location was exactly what we wanted, easy access to the Wailea beachfront walking path and directly on the beach. We had a great time but if you are considering this place you need to go in with your eyes wide open. It was very pricey for how tired this unit is. It badly needs a full renovation. The tile is from the 1980's, the carpet is gross and crunchy. When we arrived late, it appeared someone had tried to break in the sliding doors and that set off numerous R&M emails...
Canada
PAMELA
The price is S$7,766
includes taxes & fees
12 Jun - 13 Jun
Polo Beach Club POL-109 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kaupakulua Hotel Reviews

Aston Maui Hill

Aston Maui Hill

10/10 Excellent
"The property was lovely. There are beautiful trees and flowers everywhere and gardeners. The condo was super. It had a beautiful lanai off the back that overlook the gardens! It was all very private. We really like the living room. The decor was nice. It had warm and comfortable surroundings and comfortable funiture. You felt very much at home. We had a two bedroom for the two of us. We loved it and it was very close to the beach that was down the street and trun left till the road stops… there are parking places at the beach or alongside the road which was very nice. You could go snorkeling out there or swim out and do whatever you want to do like bodysurf. It was a very private beach amongst beautiful homes. When we come back, we will definitely stay at the condo! Oh yes, and the swimming pool and hot tub was great and the beautiful pool had very soft water! The office had two concierge who will be happy to help you with any tours or places to eat on the island. We drove up to the volcano and that was a fabulous drive it is over 10,000 feet high from the beach. The office staff and cleaning staff was so very kind and helpful and they made it a treat to be there! Aloha and happy travels to you all! Leigh"
Ralph L. 8-night trip
Posted 7 hours ago
Aston Maui Hill

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. Maui Spa Retreat and Hoʻokipa Beach Park 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.