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Kaupakulua Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Kaupakulua holiday rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

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 AU$422
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

2. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
The price is AU$430
includes taxes & fees
30 Sept - 1 Oct
Yonegan Maui Getaways - Haiku - Unit 6
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

3. Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (22 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is AU$475
includes taxes & fees
24 Sept - 25 Sept
Yonegan Maui Getaways - Haiku - Unit 4
A wooden staircase leading to a balcony of a blue building surrounded by lush greenery and flowering plants.

4. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.2 out of 10, Wonderful, (23 reviews)
"Perfect getaway for an island vacation if your not planning on staying in just your room. Made breakfast every morning close to beaches, turtles and shops"
United States
Jeremiah J.
The price is AU$422
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku - Unit 3
A beach with clear blue water, rocky shore, and palm trees.

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

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"This was the perfect stay to start the Road to Hana and the town of Paia is so lovely and had a lot of food options. The beaches around this area were some of our favorite. If you can, make a reservation at Mamas Fishhouse or try and walk in around lunch time-it’s worth every penny! "
United States
Kiana C.
The price is AU$580
includes taxes & fees
5 Oct - 6 Oct
Condo w/ Lanai at Beginning of Road to Hana!
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

6. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AU$648
includes taxes & fees
25 Sept - 26 Sept
Hale Nihi - Paia, Maui
A living room with a sofa, a coffee table, a TV, and a sliding glass door leading to a patio with a view of palm trees and a lawn.

7. Eco-Friendly Condo on Road to Hāna - Walk to Beach

Eco-Friendly Condo on Road to Hāna - Walk to Beach
Paia
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is AU$586
includes taxes & fees
27 Sept - 28 Sept
Eco-Friendly Condo on Road to Hāna - Walk to Beach
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

8. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (39 reviews)
"It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose"
United States
Roark
The price is AU$795
includes taxes & fees
27 Sept - 28 Sept
Signature Residences at Maui Banyan
An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

9. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is AU$696
includes taxes & fees
30 Sept - 1 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
A living room with a sofa, coffee table, and a large mirror. There is a sliding glass door leading to an outdoor area with a table and chairs.

10. Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (47 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is AU$593
includes taxes & fees
30 Sept - 1 Oct
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
A balcony with a table set for two, featuring a bottle of wine and two glasses.

11. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (308 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
The price is AU$540
includes taxes & fees
24 Sept - 25 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

12. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (531 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
The price is AU$545
includes taxes & fees
26 Sept - 27 Sept
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A beach with clear blue water, a sandy shore, and a distant mountain.

13. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (85 reviews)
"We loved our stay! Great location"
United States
Madison
The price is AU$474
includes taxes & fees
2 Oct - 3 Oct
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
A hotel with a pool area, beach view, and palm trees.

14. SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
9.4 out of 10, Exceptional, (78 reviews)
"Excellent ground floor condo with easy access to the pool and beach. Clean, cozy, and comfortable with everything we needed including a washer and dryer, lots of beach chairs and beach towels and really nice staff. The grounds at the resort are beautiful and we loved the hot dry sauna and the jacuzzi! We will definitely stay here again!"
United States
Jodelle F.
The price is AU$653
includes taxes & fees
26 Sept - 27 Sept
SUMMER RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
A table with a bottle and glasses on a red mat, surrounded by red chairs on a balcony with a view of palm trees and a tennis court.

15. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (280 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is AU$540
includes taxes & fees
24 Sept - 25 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
An aerial view of a resort with a beach, a swimming pool, and palm trees.

16. BEACHFRONT PROPERTY at Kihei Sands - A13

BEACHFRONT PROPERTY at Kihei Sands - A13
North Kihei
9.8 out of 10, Exceptional, (72 reviews)
"Nice property, beautiful beach with views of the sunset."
United States
Adrienne P.
The price is AU$739
includes taxes & fees
24 Sept - 25 Sept
BEACHFRONT PROPERTY at Kihei Sands - A13
An aerial view of a resort with a beach, a swimming pool, and palm trees.

17. OCEANFRONT RESORT - Last-Minute Getaway Summer/Fall Rates! Kihei Sands - B14

OCEANFRONT RESORT - Last-Minute Getaway Summer/Fall Rates! Kihei Sands - B14
North Kihei
9.8 out of 10, Exceptional, (107 reviews)
"Great location. Staff was outstanding. The condo was as advertised and we were very impressed with how spotless everything was."
United States
Gary R.
The price is AU$907
includes taxes & fees
29 Sept - 30 Sept
OCEANFRONT RESORT - Last-Minute Getaway Summer/Fall Rates! Kihei Sands - B14
A tropical garden with a small pond, lush greenery, and a staircase leading to an upper level.

18. Beautiful Beach Chic Condo, Large Lanai, Beach Across Street!

Beautiful Beach Chic Condo, Large Lanai, Beach Across Street!
North Kihei
9.6 out of 10, Exceptional, (37 reviews)
"Great stay! Had equipment for us to enjoy the beaches which was unexpected but lovely! Would stay again. "
United States
Miguel B.
Beautiful Beach Chic Condo, Large Lanai, Beach Across Street!
A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

19. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (317 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
The price is AU$554
includes taxes & fees
30 Sept - 1 Oct
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
A beach with a palm tree, rocky shoreline, and a wooden bench.

20. FALL IN MAUI!!! Perfect Island Getaway

FALL IN MAUI!!! Perfect Island Getaway
South Kihei
9.6 out of 10, Exceptional, (26 reviews)
"Absolutely fantastic stay. This place has everything you could want and need. Very spacious for 2-3 people and has all the amenities."
United States
Calvin F.
The price is AU$538
includes taxes & fees
25 Sept - 26 Sept
FALL IN MAUI!!! Perfect Island Getaway
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

Kohea Kai Hotel Maui

Kohea Kai Hotel Maui

10/10 Excellent
"Room was clean nice staff"
Grace Dawn 1-night trip
Posted 2 hours ago
Kohea Kai Hotel Maui

Find out more about Kaupakulua

Everything you need to know about Kaupakulua 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 Kaupakulua 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 Kaupakulua holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Kaupakulua holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kaupakulua. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaupakulua 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 Kaupakulua holiday rentals we have selected for you start as low as AU$422 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Kaupakulua rentals

At Expedia, we put the best Kaupakulua 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 Kaupakulua 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 Kaupakulua 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 Kaupakulua. 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 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 Hoʻomana Spa Maui 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.