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Kaupakulua Vacation Rentals

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Our top choices for Kaupakulua vacation rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (41 reviews)
"Rooms were very comfortable and clean. Super easy check in and out. Great location, not touristy at all, which is what I like for a vacation! Great staff made everything super easygoing. Will definitely be back!"
United States
Jennifer
The price is CA $177
CA $420 total
includes taxes & fees
Nov 2 - Nov 3
Yonegan Maui Getaways - Haiku

2. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.2 out of 10, Wonderful, (24 reviews)
"Clean and comfortable. Enjoyed having the balconies. On the road to Hana. In a quiet neighborhood. Would definitely stay again."
United States
Gennessa R.
The price is CA $172
CA $439 total
includes taxes & fees
Nov 2 - Nov 3
Yonegan Maui Getaways - Haiku - Unit 3

3. A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (224 reviews)
"Great location for our last night. Walk to the beach and close enough to the airport for an early flight."
United States
jeff s.
The price is CA $259
CA $627 total
includes taxes & fees
Oct 31 - Nov 1
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

4. Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (99 reviews)
"Close walk to a beach. Owner took care of maintenance problem quickly."
United States
David
The price is CA $254
CA $621 total
includes taxes & fees
Oct 31 - Nov 1
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

5. Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.

Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.
Paia
9.6 out of 10, Exceptional, (61 reviews)
"Perfect location and so clean and cute inside. Hosts are wonderful, kind, and professional. Will definitely refer others and stay again!"
United States
Jessica V.
The price is CA $217
CA $627 total
includes taxes & fees
Oct 31 - Nov 1
Maui's best Surf, wdsurf, snorkeling by secluded beach+ bdAC.

6. Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach

Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach
Paia
9.8 out of 10, Exceptional, (22 reviews)
"Chloe was very helpful! Her place was very convenient for an early trip to go to Hana. The place was clean and furnished and had everything we needed. Clear instructions smooth check in&out. Chloe was also fast with responses when I had questions. Would recommend to stay here!"
United States
Janette
The price is CA $309
CA $610 total
includes taxes & fees
Oct 31 - Nov 1
Locally-Owned Eco-Friendly Condo on Road to Hana - Walk to Beach

7. 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 CA $278
CA $663 total
includes taxes & fees
Oct 31 - Nov 1
Hale Nihi - Paia, Maui

8. 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)
"The property was very clean and well-appointed. It was a great location that allowed us to walk in to Mama's Fish House. The host was extremely helpful and proactive and checked to make sure we had everything we needed. If you are looking for a place to stay in Paia, this is it."
United States
Martin S.
The price is CA $176
CA $591 total
includes taxes & fees
Nov 12 - Nov 13
Condo w/ Lanai at Beginning of Road to Hana!

9. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (43 reviews)
"Overall, our experience was great! Everything from check-in to check-out went smoothly, and the room was reasonably clean. The furniture and bedding could definitely use some updating, and the pull-out couch wasn’t the most comfortable. However, if you don’t mind slightly outdated decor, this is a great place to stay, especially if you’re visiting Maui for a short trip or plan to spend most of your time exploring the island rather than staying in your room. One of the biggest perks was the...
United States
Jennifer Mai
The price is CA $172
CA $439 total
includes taxes & fees
Nov 2 - Nov 3
Yonegan Maui Getaways - Haiku - Unit 6

10. 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, (537 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is CA $294
CA $552 total
includes taxes & fees
Nov 11 - Nov 12
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

11. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (1,000 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is CA $353
CA $419 total
includes taxes & fees
Nov 29 - Nov 30
Aston Maui Hill

12. Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (227 reviews)
"Has everything you need and you cannot beat the location. Everything works, slept great, would definitely book again"
United States
Michelle S.
The price is CA $273
CA $656 total
includes taxes & fees
Oct 30 - Oct 31
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

13. Sugar Beach PH31 Front Row Amazing Oceanviews in Highly Upgraded Unit

Sugar Beach PH31 Front Row Amazing Oceanviews in Highly Upgraded Unit
North Kihei
9.6 out of 10, Exceptional, (97 reviews)
"Amazing views from the kitchen and balcony. Incredible grill area located near the beach and pool."
United States
Tennessee_ E.
The price is CA $378
CA $907 total
includes taxes & fees
Nov 20 - Nov 21
Sugar Beach PH31 Front Row Amazing Oceanviews in Highly Upgraded Unit

14. Unit 22 Waena Inn - Maui Private Suite

Unit 22 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (38 reviews)
"The studio is super cute and in a convenient location, it was very clean and the check in process was really easy!"
United States
Claire R.
The price is CA $259
CA $439 total
includes taxes & fees
Nov 1 - Nov 2
Unit 22 Waena Inn - Maui Private Suite

15. 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 CA $255
CA $733 total
includes taxes & fees
Nov 6 - Nov 7
Kihei Ali'i Kai Condos with Free Parking

16. Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (12 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is CA $277
CA $461 total
includes taxes & fees
Oct 31 - Nov 1
Unit 23 Waena Inn - Maui Private Suite

17. 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 CA $67
CA $728 total
includes taxes & fees
Oct 30 - Oct 31
Signature Residences at Maui Banyan

18. Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
North Kihei
10.0 out of 10, Exceptional, (144 reviews)
"We really enjoy staying here at Sugar Beach!! This condo is always perfect in every way! We have stayed here multiple times and it is always a great experience. Would highly recommend this condo!!"
United States
Lela N.
The price is CA $419
CA $933 total
includes taxes & fees
Nov 19 - Nov 20
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

19. Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.

Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.
North Kihei
9.6 out of 10, Exceptional, (42 reviews)
"The host responded quickly to questions. The condo was comfortable and very clean."
United States
Anonymous traveller
The price is CA $351
CA $817 total
includes taxes & fees
Nov 6 - Nov 7
Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.

20. ~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~

~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~
North Kihei
9.8 out of 10, Exceptional, (140 reviews)
"Great location and facilities. Very convenient to all the great places on Maui."
United States
Tom
The price is CA $350
CA $833 total
includes taxes & fees
Oct 31 - Nov 1
~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Kaupakulua?

Yes, there are vacation rentals near top sights in Kaupakulua, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Kaupakulua has to offer?

Yonegan Maui Getaways - Haiku : Visitors like this Kaupakulua vacation home rental. It is located near the beach and has a hot tub, a barbecue grill, 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 larger area.

What’s a vacation rental in Kaupakulua like?

Vacation rentals are privately owned properties you can book for a long or short time in Kaupakulua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.