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Kaupakulua Vacation Rentals

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Our top choices for Kaupakulua vacation rentals

1. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (82 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is CA $1,986
CA $4,123 total
includes taxes & fees
Sep 14 - Sep 15
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

2. 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 CA $212
CA $483 total
includes taxes & fees
Sep 7 - Sep 8
Yonegan Maui Getaways - Haiku - Unit 4

3. 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 CA $170
CA $435 total
includes taxes & fees
Sep 10 - Sep 11
Yonegan Maui Getaways - Haiku - Unit 6

4. 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, (217 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 $242
CA $602 total
includes taxes & fees
Sep 15 - Sep 16
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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

Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.
Paia
9.6 out of 10, Exceptional, (58 reviews)
"This was an amazing place to stay! So close to the beach and downtown Paia - we would totally recommend this place to any of our friends! "
United States
Lizzie B.
The price is CA $244
CA $659 total
includes taxes & fees
Sep 8 - Sep 9
Maui's best Surf, wdsurf, snorkeling by secluded beach+ AC.

6. 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 CA $264
CA $539 total
includes taxes & fees
Sep 8 - Sep 9
Eco-Friendly Condo on Road to Hāna - 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 $346
CA $749 total
includes taxes & fees
Sep 8 - Sep 9
Hale Nihi - Paia, Maui

8. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (22 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 CA $170
CA $435 total
includes taxes & fees
Sep 8 - Sep 9
Yonegan Maui Getaways - Haiku - Unit 3

9. 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 $255
CA $431 total
includes taxes & fees
Oct 1 - Oct 2
Unit 22 Waena Inn - Maui Private Suite

10. 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 $274
CA $456 total
includes taxes & fees
Sep 7 - Sep 8
Unit 23 Waena Inn - Maui Private Suite

11. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (59 reviews)
"It was a beautiful place and very cozy"
United States
Stephanie T.
The price is CA $262
CA $720 total
includes taxes & fees
Sep 7 - Sep 8
Top Floor Beachfront Condo with Ocean view

12. Book Your Maui Escape Now: Stunning Oceanfront Condo.

Book Your Maui Escape Now: Stunning Oceanfront Condo.
North Kihei
9.6 out of 10, Exceptional, (101 reviews)
"Theresa was available and responsive.everything you need and well organized. can't beat the location!"
United States
Lidia R.
The price is CA $346
CA $842 total
includes taxes & fees
Sep 11 - Sep 12
Book Your Maui Escape Now: Stunning Oceanfront Condo.

13. 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, (219 reviews)
"The location of the suite was perfect, close to the pool, hot tub and grills and still offered privacy."
United States
Laurie D.
The price is CA $293
CA $679 total
includes taxes & fees
Sep 19 - Sep 20
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

14. 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, (40 reviews)
"The host responded quickly to questions. The condo was comfortable and very clean."
United States
Anonymous traveller
The price is CA $296
CA $738 total
includes taxes & fees
Sep 7 - Sep 8
Spectacular Summer Specials - Beachfront Condo With Amazing Oceanfront Views.

15. Newly Remodeled Steps to Sugar Beach!

Newly Remodeled Steps to Sugar Beach!
North Kihei
9.8 out of 10, Exceptional, (22 reviews)
"I didn’t expect this. Beautiful property with everything you need for a comfortable stay. From the comfortable beds to the beach chairs and boards I was impressed."
United States
Angela L.
The price is CA $471
CA $578 total
includes taxes & fees
Sep 7 - Sep 8
Newly Remodeled Steps to Sugar Beach!

16. Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (33 reviews)
"Property was clean and great location to do everything we wanted to do. Was very pleased for the price!!"
United States
Rachel
The price is CA $210
CA $651 total
includes taxes & fees
Sep 7 - Sep 8
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

17. 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 CA $149
CA $709 total
includes taxes & fees
Sep 18 - Sep 19
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

18. 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, (315 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 CA $146
CA $551 total
includes taxes & fees
Sep 14 - Sep 15
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

19. New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (18 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is CA $177
CA $598 total
includes taxes & fees
Sep 9 - Sep 10
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

20. 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 CA $156
CA $570 total
includes taxes & fees
Sep 24 - Sep 25
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
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, kitchenware, and a coffee maker.

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 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.