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Kaupakulua Vacation Rentals

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Our top choices for Kaupakulua vacation rentals

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (943 reviews)
"Great stay. Grounds were nice and clean. Staff was friendly. I would stay there again."
United States
Douglas Paul Zwerner or Laura
The price is CA $398
CA $473 total
includes taxes & fees
Jul 22 - Jul 23
Aston Maui Hill

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, (213 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is CA $259
CA $622 total
includes taxes & fees
Jul 31 - Aug 1
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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 CA $555
CA $1,452 total
includes taxes & fees
Aug 12 - Aug 13
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (142 reviews)
"This is the perfect getaway spot. Great direct view of the ocean and beach. "
United States
Mike H.
The price is CA $334
CA $906 total
includes taxes & fees
Jul 19 - Jul 20
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

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, (16 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is CA $293
CA $574 total
includes taxes & fees
Jul 31 - Aug 1
Eco-Friendly Condo on Road to Hāna - Walk to Beach

Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection
4.0 star property
Wailea
9.4 out of 10, Exceptional, (116 reviews)
"Most beautiful view"
United States
Vesselina
The price is CA $1,152
CA $1,739 total
includes taxes & fees
Aug 13 - Aug 14
Makena Surf - CoralTree Residence Collection

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, (519 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is CA $294
CA $553 total
includes taxes & fees
Aug 4 - Aug 5
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (21 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 $173
CA $440 total
includes taxes & fees
Aug 16 - Aug 17
Yonegan Maui Getaways - Haiku - Unit 3

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (14 reviews)
"The Condo was perfect for our stay! Two bedrooms and two bathrooms! Plenty of space and very clean and nicely furnished. The kitchen had everything we needed and more. The location was located in a great area. Our host was wonderful with tips and recommendations! We would definitely stay here again!"
United States
Sherri W.
The price is CA $423
CA $918 total
includes taxes & fees
Jul 19 - Jul 20
Paia 2 Bedroom 2 Bathroom

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands
North Kihei
9.8 out of 10, Exceptional, (72 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was an amazing stay and a great place! I will be back!"
United States
Lauree M.
The price is CA $265
CA $842 total
includes taxes & fees
Jul 31 - Aug 1
Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10

OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10
North Kihei
9.6 out of 10, Exceptional, (105 reviews)
"Room was great, loved the beach access! View from the balcony was nice too!"
United States
Linda W.
The price is CA $363
CA $1,025 total
includes taxes & fees
Jul 19 - Jul 20
OCEANFRONT RESORT- WHALES+LOW WINTER RATES- Kihei Sands Beachfront Condo-B10

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is CA $259
CA $673 total
includes taxes & fees
Aug 16 - Aug 17
Romantic Beachfront Getaway

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is CA $214
CA $486 total
includes taxes & fees
Jul 19 - Jul 20
Yonegan Maui Getaways - Haiku - Unit 4

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, (45 reviews)
"We had a wonderful stay at this condo. It was clean, spacious, and well equipped with everything we needed. The kitchen was very convenient, and the location was great. We especially appreciated how comfortable and well maintained the condo was. We would definitely stay here again."
United States
Nataliia
The price is CA $221
CA $694 total
includes taxes & fees
Jul 20 - Jul 21
Kihei Ali'i Kai Condos with Free Parking

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, (215 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 $284
CA $670 total
includes taxes & fees
Jul 23 - Jul 24
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Newly Remodeled Steps to Sugar Beach!

Newly Remodeled Steps to Sugar Beach!
North Kihei
9.6 out of 10, Exceptional, (20 reviews)
"Place was fine for a quick stay. "
United States
Melissa K.
The price is CA $568
CA $700 total
includes taxes & fees
Jul 27 - Jul 28
Newly Remodeled Steps to Sugar Beach!

Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is CA $316
CA $706 total
includes taxes & fees
Jul 31 - Aug 1
Hale Nihi - Paia, Maui

Wailea Elua- CoralTree Residence Collection

Wailea Elua- CoralTree Residence Collection
3.5 star property
Wailea
9.6 out of 10, Exceptional, (257 reviews)
"Amazing trip"
United States
tammie
The price is CA $808
CA $1,515 total
includes taxes & fees
Aug 16 - Aug 17
Wailea Elua- CoralTree Residence Collection

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (58 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is CA $233
CA $1,150 total
includes taxes & fees
Jul 31 - Aug 1
Bright, Beautiful, Remodeled Island Sands 505 Condo

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, (279 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 $159
CA $577 total
includes taxes & fees
Jul 31 - Aug 1
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?

Kaiholo Hale: Visitors like this Kaupakulua vacation home rental. It is by the ocean and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

What’s there to see and do in Kaupakulua?

While exploring the area, visit family-friendly sights like Maui Fish Pipe, 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.