Kaupakulua Vacation Rentals

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Mar 27 - Mar 29

Vacation Rentals in Kaupakulua

Exterior
Signature Residences at Maui Banyan

Condo resort in South Kihei

4.5 star property
10.0 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
$472 nightly
The price is $556
Dec 6 - Dec 7
Total with taxes and fees
Signature Residences at Maui Banyan
Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers
Aston Maui Hill

Aparthotel in South Kihei

3.0 star property
9.0 out of 10, Wonderful, (847)
"The accommodations were comfortable, very roomy, nice view from the balcony, and staff was helpful and friendly."
United States
David
$289 nightly
The price is $341
Dec 9 - Dec 10
Total with taxes and fees
Aston Maui Hill
Garden
Yonegan Maui Getaways - Haiku

Vacation Home in Haiku

3.0 star property
8.8 out of 10, Excellent, (10)
"Loved having the hot tub to come home to!!"
United States
Pedro
$236 nightly
The price is $261
Dec 7 - Dec 8
Total with taxes and fees
Yonegan Maui Getaways - Haiku
Elite Apartment, Balcony, Ocean View | Blackout drapes, iron/ironing board, free WiFi
The Ocean View Residence

Apartment in South Kihei

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
$511 nightly
The price is $619
Dec 7 - Dec 8
Total with taxes and fees
The Ocean View Residence
View from property
The Residences at Kamaole Sands Resort

Aparthotel in South Kihei

4.5 star property
10.0 out of 10, Exceptional, (1)
"This spot was everything we needed and more. Super clean, stylish, and felt way more spacious than a typical hotel room. We had a full kitchen to cook, comfy beds for deep sleep, and the AC kept things cool after long beach days. The location couldn’t have been better—walking distance to great food, coffee, and beaches. It felt private and relaxed, but still close to the action. Honestly, it felt like home… just way better. Can’t wait to book again!"
United States
Sophie
$574 nightly
The price is $700
Dec 6 - Dec 7
Total with taxes and fees
The Residences at Kamaole Sands Resort
Property grounds
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Vacation Home in Kaʻeleku

9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
$834 nightly
The price is $971
Dec 14 - Dec 15
Total with taxes and fees
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Beach towels
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Condo in Kuau

9.4 out of 10, Exceptional, (196)
"Very quiet safe place. "
Canada
Monica
$378 nightly
The price is $440
Dec 28 - Dec 29
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Outdoor pool, a heated pool
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

Condo in North Kihei

10.0 out of 10, Exceptional, (125)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
$289 nightly
The price is $336
Dec 21 - Dec 22
Total with taxes and fees
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
Beach nearby, sun loungers, beach towels
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Condo in South Kihei

4.0 star property
9.6 out of 10, Exceptional, (48)
"Good location near beach with AC in each room, many beds were good for a larger group."
Canada
Daniel C.
$456 nightly
The price is $530
Dec 12 - Dec 13
Total with taxes and fees
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
1 bedroom, WiFi
Kuau Surf North shore Maui Locally-Owned

Apartment in Paia

9.0 out of 10, Wonderful, (36)
"Cute clean and a short couple minute walk to the beach where their was seaturtles waiting "
United States
Bobby
$339 nightly
The price is $341
Dec 7 - Dec 8
Total with taxes and fees
Kuau Surf North shore Maui Locally-Owned
On the beach
Best Oceanfront Value in Kihei - Kealia Resort!

Condo in North Kihei

9.6 out of 10, Exceptional, (109)
"The condo was exactly as described and in a great location, we loved the grassy area right in front of the beach if we didn’t feel like sitting in the sand! Tim had all the essentials for us and was quick to respond if we had any questions- we would definitely stay here again in the future! "
United States
Bailey B.
$383 nightly
The price is $446
Dec 9 - Dec 10
Total with taxes and fees
Best Oceanfront Value in Kihei - Kealia Resort!
Property grounds
Bright, Beautiful, Remodeled Island Sands 505 Condo

Condo in Wailuku

9.4 out of 10, Exceptional, (52)
"Very clean, quiet, nice people all around. Good location."
Canada
Betty T.
Bright, Beautiful, Remodeled Island Sands 505 Condo
Property grounds
Top Floor Beachfront Condo with Ocean view

Condo in North Kihei

9.8 out of 10, Exceptional, (45)
"Great stay - I would definitely recommend it"
United States
Gretchen M.
$430 nightly
The price is $500
Dec 9 - Dec 10
Total with taxes and fees
Top Floor Beachfront Condo with Ocean view
Pool
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

Condo in North Kihei

10.0 out of 10, Exceptional, (186)
"The property was amazing and was well stocked in both the kitchen as well as for all supplies. We loved our stay here and the immediate access from the patio to the beach area was amazing. We would stay here again!"
United States
Bradley L.
$591 nightly
The price is $689
Dec 9 - Dec 10
Total with taxes and fees
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121
Beach
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Condo in North Kihei

9.8 out of 10, Exceptional, (19)
"Convenient nice place to stay on Maui"
United States
Giovanni B.
$392 nightly
The price is $456
Dec 15 - Dec 16
Total with taxes and fees
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
Exterior
Kuau Surf 2.0 Maui North Shore Locally-Owned

Apartment in Paia

9.0 out of 10, Wonderful, (18)
"Cute place, had everything we needed."
United States
Jason W.
$350 nightly
The price is $352
Dec 9 - Dec 10
Total with taxes and fees
Kuau Surf 2.0 Maui North Shore Locally-Owned
Property grounds
OWNER HOST. Maui's BEST- DIRECT OCEAN FRONT Longest Sandy Beach on Maui!

Condo in North Kihei

10.0 out of 10, Exceptional, (140)
"Yes to all. Very nice! We live on Maui! Our "stay cation was awesome!"
United States
Betty
$537 nightly
The price is $625
Dec 6 - Dec 7
Total with taxes and fees
OWNER HOST. Maui's BEST- DIRECT OCEAN FRONT Longest Sandy Beach on Maui!
Pool
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking

Condo in North Kihei

9.6 out of 10, Exceptional, (165)
"The property is conveniently located with one block to the beach and marine research center. We had everything we needed for our stay. The bedroom doesn't have an A/C so we kept the door open to let living room AC provide some cool air. "
United States
Lana G.
$374 nightly
The price is $435
Dec 8 - Dec 9
Total with taxes and fees
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking
Property grounds
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Condo in Wailuku

9.6 out of 10, Exceptional, (158)
"Everything was great. Kitchen well stocked, beautiful view. "
United States
Eric S.
$403 nightly
The price is $469
Dec 21 - Dec 22
Total with taxes and fees
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Property grounds
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

Condo in North Kihei

10.0 out of 10, Exceptional, (139)
"This condo was a great find for a family trip. Easy beach access, nice (clean) pool, and very accessible to the rest of the island for a ton of activities. "
United States
Kira M.
$584 nightly
The price is $679
Dec 31 - Jan 1, 2026
Total with taxes and fees
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
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

Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

10/10 Excellent
"Room was clean, staffs are kind and the pool was big enough for my children."
Kyu H 3-night trip
Posted 1 day ago
Residence Inn by Marriott Maui Wailea

Find out more about Kaupakulua

Everything you need to know about Kaupakulua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kaupakulua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kaupakulua vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kaupakulua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $261 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kaupakulua rentals

At Expedia, we put the best Kaupakulua vacation 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 vacation.

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.

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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 Hoʻokipa Beach Park. Maui Spa Retreat and Kuau Bay Beach 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.