Kaupakulua Holiday Rentals

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Holiday Rentals in Kaupakulua

Suite, 2 Bedrooms | Living area
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (619)
"Nice and clean. Great value for the price "
Maui Beach Vacation Club
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (981)
"I liked this place because it was centrally located on the island, on the beach, nice view, spacious and clean."
Sugar Beach Resort
Aerial view
Maui Banyan Vacation Club
3.0 star property
8.0 out of 10, Very good, (288)
"Everything was close to us enjoyed our stay planning a second trip soon "
Maui Banyan Vacation Club
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Outdoor pool, pool loungers
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (696)
"It was a safe area, it was central to our needs. Easy Parking"
Aston Maui Hill
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (313)
"Very friendly and clean "
Maui Sunset
Exterior
Maui Kamaole
3.5 star property
8.8 out of 10, Excellent, (793)
"We enjoyed our stay very pleasant , clean and everything we needed was available thank you would definetl"
Maui Kamaole
Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (359)
"Good place"
Maui Schooner Resort
Deluxe Condo, 3 Bedrooms | Balcony
Castle Kama'ole Sands
3.0 star property
8.0 out of 10, Very good, (2143)
"This was a perfect way to lay your head for my stay. "
Castle Kama'ole Sands
Exterior
Wailea Ekahi - CoralTree Residence Collection
3.0 star property
9.2 out of 10, Wonderful, (468)
"Close to the beach and beautiful"
Wailea Ekahi - CoralTree Residence Collection
Beach nearby
Kihei Akahi
3.0 star property
8.2 out of 10, Very good, (569)
"We love this part of the beach and Kihei Akahi meets all our needs. The unit is spacious enough and has been remodeled. Everything was in good working order. This is our 4th stay at Kihei Akahi. "
Kihei Akahi
Outdoor pool
Palms at Wailea Maui
3.5 star property
8.4 out of 10, Very good, (464)
"This condo was absolutely gorgeous! The air conditioner was wonderful. I would definitely recommend this place. Amazing view from the Lani. "
Palms at Wailea Maui
2 outdoor pools, pool loungers
Hale Kamaole
3.0 star property
8.4 out of 10, Very good, (321)
"Great location, amazing room! One thing to improve on is to get another fan or AC in the living room because that area gets hot easily"
Hale Kamaole
2 outdoor pools
Wailea Grand Champions - CoralTree Residence Collection
3.0 star property
9.0 out of 10, Wonderful, (661)
"WiFi had issue and Technical support had to come to condo to repair. Master bathroom toilet had to been leaking and owner had to be contacted fir approval to be replaced during our stay and left us with 1 toilet to share for 24 hours. We had to inconvenience our invited guest with this situation. "
Wailea Grand Champions - CoralTree Residence Collection
Beach nearby, sun-loungers, beach towels
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
9.8 out of 10, Exceptional, (261)
"I needed a break from everyone and this condo is perfect! Located in the middle of everything and ever so private!"
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
Property grounds
REMODELED Maui Oceanfront Condo w/Pool, Sandy Beach & the sounds of gentle Waves
9.6 out of 10, Exceptional, (91)
"Barbs condo was absolutely perfect! Great location- we were able to walk to the harbor with shops and restaurants. Central location to easily access all parts of Maui. Condo was super clean and well equipped. Barb has everything you need to make you feel at home. Beach chairs, umbrellas, bamboo beach mats, towels, toys, a couple pairs of snorkel gear We would definitely stay here again!.."
REMODELED Maui Oceanfront Condo w/Pool, Sandy Beach & the sounds of gentle Waves
2 outdoor pools, free pool cabanas, pool umbrellas
Wailea Beach Villas
4.5 star property
9.8 out of 10, Exceptional, (154)
"Incredible! Excellent from start to finish!"
Wailea Beach Villas
Exterior
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
10.0 out of 10, Exceptional, (223)
"Lovely little place perfect for our family vacation. Very central to everything with a beach and fish pond right across the street. The owner was easy to reach if we needed anything and communication was stellar! We were surprised at all that was there when we arrived, such as stocked items in the freezer and cupboards paid forward by previous guests and playing cards and books in the drawer when you have some downtime. Absolutely all you need and more for a very good price!"
The price is NZ$668
includes taxes & fees
29 May - 30 May
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
Outdoor pool
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
9.8 out of 10, Exceptional, (138)
"Nice property."
The price is NZ$823
includes taxes & fees
29 May - 30 May
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Dining
5 STAR OCEANFRONT—FANTASTIC VIEW & AMENITIES—Newly Renovated Kitchen, Living Rm
9.6 out of 10, Exceptional, (96)
"The view was stunning, location centrally located to all activities. I would highly recommend this property"
5 STAR OCEANFRONT—FANTASTIC VIEW & AMENITIES—Newly Renovated Kitchen, Living Rm
Condo, 1 Queen Bed with Sofa bed, Balcony, Ocean View (#C-513) | Private kitchen
Kihei Akahi by VTrips
4.0 star property
7.6 out of 10, Good, (24)
"Central location for Kehie Town. Bed was hard, bathroom small. TV hard to work. Bedroom warm not air conditioned (room). Overall good. "
Kihei Akahi by VTrips
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See all available properties in Kaupakulua
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.

Other types of properties in Kaupakulua you may be interested in

Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers
Maui Coast Hotel
3.5 star property
9.2 out of 10, Wonderful, (1002)
"We went with our 2 children. The hotel was clean and close to beaches and shopping. The room was clean and we felt safe there. The view from the balcony was beautiful. The room was cool and quiet. We really enjoyed our stay there and I highly recommend it! "
The price is NZ$575
includes taxes & fees
2 Jun - 3 Jun
Maui Coast Hotel
2 bars/lounges, 2 poolside bars, swim-up bar
Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
9.0 out of 10, Wonderful, (999)
"Ocean view"
The price is NZ$1,683
includes taxes & fees
3 Jun - 4 Jun
Grand Wailea Maui, A Waldorf Astoria Resort
View from room
Fairmont Kea Lani Maui
4.5 star property
9.4 out of 10, Exceptional, (999)
"Property, room, and service top notch. KO restaurant and breakfast buffet was decent but overpriced. Wouldn’t stop us from visiting again. "
The price is NZ$1,724
includes taxes & fees
4 Jun - 5 Jun
Fairmont Kea Lani Maui
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kaupakulua holiday 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. 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 holiday just got upgraded.

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

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?

Very private. Fabulous views! Private pool, spa and yard on 1 acre! : This holiday home rental outside of Kaupakulua is located in a rural location, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Kaupakulua?

Choose from 3 Expedia holiday rentals in Kaupakulua for a memorable holiday.

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 Hookipa Beach Park. Kuau Bay Beach and H.A. Baldwin Beach State Park 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.

Recent reviews of Kaupakulua properties
Expedia verified reviews