Kaupo Vacation Rentals from $356: Search Short-Term Rentals

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Vacation Rentals in Kaupo

Our top choices for Kaupo vacation rentals

"The property was excellent, highly recommend. "

$306 nightly

Sep 9 - Sep 10

Total includes taxes and fees

"Perfect spot, comfy bed, clean and relaxing. An absolute dream thank you!"

$387 nightly

Aug 22 - Aug 23

Total includes taxes and fees

"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."

$2,600 nightly

Sep 10 - Sep 11

Total includes taxes and fees

"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "

$466 nightly

Aug 29 - Aug 30

Total includes taxes and fees

On the beach, sun loungers, beach towels

"Excellent all around property"

"We stayed 2 nights. Beautiful stay if you want to be off the grid. "

$477 nightly

Aug 24 - Aug 25

Total includes taxes and fees

"Lovely property and very enjoyable place to stay. Great location."

"Lovely getaway after our long on the road to Hana drive. Provided everything we needed with kitchen, 1bedroom and nice full-size bed tucked in the corner off the TV room. Loved the woody walls, plenty of ceiling fans and distant view of the bay. Check this place out folks!"

$341 nightly

Sep 8 - Sep 9

Total includes taxes and fees

"Great place !!"

$856 nightly

Aug 22 - Aug 23

Total includes taxes and fees

"Lovely home with everything we would ever need. Wonderful hosts"

"Amazing view and cozy ! One night stay but very worth it. "

$656 nightly

Aug 28 - Aug 29

Total includes taxes and fees

"We had a great time. Location is beautiful. House is comfortable, clean, and well-equipped. The view is amazing. Pool and whirlpool were a hit. Close to stores/restaurants in Makawao. Good hiking nearby. The hosts were responsive and helpful. Really can’t say enough about the views. I spent more time enjoying the views than reading my book! Didn’t even think about turning on the TV!"

"A little work to get there but the setting and activities on this side of the island are fabulous and worth several days. Eating option are limited so need to pack in some groceries. Beautiful, relaxing setting!"

"Wonderful property, very comfortable and well provisioned. Location is great!!"

$672 nightly

Aug 22 - Aug 23

Total includes taxes and fees

"We had a great vacation. If we come to Maui again we would choose to stay again."

Beach nearby, sun loungers, beach towels

"Located a few miles beyond Hana, this is a well-equipped and very comfortable rental. "

"Great stay!"

"We spent two nights at the property. We’re so glad we had extra time in Hana. We really enjoyed the covered porch with the nice breeze. The kitchen had everything we needed, and we appreciated the extra touches like having a jar of local coffee and the coffee presses. I was pleasantly surprised by the water pressure and the wonderful hot water from the solar system! And the outside shower was fantastic! If we’re ever lucky enough to come back to Hana, we would definitely stay here again. "

"Could not have been better. Cottage is a little jewel. Carrie, the host,is an amazing, kind and helpful person, Highly recommend staying at the cottage."

"Best Suite & view was excellent!!"

$391 nightly

Aug 24 - Aug 25

Total includes taxes and fees

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Top Kaupo Hotel Reviews

Hana-Maui Resort, a Destination by Hyatt Residence

10/10 Excellent

"Beautiful property with amazing views. We were complimentary upgraded to our own cottage with two adjoining rooms for our family of 4...it was perfect. Would definitely stay here again."

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

10/10 Excellent

"This is a beautiful property that easily and comfortably accommodated our family of 12. The large main house was perfect for gathering, with a spacious living room and well stocked kitchen. The grounds were gorgeous where the little ones loved running and playing, and a large pool and hot tub were great for relaxing in the evenings. The owners were wonderfully kind and accommodating, making check-in and check-out smooth and stress free. This was the perfect place for our family vacation, and we would absolutely stay here again. "

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10/10 Excellent

"This villa is beautiful and we highly recommend. Charlene and Celestine were exceptional hosts. Gave us tons of information on places to dine and things to do. The neighborhood is quiet, the property is actually a working farm. It was lovely for a quiet place to rest, but reasonably close to the airport. We all enjoyed staying there and would do it again."

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10/10 Excellent

"The property is a dream. Large house with separate entries for the walk out basement and upstairs units, perfect for two families to share. We loved the views, the fruit trees (particularly the lychees and mangoes) and my daughter was obsessed with the neighbour's goats who kept sneaking into our yard. The Eddie Tam park next door is huge and beautiful, great for sunset walks. We always stay in upcountry when we visit Maui, as we like the quiet and cooler temperatures, and central location on the island. The house had everything we needed - beach towels, sand toys, beach chairs and umbrella, small kitchen appliances, and a ton of washers and dryers so everyone could do laundry at the same time. The only negative was that the bathroom in the basement smelled awful. It was something we were able to tolerate but would reconsider staying in the basement if the problem isnt rectified. The owner was super responsive during our stay and also said she'd fix the bathroom issue. Overall we loved the place and we have wonderful memories from our visit. We look forward to returning. "

Secluded cottage on Tropical flower farm

10/10 Excellent

"We loved this house. Although it's not far off the road, it feels your in the middle of a lush tropical rainforest. The house was well furnished and the kitchen had all the supplies we needed. There were two boogie boards available for guests but there aren't many waves around Hana. One minor complaint is that it would have been helpful if there was a welcome binder with information about the house and the area."

Fisher's Hana Bay Hale, Across from Hana Bay

10/10 Excellent

"Check-in was easy, home was fun to stay and prepare our meals. At first we were concerned upon arrival as the home doesn’t have air conditioning. The home cooled down after opening windows & doors. Two fans, plus a ceiling fan kept us comfortable at night. There is a general store nearby which was helpful. Sunrise was beautiful and we enjoyed the walk to the beach from this home. Recommend staying here and thank you to our host and owner."

Exceptional Upcountry Villa with breathtaking views

10/10 Excellent

"We had the most amazing experience in Hawaii and was mostly due to where we stayed! David and Dawn were the most amazing hosts! Very responsive and helpful with restaurants, things to do and made our stay very comfortable! This place was perfect for our family of 5 and the views - stunning!! We plan to come back and know exactly where we would stay!! "

Find out more about Kaupo

Everything you need to know about Kaupo 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 Kaupo 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 Kaupo vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kaupo vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kaupo. 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 Kaupo 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 $356 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 Kaupo rentals

At Expedia, we put the best Kaupo 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 Kaupo 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 Kaupo 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 Kaupo. 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 Kaupo?

Yes, we give you a choice of vacation rentals near well known local attractions in Kaupo, or you can select a secluded option if you're looking for relaxation.

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

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : Visitors like this Kaupo vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Kaupo?

Explore the area and family-friendly sights such as Waikamoi Preserve, or get out into nature at a spot like Haleakala National Park. Bamboo Forest and Wailua Falls are a couple of places you'll find in the larger area.

What’s a vacation rental in Kaupo like?

A vacation rental is a private property you can book for a couple of days or more in Kaupo. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.

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Kaupo Vacation Rentals

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Vacation Rentals in Kaupo

Our top choices for Kaupo vacation rentals

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep

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

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Stunning views! Exclusive pool, spa and big private yard.

Stunning views! Exclusive pool, spa and big private yard.

Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Exceptional Upcountry Villa with breathtaking views

Exceptional Upcountry Villa with breathtaking views

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Wailea Ekolu - CoralTree Residence Collection

Wailea Ekolu - CoralTree Residence Collection

Beautiful Condo, Private Lanai, Near Wailea Beaches

Beautiful Condo, Private Lanai, Near Wailea Beaches

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Tropical stays where comfort meets the course

Tropical stays where comfort meets the course

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Top Kaupo Hotel Reviews

Hana-Maui Resort, a Destination by Hyatt Residence

Find out more about Kaupo

Find out more about Kaupo

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Explore a world of travel with Expedia

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