Kaupo Holiday Rentals from €372: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Kaupo has to offer?

STHA-2017/0002 Across from Hana Bay : This holiday home rental outside of Kaupo is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

Check Kaupo holiday rental availability

Holiday Rentals in Kaupo

"We loved this property! It was more then what we were expected, so comfortable and quiet and super clean and very spacious, we will stay here again."

"My favorite part of the property was the outdoor bed on the screen-in porch, had the best night of sleep of my whole vacation sleeping outside"

"Great place. Wish we had coffee too"

includes taxes & fees

2 Feb - 3 Feb

"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the...

"From the minute we entered this residence, we were in love. From the cleanliness to the view, the property and the pool, it was all nothing short of amazing! It was the perfect home base for our families first trip to Maui and it will definitely be the place we stay in the future! "

Beach nearby, sun-loungers, beach towels

"Nice week stay- location was great. Very quiet and walking to a beach. Loved the house and grounds. Enjoyed the geekos."

"Had a wonderful time staying in this lovely cottage set in the midst of all the Hawaiian trees and flowers. Was just a visual delight. The house was clean and wonderful. Thank You"

includes taxes & fees

29 Jan - 30 Jan

"Easy access to the unit from the parking lot was very helpful for unloading luggage. Room was clean; fresh flowers a nice touch. The table, chairs, and bed on the porch made for great relaxation to the sound of the ocean. Full-size refrigerator was a plus because we travel with our own food and the WIFI worked well. Although pricey for its size, this compact unit was a perfect base for exploring the area."

includes taxes & fees

3 Feb - 4 Feb

"Nothing but peace and relaxation. Exactly what we were looking for. At first we wondered how it would be to work with the outdoor kitchen and eating space, but our first meal immediately dispelled any concern and we were thrilled with the arrangement (and the kitchen is very well-equipped). We walked to the fruit stand (much more than only fruit) about a mile away every day and Mercury has a great list of activity suggestions. We would revisit in a heartbeat."

"Our family enjoyed a mellow night at the Hana Kai Maui, with beautiful views, a full kitchen (we made dinner), soft breezes and good rests for everyone. Our teenagers were on the sofa bed and said it was super comfortable."

includes taxes & fees

15 Jan - 16 Jan

"There were 9 of us for this stay and the house was perfect for all of us! We had plenty of room to spread out after being tired from the beach all day, or the huge family room was optimal for watching a movie or hanging out. The pool was a lot of fun and everything was easy to figure out around the house. The host was very kind and gave recommendations as well as checked on us to make sure we had what we needed! Would love to come back! "

"We loved this little spot. Fabulous view that we enjoyed with the moon reflecting off the ocean, a huge lawn to play on and super close to Koki, Hamoa and Hana. We would have loved to stay longer! "

"We had a wonderful stay. The house was as advertised regarding all amenities. Very clean, well maintained and well stocked. The only surprise was no microwave. Check in and out quite seamless. One of the better properties I've rented "

includes taxes & fees

16 Jan - 17 Jan

"Only problem was getting into the house - code would not work, apparently an internet problem. Cypher Lock on upstairs door was in process of being replaced so had to use a single physical key. Otherwise, loved the house, the amenities (provided beach gear, grill, washer/driers, kitchen, etc. Master bed high for short-legged oriental. Relationship with owner exceptional."

"Enjoyed our stay at this spot in Hana. The owners do a great job at providing essentials and even had beach chairs which came in so handy! Loved the stay and a perfect way for us to rest after doing the Highway to Hana. The only thing: the GPS didn’t quite bring us here but we figured it out!"

includes taxes & fees

10 Jan - 11 Jan

"This was our second stay here - loved it enough the first time to return! It is clean, well maintained, very nicely furnished and stocked. Appliances are all top notch, accessories like coffee maker, toaster, blender - all there. Bed was comfortable, bathrooms and showers were clean and very nice. Best of all was the view and location. This unit must have the best sunsets in the complex, and the location gives easy access to the shops of Wailea (a 10 minute walk), and is close to Makena, Wailea...

"Great spot for enjoying in and around Hana. Beautiful and spacious with great scenery. We even shot some family pictures there. Quiet and peaceful - great spot to relax."

On the beach, sun-loungers, beach towels

"Beautiful view"

"This was a nice one night stay for us in Hana. While not on the ocean, you could hear it at night. Very clean."

includes taxes & fees

8 Feb - 9 Feb

"We would stay in this home again, 10/10- the only downside is we enjoyed being in the house so much we were not motivated to explore the island! The pool is lovely- a nice sized pool to enjoy as a family of four. I spent most of my time on the back deck, enjoying the view of the pool with the ocean in the distance. The landscaping is top-notCh and there are a variety of curious birds and little lizards to watch. The bedrooms are spacious and comfortable, the kitchen is well-appointed. We had a...

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Other types of properties in Kaupo you may be interested in

"This is a small, quiet resort with beautiful views of the ocean. The bungalows are very comfortable. It was a very relaxing place to stay for a couple of days while hiking and exploring Hana and the surrounding area. The staff was very attentive and friendly. Recommend waking up for an early morning swim while watching the sun rise over the ocean!"

includes taxes & fees

12 Jan - 13 Jan

"Hotel Wailea is a gem! Beautiful grounds and stunning architectural designs! Impeccable service and attention to guest needs. No better hotel in Maui!"

includes taxes & fees

21 Jan - 22 Jan

"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the...

Find out more about Kaupo

Everything you need to know about Kaupo holiday rentals

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

Kaupo holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaupo holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaupo holiday rentals we have selected for you start as low as €372 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kaupo rentals

At Expedia, we put the best Kaupo holiday 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 holiday.

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.

Recent reviews of Kaupo properties

Hana-Maui Resort, a Destination by Hyatt Residence

5/5 Excellent

"This is a small, quiet resort with beautiful views of the ocean. The bungalows are very comfortable. It was a very relaxing place to stay for a couple of days while hiking and exploring Hana and the surrounding area. The staff was very attentive and friendly. Recommend waking up for an early morning swim while watching the sun rise over the ocean!"

A verified traveller from Middle Grove stayed at Hana-Maui Resort, a Destination by Hyatt Residence

Posted 3 days ago

Great location between Hana Town and Hamoa Beach, private, family-friendly

5/5 Excellent

Fabulous location!

"We loved this little spot. Fabulous view that we enjoyed with the moon reflecting off the ocean, a huge lawn to play on and super close to Koki, Hamoa and Hana. We would have loved to stay longer! "

A verified traveller stayed at Great location between Hana Town and Hamoa Beach, private, family-friendly

Posted 3 weeks ago

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

5/5 Excellent

Amazing everything

"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the star of the show and much fun was had by all swimming and sliding and enjoying our very own little waterfall! When not at the pool, the owners had some beach gear (chairs and even boogie boards). Some incredible beaches that were 5-10 min drive from the place left us with so many great choices. Would absolutely stay here again. "

A verified traveller stayed at Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Posted 3 weeks ago

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

5/5 Excellent

"Enjoyed our stay at this spot in Hana. The owners do a great job at providing essentials and even had beach chairs which came in so handy! Loved the stay and a perfect way for us to rest after doing the Highway to Hana. The only thing: the GPS didn’t quite bring us here but we figured it out!"

A verified traveller stayed at Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Posted 3 weeks ago

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

5/5 Excellent

Maui Family Trip

"There were 9 of us for this stay and the house was perfect for all of us! We had plenty of room to spread out after being tired from the beach all day, or the huge family room was optimal for watching a movie or hanging out. The pool was a lot of fun and everything was easy to figure out around the house. The host was very kind and gave recommendations as well as checked on us to make sure we had what we needed! Would love to come back! "

A verified traveller stayed at 4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

Posted 3 weeks ago

5/5 Excellent

"This is an older place that has been kept in excellent condition. Very nice, clean, and comfortable. Everything in the place is neat and clean. The instructions from the owner, impeccable. Anything and everything you could possibly need to know is described. Good location to food and beach. "

A verified traveller from Watsonville stayed at STHA-2017/0002 Across from Hana Bay

Posted 1 month ago

Frequently asked questions

Are there holiday rentals in Kaupo?

Yes, there are holiday rentals close to the most popular sights in Kaupo, 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 Kaupo has to offer?

STHA-2017/0002 Across from Hana Bay: This holiday home rental outside of Kaupo is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most 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 Ohe'o Gulch are a couple of places you'll find in the wider area.

What’s a holiday rental in Kaupo like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaupo. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.

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Holiday Rentals in Kaupo

Plan, book, stay with confidence

Check Kaupo holiday rental availability

Holiday Rentals in Kaupo

Wailea Ekolu - CoralTree Residence Collection

Wailea Ekolu - CoralTree Residence Collection

STHA-2017/0002 Across from Hana Bay

STHA-2017/0002 Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Fabulous views! Exclusive pool, spa and private 1 acre yard.

Fabulous views! Exclusive pool, spa and private 1 acre yard.

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm

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

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

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

#708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

Beautiful Home in paradise!

Beautiful Home in paradise!

Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!

Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!

Stay in Hana #1

Stay in Hana #1

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Other types of properties in Kaupo you may be interested in

Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Find out more about Kaupo

Find out more about Kaupo

Recent reviews of Kaupo properties

Recent reviews of Kaupo properties

Hana-Maui Resort, a Destination by Hyatt Residence

Frequently asked questions