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Holiday Rentals in Kaupo

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Holiday Rentals in Kaupo

Oceanview Condo in Hana-Let the ocean lull you to sleep
9.2 out of 10, Wonderful, (108)
"A good place to stay "
The price is €350
includes taxes & fees
25 Oct - 26 Oct
Oceanview Condo in Hana-Let the ocean lull you to sleep
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
9.6 out of 10, Exceptional, (166)
"Stayed here for 9 days with my familyOf 4. More than enough space, photos don’t do it justice. Would stay here again"
The price is €734
includes taxes & fees
18 Oct - 19 Oct
Spacious Beautifully Updated Condo, Large Lanai, Near Wailea Beaches
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, (261)
"It’s a great place to Stay for the family vacation."
Wailea Ekolu - CoralTree Residence Collection
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
10.0 out of 10, Exceptional, (70)
"Amazing Property!! Host was very friendly and gracious with time for checking in and out. Our whole family wish we could have stayed longer. Perfect spot for all of our activities"
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Exceptional Upcountry Villa with breathtaking views
10.0 out of 10, Exceptional, (45)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
Exceptional Upcountry Villa with breathtaking views
Private lush 2 Acre Mountain Home Maui w/ many amenities
10.0 out of 10, Exceptional, (230)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
Private lush 2 Acre Mountain Home Maui w/ many amenities
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
10.0 out of 10, Exceptional, (180)
"Luxury without all the people around"
The price is €947
includes taxes & fees
20 Oct - 21 Oct
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
9.8 out of 10, Exceptional, (255)
"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!"
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
9.6 out of 10, Exceptional, (402)
"We enjoyed our Stay, especially the near zu the entrance of the Volcano NP was really great."
The price is €314
includes taxes & fees
25 Oct - 26 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Secluded cottage on Tropical flower farm
9.4 out of 10, Exceptional, (272)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
The price is €490
includes taxes & fees
23 Oct - 24 Oct
Secluded cottage on Tropical flower farm
Tropical stays where comfort meets the course
9.4 out of 10, Exceptional, (18)
"Great stay!"
Tropical stays where comfort meets the course
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
9.8 out of 10, Exceptional, (158)
"An incredible and beautiful location, all the luxurious amenities, secluded and specious home away from home. The house was immaculate, comfortable, welcoming, and perfect. The pictures are spot on but arriving to the property the setting was beyond words gorgeous welcoming. An incredible 8 days!Thank you!!!!"
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
9.8 out of 10, Exceptional, (21)
"Great place, very convenient and amazing settings! "
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
10.0 out of 10, Exceptional, (87)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is €478
includes taxes & fees
26 Oct - 27 Oct
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
10.0 out of 10, Exceptional, (181)
"We loved the home and enjoy the sound of nature. Well located, near Hamoa beach"
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Fisher's Hana Bay Hale, Across from Hana Bay
9.4 out of 10, Exceptional, (406)
"Wonderful property and a great place to stay in Hana"
The price is €352
includes taxes & fees
17 Oct - 18 Oct
Fisher's Hana Bay Hale, Across from Hana Bay
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
10.0 out of 10, Exceptional, (197)
"It’s like having your own resort"
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
10.0 out of 10, Exceptional, (50)
"Our family really enjoyed this log house. Beautiful property at the best time of the year. Host was super helpful with tips on activities and attractions."
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
10.0 out of 10, Exceptional, (1)
Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
10.0 out of 10, Exceptional, (245)
"We will be back! It was perfect for us in why we wanted. Totally charmed "
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
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 Kaupo Hotel Reviews

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 €314 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. 

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?

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : This holiday home rental outside of Kaupo is located in a rural location, and has a balcony, 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 Wailua Falls 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.