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Holiday Rentals in Kaupo

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Holiday Rentals in Kaupo

Our top choices for Kaupo holiday rentals

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

9.6 out of 10, Exceptional, (394)
"The property was excellent, highly recommend. "
The price is €311
includes taxes & fees
9 Sept - 10 Sept
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

9.2 out of 10, Wonderful, (105)
"An idyllic setting where we could see the bay, hear the waves, with a short walk to the beach (black rocky sands). Neighbors a bit loud, but still one of the best spots in Hāna. Easy drive to the 7 sacred pools. Good food trucks nearby. "
The price is €406
includes taxes & fees
26 Aug - 27 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep

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

10.0 out of 10, Exceptional, (67)
"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."
The price is €2,643
includes taxes & fees
10 Sept - 11 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (265)
"We had a good time, thanks for sharing your place. "
The price is €487
includes taxes & fees
1 Sept - 2 Sept
Secluded cottage on Tropical flower farm

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

10.0 out of 10, Exceptional, (80)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
The price is €474
includes taxes & fees
29 Aug - 30 Aug
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

9.6 out of 10, Exceptional, (20)
"Excellent all around property"
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

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

10.0 out of 10, Exceptional, (228)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (396)
"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!"
The price is €347
includes taxes & fees
8 Sept - 9 Sept
Fisher's Hana Bay Hale, Across from Hana Bay

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

10.0 out of 10, Exceptional, (177)
"Great place !!"
The price is €871
includes taxes & fees
26 Aug - 27 Aug
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

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

10.0 out of 10, Exceptional, (68)
"Amazing view and cozy ! One night stay but very worth it. "
The price is €612
includes taxes & fees
28 Aug - 29 Aug
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!

Beautiful Condo, Private Lanai, Near Wailea Beaches

9.6 out of 10, Exceptional, (165)
"We had a great vacation. If we come to Maui again we would choose to stay again."
Beautiful Condo, Private Lanai, Near Wailea Beaches

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"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!"
Exceptional Upcountry Villa with breathtaking views

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

9.8 out of 10, Exceptional, (250)
"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

Tropical stays where comfort meets the course

9.4 out of 10, Exceptional, (16)
"Great stay!"
Tropical stays where comfort meets the course

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."
The price is €671
includes taxes & fees
26 Aug - 27 Aug
Wailea Ekolu - CoralTree Residence Collection

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (180)
"Located a few miles beyond Hana, this is a well-equipped and very comfortable rental. "
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access (no steps), Great View!

9.6 out of 10, Exceptional, (73)
"Our second trip ! We enjoy every time ! "
The price is €367
includes taxes & fees
26 Aug - 27 Aug
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access (no steps), Great View!

AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

10.0 out of 10, Exceptional, (18)
"Awesome place for a couple nights in Hāna. "
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

10.0 out of 10, Exceptional, (194)
"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."
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

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

9.6 out of 10, Exceptional, (71)
"Best Suite & view was excellent!!"
The price is €398
includes taxes & fees
28 Aug - 29 Aug
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
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

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 €311 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.