Photo by Tim & Nat ✈

Kaupo Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Kaupo

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

9.6 out of 10, Exceptional, (400)
"The property was excellent, highly recommend. "
The price is AU$546
includes taxes & fees
3 Oct - 4 Oct
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, (106)
"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 AU$613
includes taxes & fees
2 Oct - 3 Oct
Oceanview Condo in Hana-Let the ocean lull you to sleep

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

9.8 out of 10, Exceptional, (254)
"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, Across from Hana Bay

9.4 out of 10, Exceptional, (405)
"Wonderful property and a great place to stay in Hana"
The price is AU$612
includes taxes & fees
3 Oct - 4 Oct
Fisher's Hana Bay Hale, Across from Hana Bay

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

10.0 out of 10, Exceptional, (68)
"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

Secluded cottage on Tropical flower farm

9.4 out of 10, Exceptional, (270)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
Secluded cottage on Tropical flower farm

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

10.0 out of 10, Exceptional, (178)
"Great place !!"
The price is AU$1,714
includes taxes & fees
29 Sept - 30 Sept
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

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

10.0 out of 10, Exceptional, (83)
"After eight trips to Hawaii, this is the first place where I really felt I was in paradise. "
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

10.0 out of 10, Exceptional, (228)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

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 AU$1,130
includes taxes & fees
28 Sept - 29 Sept
Wailea Ekolu - CoralTree Residence Collection

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"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

$149 Sept Special!! Beautiful Updated Condo, Large Lanai, Near Wailea Beaches

9.6 out of 10, Exceptional, (166)
"We had a great vacation. If we come to Maui again we would choose to stay again."
The price is AU$1,347
includes taxes & fees
13 Oct - 14 Oct
$149 Sept Special!! Beautiful Updated Condo, Large Lanai, Near Wailea Beaches

Tropical stays where comfort meets the course

9.4 out of 10, Exceptional, (18)
"Great stay!"
Tropical stays where comfort meets the course

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

9.6 out of 10, Exceptional, (76)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
The price is AU$780
includes taxes & fees
6 Oct - 7 Oct
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Stay in Hana #2

9.6 out of 10, Exceptional, (40)
"We stayed over night there and it was amazing just right for a one night stay"
The price is AU$538
includes taxes & fees
2 Oct - 3 Oct
Stay in Hana #2

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

9.8 out of 10, Exceptional, (230)
"Wonderful location!"
The price is AU$932
includes taxes & fees
28 Sept - 29 Sept
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Heaven on Earth in Upcountry Maui

10.0 out of 10, Exceptional, (99)
"Beautiful place with a great view onto the central island and the sea."
Heaven on Earth in Upcountry Maui

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (181)
"This property was beautiful. We were a little nervous with no air conditioning but the breeze during the day and night was just fine. Loved having a great kitchen and washer/dryer. I would love to stay here again and hopefully one day we will. Beautiful location and viewing all the flowers and plants was amazing. "
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

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!

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

10.0 out of 10, Exceptional, (69)
"Amazing view and cozy ! One night stay but very worth it. "
The price is AU$1,257
includes taxes & fees
6 Oct - 7 Oct
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 favourite 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 depend 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 AU$538 per night. Entering your travel dates in the search wizard might find you 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.