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Holiday Rentals in Kaupo

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Our top choices for Kaupo holiday rentals

1. Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Hana
9.8 out of 10, Exceptional, (153 reviews)
"Nice place to stay."
United States
chris
The price is €528
includes taxes & fees
26 Sept - 27 Sept
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (103 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is €481
includes taxes & fees
30 Sept - 1 Oct
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

3. Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (531 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
The price is €354
includes taxes & fees
26 Sept - 27 Sept
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

4. 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!
Kaʻeleku
9.8 out of 10, Exceptional, (253 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is €530
includes taxes & fees
6 Oct - 7 Oct
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

5. Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (145 reviews)
"Hosts was great. You could tell this house was a labor of love. The woodworking was beautiful. The view from the house is amazing. There was plenty of space for the seven of us."
United States
Jennifer C.
The price is €1,447
includes taxes & fees
7 Oct - 8 Oct
Hana Homestead by the Beach

6. Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (313 reviews)
"We had a great 2 night stay here! The cottage is so peaceful and secluded, it was very cool to stay in the jungle. Was well stocked with everything we needed! "
United States
Kristina B.
The price is €498
includes taxes & fees
7 Oct - 8 Oct
Secluded cottage on Tropical flower farm

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

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (151 reviews)
"Our stay was for one night and the condo was clean, well equipped, and the ocean waves lulled us to sleep. If doing the road to Hana an overnight stay here is recommended "
United States
Jaime C.
The price is €398
includes taxes & fees
6 Oct - 7 Oct
Oceanview Condo in Hana-Let the ocean lull you to sleep

8. 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
Hana Town Center
9.6 out of 10, Exceptional, (467 reviews)
"When can we go back? What an amazing place to stay in and a great house/host."
United States
Jeffrey F.
The price is €365
includes taxes & fees
25 Sept - 26 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

9. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (101 reviews)
"The home and property are beautiful! My family had a peaceful stay in the house. We enjoyed the rain while sitting on the patio."
United States
Lauren E.
The price is €759
includes taxes & fees
27 Sept - 28 Sept
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

10. Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!

Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!
Hana Town Center
8.8 out of 10, Excellent, (37 reviews)
"It was great, we regretted not staying another night."
United States
Inon
The price is €335
includes taxes & fees
5 Oct - 6 Oct
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!

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

AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.
Hana Town Center
10.0 out of 10, Exceptional, (37 reviews)
"Amazing location, very responsive host!"
United States
Matt A.
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

12. Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (30 reviews)
"Loved the view. Property was beautiful. Great place for a couple of quiet nights in Hana."
United States
Vera G.
The price is €398
includes taxes & fees
28 Sept - 29 Sept
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

13. Oceanfront #3 at Hana Kai Maui - 1 Bedroom Corner Unit 100ʻ from Water!

Oceanfront #3 at Hana Kai Maui - 1 Bedroom Corner Unit 100ʻ from Water!
Hana Town Center
9.4 out of 10, Exceptional, (28 reviews)
"This unit was clean, roomy nicely decorated and the staff was wonderful! The view of the ocean is fantastic. In fact, I'd say the black beach is just as gorgeous as Waiʻānapanapa State Park! If you can't get a reservation for that, just stay here!"
United States
John
Oceanfront #3 at Hana Kai Maui - 1 Bedroom Corner Unit 100ʻ from Water!

14. Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!

Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (63 reviews)
"Great little place. Thanks so much for accommodating our earlier arrival. "
United States
Laura B.
The price is €435
includes taxes & fees
26 Sept - 27 Sept
Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!

15. Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.4 out of 10, Exceptional, (465 reviews)
"This property was as advertised. Not having air conditioning was uncomfortable especially in an upper apartment. Some window units would help."
United States
Jane
The price is €365
includes taxes & fees
5 Oct - 6 Oct
Fisher's Hana Bay Hale, Across from Hana Bay

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

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (120 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
The price is €446
includes taxes & fees
1 Oct - 2 Oct
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

17. Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana

Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana
Hana Town Center
9.8 out of 10, Exceptional, (7 reviews)
"Awesome spot! Would definitely stay here again, incredible host. Hāna is legendary, so glad we stayed the night. "
United States
Samuel E.
The price is €386
includes taxes & fees
14 Oct - 15 Oct
Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana

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

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Hana Town Center
9.6 out of 10, Exceptional, (39 reviews)
"Beautiful location!"
United States
Caroline D.
The price is €950
includes taxes & fees
26 Sept - 27 Sept
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

19. Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (179 reviews)
"Loved everything about it. As advertised. Will do it again."
United States
Monafou M.
The price is €585
includes taxes & fees
6 Oct - 7 Oct
Beautiful Home in paradise!

20. Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!

Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!
Hana Town Center
9.4 out of 10, Exceptional, (64 reviews)
"This condo was exactly as advertised! Wonderful property! Would definitely stay here again. This side of Maui is a must see!"
United States
Lisa S.
Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic 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

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 €335 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.

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. Haleakalā Visitor Center and Haleakala Crater 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.