A two-lane road with a white dividing line, surrounded by vegetation and hills in the distance.

Kaupo Vacation Rentals

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Our top choices for Kaupo vacation 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, (151 reviews)
"Nice place to stay."
United States
chris
The price is CA $416
CA $830 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $430
CA $744 total
includes taxes & fees
Sep 30 - Oct 1
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (201 reviews)
"Comfortable, clean, well equipped cottage in the heart of Hana. Great place, highly recommend! "
United States
Michelle S.
The price is CA $310
CA $681 total
includes taxes & fees
Sep 9 - Sep 10
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

4. 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, (525 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 CA $291
CA $545 total
includes taxes & fees
Sep 5 - Sep 6
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

5. Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (161 reviews)
"This was the perfect home base for a 3-night stay in Hana! The property is exceptionally clean, comfortable, quiet, and scenic. The property manager was also incredibly responsive to all of our questions both before and during our stay. We would absolutely stay here again!"
United States
Kelly Z.
The price is CA $341
CA $751 total
includes taxes & fees
Sep 3 - Sep 4
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

6. 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, (463 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is CA $271
CA $531 total
includes taxes & fees
Sep 14 - Sep 15
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (150 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 CA $312
CA $597 total
includes taxes & fees
Sep 27 - Sep 28
Oceanview Condo in Hana-Let the ocean lull you to sleep

8. 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, (458 reviews)
"We loved staying here, and it was great for a family of 4. Kitchen very well stocked and lots of room, ping pong table a plus. Great to be able to split up Road to Hana drive."
United States
Jason C.
The price is CA $270
CA $557 total
includes taxes & fees
Oct 2 - Oct 3
Fisher's Hana Bay Hale, Across from Hana Bay

9. 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 CA $389
CA $563 total
includes taxes & fees
Sep 11 - Sep 12
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!

10. 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 CA $438
CA $629 total
includes taxes & fees
Sep 8 - Sep 9
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

11. Oceanview Hana Kai Maui #202 - Lofted Studio, Panoramic View! 2 Queen Beds!

Oceanview Hana Kai Maui #202 - Lofted Studio, Panoramic View! 2 Queen Beds!
Hana Town Center
9.6 out of 10, Exceptional, (62 reviews)
"Best place to stay in Hana!!"
Australia
Roger S.
The price is CA $496
CA $703 total
includes taxes & fees
Sep 4 - Sep 5
Oceanview Hana Kai Maui #202 - Lofted Studio, Panoramic View! 2 Queen Beds!

12. 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, (250 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is CA $412
CA $826 total
includes taxes & fees
Sep 7 - Sep 8
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

13. 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, (100 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is CA $624
CA $1,206 total
includes taxes & fees
Sep 14 - Sep 15
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

14. 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, (119 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
The price is CA $496
CA $704 total
includes taxes & fees
Sep 13 - Sep 14
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

15. Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
Hana Town Center
9.6 out of 10, Exceptional, (64 reviews)
"Nice location "
United States
janie h.
The price is CA $406
CA $584 total
includes taxes & fees
Sep 11 - Sep 12
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

16. Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (310 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 CA $409
CA $775 total
includes taxes & fees
Sep 6 - Sep 7
Secluded cottage on Tropical flower farm

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 CA $382
CA $509 total
includes taxes & fees
Sep 3 - Sep 4
Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana

18. Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Hana Town Center
9.8 out of 10, Exceptional, (85 reviews)
"Incredible property, even better than the pictures advertised. There was no AC but you are right on the ocean and the sea breeze kept us cool and comfortable the entire time with the huge windows. Would definitely come back here again!"
Canada
Celine
The price is CA $411
CA $592 total
includes taxes & fees
Sep 11 - Sep 12
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

19. Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (82 reviews)
"Great beach view lovely gardens"
United States
Dianne
The price is CA $477
CA $678 total
includes taxes & fees
Sep 11 - Sep 12
Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!

20. 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 CA $1,009
CA $2,176 total
includes taxes & fees
Sep 7 - Sep 8
Hana Homestead by the Beach
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 vacation rentals

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

Kaupo vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaupo vacation rentals we have selected for you start as low as CA $529 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 vacation 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 vacation.

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 vacation rentals in Kaupo?

Yes, we give you a choice of vacation rentals near well known local attractions in Kaupo, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental that Kaupo has to offer?

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 : Visitors like this Kaupo vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill 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 larger area.

What’s a vacation rental in Kaupo like?

A vacation rental is a private property you can book for a couple of days or more in Kaupo. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a small group gathering.