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 $826 total
includes taxes & fees
Sep 2 - Sep 3
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 $753 total
includes taxes & fees
Sep 2 - Sep 3
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 $259
CA $610 total
includes taxes & fees
Sep 2 - Sep 3
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 $340
CA $749 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 $270
CA $529 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 $561 total
includes taxes & fees
Sep 10 - Sep 11
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 $277
CA $414 total
includes taxes & fees
Sep 2 - Sep 3
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 $345
CA $503 total
includes taxes & fees
Sep 2 - Sep 3
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 $822 total
includes taxes & fees
Sep 2 - Sep 3
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 $622
CA $1,203 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 $405
CA $582 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 $381
CA $507 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 $410
CA $590 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 $475
CA $676 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kaupo. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.