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Kaupo Vacation Rentals

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Our top choices for Kaupo vacation rentals

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (107 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is CA $438
CA $776 total
includes taxes & fees
Nov 2 - Nov 3
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

2. 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, (535 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is CA $297
CA $557 total
includes taxes & fees
Nov 7 - Nov 8
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

3. 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, (466 reviews)
"Place was clean and perfect for our stay."
United States
David B.
The price is CA $276
CA $615 total
includes taxes & fees
Nov 5 - Nov 6
Fisher's Hana Bay Hale, Across from Hana Bay

4. 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, (203 reviews)
"Really great property. Dedicated assigned parking."
United States
Apurv
The price is CA $331
CA $717 total
includes taxes & fees
Oct 18 - Oct 19
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

5. 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, (472 reviews)
"Super nice place and so helpful to have for a night at the end of the Road to Hana!"
United States
Tyler M.
The price is CA $276
CA $615 total
includes taxes & fees
Nov 1 - Nov 2
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

6. Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (68 reviews)
"Everything was as described and very clean"
United States
Kathy
The price is CA $396
CA $529 total
includes taxes & fees
Oct 29 - Oct 30
Stay in Hana #2

7. 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 $451
CA $644 total
includes taxes & fees
Nov 16 - Nov 17
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

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

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!
Hana Town Center
9.4 out of 10, Exceptional, (82 reviews)
"Hana Kai is very convenient place to stay. Lanai is big and great place to hang out."
United States
Ann E.
The price is CA $379
CA $554 total
includes taxes & fees
Oct 18 - Oct 19
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

9. 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, (155 reviews)
"We were so glad that we decided to stay in Hana after the long drive on the Road to Hana! It was a very comfortable studio condo with a deck overlooking the ocean. Our only complaint was that the people staying in a nearby unit were a little loud while out on their deck. We loved the sound of the waves crashing onto the black sand beach!"
United States
Wendy
The price is CA $336
CA $647 total
includes taxes & fees
Nov 8 - Nov 9
Oceanview Condo in Hana-Let the ocean lull you to sleep

10. 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 CA $422
CA $849 total
includes taxes & fees
Oct 18 - Oct 19
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

11. 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, (102 reviews)
"The property was clean, and we enjoyed our stay in this beautiful home. The host was responsive when we asked questions. The only downside I would say was no AC as it was very hot and humid, but there is fans all around the house that helped cool us down. Overall was a good experience."
United States
Nancy
The price is CA $635
CA $1,227 total
includes taxes & fees
Oct 20 - Oct 21
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

12. 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 CA $433
CA $626 total
includes taxes & fees
Oct 19 - Oct 20
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

13. 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 CA $410
CA $596 total
includes taxes & fees
Oct 18 - Oct 19
Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!

14. 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 $424
CA $616 total
includes taxes & fees
Oct 19 - Oct 20
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

15. 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 CA $417
CA $794 total
includes taxes & fees
Oct 29 - Oct 30
Secluded cottage on Tropical flower farm

16. 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, (8 reviews)
"Our favorite place to stay in Hana by far!"
United States
Michael S.
The price is CA $495
CA $662 total
includes taxes & fees
Oct 31 - Nov 1
Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana

17. Stay in Hana Upstairs

Stay in Hana Upstairs
Hana Town Center
9.6 out of 10, Exceptional, (43 reviews)
"We enjoyed the peaceful stay and hospitality of the host. "
United States
Dahn
The price is CA $317
CA $678 total
includes taxes & fees
Oct 29 - Oct 30
Stay in Hana Upstairs

18. 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 $417
CA $605 total
includes taxes & fees
Oct 31 - Nov 1
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!

19. 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
9.4 out of 10, Exceptional, (65 reviews)
"Nice location "
United States
janie h.
The price is CA $378
CA $553 total
includes taxes & fees
Oct 18 - Oct 19
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

20. Oceanfront Hana Kai Maui #2 - Romantic Studio 100' from Water! Kitchenette

Oceanfront Hana Kai Maui #2 - Romantic Studio 100' from Water! Kitchenette
Hana Town Center
9.8 out of 10, Exceptional, (31 reviews)
"Great character and amazing location"
United States
Matthew
The price is CA $511
CA $730 total
includes taxes & fees
Oct 18 - Oct 19
Oceanfront Hana Kai Maui #2 - Romantic Studio 100' from Water! Kitchenette
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.