Kaupo Vacation Rentals from $364: Search Short-Term Rentals

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Our top choices for Kaupo vacation rentals

A stone pathway leading through a lush garden with various plants and a moss-covered stone structure.

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

Hāna

Mark S.

$460 nightly

Nov 14 - Nov 15

Total with taxes and fees

A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

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

Hana

Sonja W.

$335 nightly

Nov 11 - Nov 12

Total with taxes and fees

A lush green lawn with a gazebo, a large rock, and a view of a forested hill under a partly cloudy sky.

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

Kaʻeleku

Nancy

$672 nightly

Nov 7 - Nov 8

Total with taxes and fees

A hotel with a pool, a lawn, and a view of the ocean.

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

Hana Town Center

Timothy

$331 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Hana Town Center

Heather B.

$393 nightly

Nov 21 - Nov 22

Total with taxes and fees

A living room with a black leather sofa, two wicker chairs, a small round table with a vase of flowers, a mirror on the wall, and a ceiling fan.

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

Hana Town Center

Jennifer

$369 nightly

Nov 10 - Nov 11

Total with taxes and fees

A wooden deck with a staircase leading to a covered area, surrounded by lush greenery.

7. Stay in Hana #2

Hana Town Center

Celeste D.

$303 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Hana Town Center

Tanya L.

$356 nightly

Nov 11 - Nov 12

Total with taxes and fees

A beach with red sand, waves, and a rocky outcrop in the distance.

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

Hana Town Center

Val S.

$369 nightly

Nov 13 - Nov 14

Total with taxes and fees

A landscaped garden with a pond, palm trees, and a view of the ocean.

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

Hana Town Center

Jenilene

$311 nightly

Nov 21 - Nov 22

Total with taxes and fees

A multi-story building with balconies, surrounded by lush greenery and a beach.

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

Hana Town Center

Wendy

$369 nightly

Nov 8 - Nov 9

Total with taxes and fees

A house with a lawn and tropical plants.

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

Kaʻeleku

Mary B.

$505 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered outdoor area with a wooden deck, a table and chairs, and a sign reading "Tradewenda Cottage."

13. Secluded cottage on Tropical flower farm

Kaʻeleku

nancy

$474 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Hana Town Center

Vera G.

$359 nightly

Nov 11 - Nov 12

Total with taxes and fees

A rural landscape with a small house, palm trees, and a stop sign.

15. Hana Homestead by the Beach

Hana Town Center

MARK V.

$1,489 nightly

Nov 8 - Nov 9

Total with taxes and fees

A house surrounded by dense tropical vegetation, with a visible porch and a small garden area.

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

Hana Town Center

Michael S.

$363 nightly

Nov 7 - Nov 8

Total with taxes and fees

A wooden staircase leading to a covered outdoor area with a seating arrangement.

17. Stay in Hana #1

Hana Town Center

Amber T.

$204 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Hana Town Center

janie h.

$323 nightly

Nov 11 - Nov 12

Total with taxes and fees

A kitchen with a large island, wooden chairs, and a view of the ocean.

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

Hana Town Center

Caroline D.

$908 nightly

Nov 12 - Nov 13

Total with taxes and fees

A balcony with a round wooden table and chairs, a view of the ocean, and a kitchen area with a coffee maker.

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

Hana Town Center

Ann E.

$331 nightly

Nov 21 - Nov 22

Total with taxes and fees

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Top Kaupo Hotel Reviews

Secluded cottage on Tropical flower farm

10/10 Excellent

"The cottage was beautiful just as described. Quiet and relaxing. The host was great and even checked on us because we checked in during a storm. Check in process was so easy. I would definitely recommend."

Hana Garden Room 1 & 2 night stays, its Perfect! Lic.# BBHA20130004

10/10 Excellent

"Charming, simple, comfortable room. Perfect for our overnight in Hana, but I could easily have stayed for days and days! The host welcomed us in person when we arrived and got us all settled. There is a large en suite bathroom, and a mini fridge and small kitchen. There are 4 acres of beautiful gardens that we took a glimpse of before we left at 6:15 this morning. It’s really a very nice getaway room and I highly recommend it. Plus, there is a place just up the road called Garden Gourmet that serves wonderfully fresh Thai food. And another place just down the road with great food and music and pizza on the weekends. I highly recommend this place to anyone traveling to Hana for a quick overnight, or if you are staying even longer!"

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools

10/10 Excellent

"We had a wonderful stay at this property outside of Hāna. The location was convenient for hiking in the eastern section of Haleakalā National Park. Our room was perfect for our short two night stay, and our host went out of her way to ensure our comfort. This property has a large yard with views of the ocean in two directions. We enjoyed relaxing in the yard after our day hikes in the national park and visiting local attractions in Hāna."

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

10/10 Excellent

"Beautiful cabin home right before Hana airport. Easy to get to & to get around the east side of Maui. We are from Maui originally & it was a treat to spend the night in Hana for my son’s 24th birthday. The cabin had plenty space & extra bedding if needed. We had some people not be able to come so there was 5 of us & we had lots of space. The hosts communicated well & even accommodated a date change for us, which was very kind & appreciated. The home is cute & has fans & lots of windows, but no AC, which was okay bc we were out most of the day when it was warmer. We love Hana & can’t wait to go back Maui No Ka Oi!"

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

10/10 Excellent

"The inside is lovely, but my favorite spot was the lanai. I loved relaxing on the daybed, watching the sunrise and the waves roll in and out. It’s a beautiful, peaceful place for a getaway, with a beach nearby to enjoy! There is no AC, but with the windows open, you can enjoy the ocean breeze and let the sound of the waves lull you to sleep. A wonderful spot to unwind, relax, and enjoy the beauty of the ocean. Absolutely loved our stay here!"

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Kaupo in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $364 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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.

Kaupo Vacation Rentals

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Check prices for these dates

Our top choices for Kaupo vacation rentals

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

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

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

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

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

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

7. Stay in Hana #2

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

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

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

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

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

13. Secluded cottage on Tropical flower farm

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

15. Hana Homestead by the Beach

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

17. Stay in Hana #1

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

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

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

Find vacation rentals that suit your style

Top Kaupo Hotel Reviews

Secluded cottage on Tropical flower farm

Find out more about Kaupo

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