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Kaupo Vacation Rentals

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Our top choices for Kaupo vacation rentals

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, (148 reviews)
"Nice place to stay."
United States
chris
The price is CA $491
CA $937 total
includes taxes & fees
Jul 22 - Jul 23
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is CA $435
CA $769 total
includes taxes & fees
Jul 21 - Jul 22
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (519 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is CA $294
CA $553 total
includes taxes & fees
Aug 1 - Aug 2
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

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, (200 reviews)
"Comfortable, clean, well equipped cottage in the heart of Hana. Great place, highly recommend! "
United States
Michelle S.
The price is CA $246
CA $598 total
includes taxes & fees
Jul 19 - Jul 20
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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, (460 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is CA $273
CA $544 total
includes taxes & fees
Aug 1 - Aug 2
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (445 reviews)
"Great stay thanks! "
United States
Stephanie C.
Fisher's Hana Bay Hale, Across from Hana Bay

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (80 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is CA $540
CA $769 total
includes taxes & fees
Aug 5 - Aug 6
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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, (147 reviews)
"Beautiful location. Quiet and relaxing."
United States
Frank A.
The price is CA $316
CA $607 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (29 reviews)
"This place was perfect. Enjoyed 2 days of big surf and stormy weather from the lanai. A true vacation. My favorite place to stay on Maui. Hana town is da best. "
United States
Kimo B.
The price is CA $480
CA $689 total
includes taxes & fees
Jul 23 - Jul 24
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

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, (91 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is CA $675
CA $1,277 total
includes taxes & fees
Jul 25 - Jul 26
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is CA $491
CA $937 total
includes taxes & fees
Aug 6 - Aug 7
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (305 reviews)
"Beautiful secluded property. Great instuctions provided by the host. The cottage had everything we needed for our stay. "
United States
Lokahi
Secluded cottage on Tropical flower farm

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 $459
CA $653 total
includes taxes & fees
Jul 20 - Jul 21
Oceanview Hana Kai Maui #202 - Lofted Studio, Panoramic View! 2 Queen Beds!

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 $464
CA $665 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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, (84 reviews)
"Favorite stay in all of Maui"
United States
Andrew
The price is CA $429
CA $619 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

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
9.6 out of 10, Exceptional, (79 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 $440
CA $633 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (143 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is CA $1,021
CA $2,202 total
includes taxes & fees
Jul 25 - Jul 26
Hana Homestead by the Beach

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (80 reviews)
"Great beach view lovely gardens"
United States
Dianne
The price is CA $470
CA $673 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

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, (62 reviews)
"Great little place. Thanks so much for accommodating our earlier arrival. "
United States
Laura B.
The price is CA $453
CA $650 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #205 at Hana Kai Maui - 1 Bedroom Upper Floor - Amazing View!

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, (36 reviews)
"Clean, comfortable room with a wonderful view in Hana!"
United States
Amelia
The price is CA $398
CA $577 total
includes taxes & fees
Jul 19 - Jul 20
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice 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

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.