Photo by Tim & Nat ✈

Kaupo Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Kaupo

STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 290 reviews
"This is our second time here and it is a great place to stay. Afternoon nap on the lanai is a great way to relax. The orange cat that comes around is really sweet. Close to everything in and around Hana."
STHA-2017/0002 Across from Hana Bay
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, 241 reviews
"Loved the ocean view. Although our unit was old it was well kept and offered us every amenity."
Wailea Ekolu - CoralTree Residence Collection
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, 308 reviews
"We loved this place! Very homey and cute. Very easy to walk into town with beautiful views. The property has gorgeous landscaping and is well taken care of."
The price is CA $267
CA $546 total
includes taxes & fees
Jun 13 - Jun 14
Fisher's Hana Bay Hale, Across from Hana Bay
Save an average of 15% on thousands of hotels when you're signed in
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, 225 reviews
"You will feel right at home in this very clean, cozy lush environment. If you’re looking for a change of pace tucked in a beautiful environment look no further. My 15-year-old son and I stayed here for 4 nights and felt right at home. We enjoyed cooking in the kitchen, and although they could have a few more cooking items, we were able to make all of our favorite meals from home. I would highly recommend this place for any family and friends seeking a longer stay than most in Hana."
The price is CA $404
CA $764 total
includes taxes & fees
Jun 6 - Jun 7
Secluded cottage on Tropical flower farm
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
10.0 out of 10, Exceptional, 114 reviews
"This property exceeded our expectations and was amazing. 10 out of 10. Everything was as it should be and there was no reason to contact the Owner Mark or property manager during our stay. The views from the mid deck are amazing and the perfect place to hang out. We didn't want to leave! Mark, the Owner, is excellent and answered all of our questions prior to our stay!"
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, 130 reviews
"We had a nice stay. Nice and private place in a nice quiet neighborhood. The cabin came stocked with all the amenities one would need."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
10.0 out of 10, Exceptional, 198 reviews
"We all (8 of us) liked the property. It had everything you need for cooking etc. Very nice appointments. We all enjoyed our stay there."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, 192 reviews
"This house is even better than the listing makes it look. Clean & comfortable with a huge beautiful yard. The outdoor patio is also great with comfortable furniture & everything you could possibly ask for. We would highly recommend this house to anyone looking for a clean comfortable place to stay near Hana. We were very happy with everything and will definitely book this house again."
The price is CA $410
CA $818 total
includes taxes & fees
Jun 2 - Jun 3
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
10.0 out of 10, Exceptional, 160 reviews
"So happy we found this wonderful spot so we could easily get to the Kipahulu side of the park. The owners/managers were so helpful in providing lots of information about Hana. The architecture of the house is really unique... we loved it!"
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Relaxing home away from home- honeymoon friendly
10.0 out of 10, Exceptional, 261 reviews
"The quintessential country cottage with a view that’s unmatched."
Relaxing home away from home- honeymoon friendly
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
9.8 out of 10, Exceptional, 220 reviews
"The grounds were beautiful and the bed was super comfy. It’s near the Kipahulu District of Haleakala National Park but it’s very remote."
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.6 out of 10, Exceptional, 160 reviews
"Very nice no complaints would book again"
The price is CA $404
CA $750 total
includes taxes & fees
Jun 17 - Jun 18
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
9.8 out of 10, Exceptional, 157 reviews
"The Hana house was just perfect! We especially enjoyed sleeping to the sound of the waves each night. The home was especially clean and very comfortable for our family of 7. Checkin instructions were clear and concise. Our four night stay was just as relaxing as could be. We will definitely stay at this property again if we visit Hana in the future."
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
10.0 out of 10, Exceptional, 48 reviews
"Beautiful house, nice property, peaceful neighborhood, very clean, amazing scenery, close to everything, awesome host!"
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
Beautiful Home in paradise!
9.6 out of 10, Exceptional, 149 reviews
"Nice"
Beautiful Home in paradise!
1608 The sky in Wailea's amazing 180 view
9.8 out of 10, Exceptional, 47 reviews
"Best location. The condo is very clean and have everything you need. We will definitely book again."
The price is CA $259
CA $702 total
includes taxes & fees
Jun 9 - Jun 10
1608 The sky in Wailea's amazing 180 view
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
9.6 out of 10, Exceptional, 86 reviews
"Wanted to stay a couple nights in Hāna so we wouldn’t be rushed. Nice 1 bedroom condo with a great view of the water and adjacent black and beach. Very clean. Free on-site parking. Only drawback was noisy people upstairs stomping around overhead and dragging furniture and rolling suitcases around. Fortunately people were remarkably quiet after 8 PM. We would definitely stay here again."
The price is CA $486
CA $691 total
includes taxes & fees
Jun 6 - Jun 7
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Bay Oceanfront Cottage
10.0 out of 10, Exceptional, 6 reviews
"My husband and I spent two weeks in Maui for his birthday and to get some R&R. Staying in Hana was at the top of our vacation list, and we spent quite a bit of time looking for top-notch lodging. This cottage was absolutely spectacular! The unobstructed views of the beach, the sounds of the surf, and the quiet neighborhood were beyond our expectations! We spent a lot of time on the lanai just watching the waves crash on the beach, reading our books, eating homemage meals.... it was so...
Hana Bay Oceanfront Cottage
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
9.8 out of 10, Exceptional, 63 reviews
"Great property perfect for families. We loved it so much we actually extended our vacation and stayed an extra day. For sure will be repeat guests."
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Stay in Hana #1
8.8 out of 10, Excellent, 34 reviews
"Property located in a middle of the jungle. Vey unusual experience."
The price is CA $286
CA $516 total
includes taxes & fees
Jun 11 - Jun 12
Stay in Hana #1
Don't see what you're looking for?
See all available properties in Kaupo
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.

Other types of properties in Kaupo you may be interested in

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
9.4 out of 10, Exceptional, 951 reviews
"A truly beautiful property! The staff was all super friendly and accommodating. The rooms are spacious and comfortable. They threw in dozens of “little touches” to make us feel welcomed and appreciated. Highly recommended. By far the nicest place I’ve ever stayed!"
The price is CA $1,230
CA $1,515 total
includes taxes & fees
Jun 1 - Jun 2
Hotel Wailea, Relais & Chateaux - Adults Only
Hana-Maui Resort, a Destination by Hyatt Residence
4.0 star property
9.0 out of 10, Wonderful, 891 reviews
"The property at Hana was breathtaking. I was able to relax and unwind and the views at every turn perfect. Had a great stay and will be back! "
The price is CA $832
CA $1,053 total
includes taxes & fees
Jul 1 - Jul 2
Hana-Maui Resort, a Destination by Hyatt Residence
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 290 reviews
"This is our second time here and it is a great place to stay. Afternoon nap on the lanai is a great way to relax. The orange cat that comes around is really sweet. Close to everything in and around Hana."
STHA-2017/0002 Across from Hana Bay
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.

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 $259 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?

STHA-2017/0002 Across from Hana Bay: Visitors like this Kaupo vacation home rental. It is located in a rural location and has a patio, 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. Make the most of the selection of games in this rental home to help you unwind.

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. Kipahulu Visitor Center and Hana Forest Reserve 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.

Recent reviews of Kaupo properties
Expedia verified reviews