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Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (5 reviews)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
The price is AU$1,249
includes taxes & fees
29 June - 30 June
Haiku Hale - 3 Bedroom Maui Getaway!

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (77 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
The price is AU$4,262
includes taxes & fees
29 June - 30 June
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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 AU$666
includes taxes & fees
30 June - 1 July
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (192 reviews)
"Amazing location, great garden/ pool view. Comfortable and clean room, close to beach and snorkeling. Would definitely stay there again."
United States
Patrick James
The price is AU$369
includes taxes & fees
29 July - 30 July
Napili Village Hotel

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Hana
10.0 out of 10, Exceptional, (515 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is AU$637
includes taxes & fees
1 July - 2 July
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

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, (455 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$580
includes taxes & fees
1 July - 2 July
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, (440 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is AU$583
includes taxes & fees
11 July - 12 July
Fisher's Hana Bay Hale, Across from Hana Bay

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (212 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is AU$640
includes taxes & fees
16 July - 17 July
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (425 reviews)
"The location is simply outstanding with easy access to public transit, shopping food, and it’s literally on the beach. The views from our balcony were fabulous."
United States
Mackenzie
The price is AU$1,055
includes taxes & fees
29 June - 30 June
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,825 reviews)
"Beautiful property, beach access was terrific."
United States
Alison
The price is AU$494
includes taxes & fees
14 July - 15 July
Napili Shores Maui by OUTRIGGER

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (172 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is AU$511
includes taxes & fees
4 July - 5 July
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (10 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is AU$574
includes taxes & fees
5 July - 6 July
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (16 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is AU$611
includes taxes & fees
30 June - 1 July
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,152 reviews)
"Great Stay!!"
United States
Christopher
The price is AU$455
includes taxes & fees
30 June - 1 July
Aston Kaanapali Shores

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Hana
10.0 out of 10, Exceptional, (257 reviews)
"Beautiful place."
United States
Jessica R.
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (303 reviews)
"Exceptional host, comfy beds and pillows, great location!"
United States
Brenda C.
The price is AU$587
includes taxes & fees
29 June - 30 June
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Ekahi Ocean View Escape and close to beach (21F)

Ekahi Ocean View Escape and close to beach (21F)
Wailea
9.8 out of 10, Exceptional, (71 reviews)
"Amazing location. Right near the beach. And a great complex!"
United States
Timothy J.
The price is AU$1,380
includes taxes & fees
3 July - 4 July
Ekahi Ocean View Escape and close to beach (21F)

Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (107 reviews)
"Excellent room"
United States
Rene
The price is AU$518
includes taxes & fees
3 July - 4 July
Beautiful, Renovated, Hale Kamaole 159

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 AU$803
includes taxes & fees
10 July - 11 July
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great 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, (146 reviews)
"Nice location, comfortable accommodations. We loved the view off the lanai. "
United States
Kelly J.
The price is AU$657
includes taxes & fees
3 July - 4 July
Oceanview Condo in Hana-Let the ocean lull you to sleep
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 Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Everything you need to know about Upcountry Maui holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui holiday rental for you. At Expedia, you can take your pick from private holiday 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 Upcountry Maui holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upcountry Maui holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upcountry Maui. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upcountry Maui holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upcountry Maui holiday rentals we have selected for you start as low as AU$369 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui holiday 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 Upcountry Maui 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 Upcountry Maui holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upcountry Maui. 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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