Upcountry Maui Holiday Rentals from €243: Search Short-Term Rentals

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Holiday Rentals in Upcountry Maui

"We had an excellent time staying three nights at the Aston! We ate at the restaurant and it was great. The amenities are great and the staff went above and beyond our expectations. We used the concierge for booking a luau and it was fantastic. Five stars all around! "

includes taxes & fees

8 Dec - 9 Dec

4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "

includes taxes & fees

9 Dec - 10 Dec

"Great property in perfect location adjacent to walking path & snorkeling beach. We loved our one-bedroom unit and enjoyed the resorts amenities including pools and restaurants. Well maintained, very clean, friendly staff, wish we could have extended our stay, but not easy to do at a timeshare property like you can at a hotel. That said, we wouldn't hesitate to return, next time for a longer visit. Mahalo!"

includes taxes & fees

1 Dec - 2 Dec

"The Exterior property was A little dated. But the interior rooms were Updated and very clean. The garden area with plants and adorable little cats running around, making sure there were no “pests” around was beautifully manicured. We had a wonderful time. Would visit and stay there again."

includes taxes & fees

7 Dec - 8 Dec

"It needs a bar"

"We love this place. We stay here to relax and enjoy the view. Also the staff is wonderful!"

"Amazing! Right on the beach. Staff was friendly and incredible. Had the best experience! Can’t wait to be back. "

"The beach was in your backyard. I’ve seen multiple turtles. There’s a cute delicious deli on the property. Away from the busy areas but close enough for a short drive. Just a perfect getaway "

"Can’t say enough good things about Napili Shores to stay will definitely be back"

"Great!"

Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers

"The apartment was beautifully decorated. Very clean. The grounds lovely, and a short distance to a strip of beach. The pool was closed for renovation, which was disappointing, as it looked beautiful and to be a respectable size. Monday night happy hour with all residents was a wonderful. treat. Drinks and food! We were the youngest in the crowd at 30's and 50's.The beds were comfortable. The kitchen has no oven and was not well equipped; we figured it out. Truly a nice place. This is located at...

"We had a great stay at the Napili Surf Resort. We travel with seniors and kid. The staff are helping and welcolmeing. Everybody is happy. The full kitchen gave us additional option for food. There are 2 restaurants on the beach and Napili market is around the corner. And the resort was very quiet after 8 or 9pm. There are not so many people crowed down on the beach so we enjoyed a calm and relaxed time on the beach either. We will definitely come back. "

Outdoor pool, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

"We loved our time at the Whaler however our room needed an upgrade as it looked like it was from the 80’s. Everything else perfect. Staff wonderful!!"

includes taxes & fees

29 Nov - 30 Nov

"Very Nice Soot! Cozy!"

includes taxes & fees

1 Dec - 2 Dec

"Originally we were checked into a smaller 3rd story room when we believed we were supposed to have a different ground floor. We advised them at check in, and though we would have still had a great vacation in this room, the management quickly remedied the situation and made our stay so much more pleasant. Everyone was so kind and gracious. The property and stay were perfect!"

"The pool and the location of the proximity to the rims was very good also the proximity to Beach and the view of the ocean was very nice and the proximity to shopping and dining was very good also the only thing we did not really like is the size of the restrooms and the updating of the restrooms were not very good and they should be renovated "

"It is a nice rental property in a nice location overall. It has multiple buildings and units with b ACH direct access. There are several swimming pools, many people have fun playing in swimming poor. Also it is one of best sunsets from the main swimming poor and from the central lawn field. I am really enjoyed. The unit we stayed is large one bed room equipped with a full kitchen set, if someone like cook inside. There are many high ended restaurants and a shopping mall in a short during...

Villa, 1 Bedroom, Oceanfront (Bay 36B3 Gold ,1Bath)

"Loved the property and location. Only issue is that eating establishments are somewhat limited in variety and price and most require advance reservations. I found I would drive to kanapali for more options"

includes taxes & fees

12 Dec - 13 Dec

"Beautiful time as usual…"

"Lisa at the front desk was so friendly, helpful and a delight, really enjoyed this property. Would recommend it too others."

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Other types of properties in Upcountry Maui you may be interested in

"We had an excellent time staying three nights at the Aston! We ate at the restaurant and it was great. The amenities are great and the staff went above and beyond our expectations. We used the concierge for booking a luau and it was fantastic. Five stars all around! "

includes taxes & fees

8 Dec - 9 Dec

"Everything was excellent. The people are incredibly friendly, and the ambiance is outstanding. The location is also conveniently close to shopping and dining areas in Wailea. However, the pool and resort were a bit too quiet—I would have enjoyed some lively music by the pool."

includes taxes & fees

18 Dec - 19 Dec

"Excellent Resort. Staff is very welcoming and friendly. Rooms are nice and clean. 1 minute walk to the beach. 10/10 !"

includes taxes & fees

18 Dec - 19 Dec

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, apart-hotels, 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 favorite 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 depends 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 €243 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Upcountry Maui properties

5/5 Excellent

"The rooms are clean and comfortable. Staff is helpful and friendly. The pool area is immaculate and and open from 7 am to 10 pm. We will only stay at this location for our vacations to Maui. Walking distace to several shopping areas and beaches. "

A verified traveller stayed at Maui Coast Hotel

Posted 23 hours ago

5/5 Excellent

"Some things were not working in our room, e.g. master bedroom balcony door would not open, table in the balcony was very wobbly, dryer was not operating properly. All these issues were resolved by the staff when I called them, but they seem to be basic checks that property management should have checked before giving us keys and not have me call about them. "

A verified traveller stayed at OUTRIGGER Honua Kai Resort & Spa

Posted 4 days ago

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Holiday Rentals in Upcountry Maui

Check Upcountry Maui holiday rental availability

Holiday Rentals in Upcountry Maui

Aston Kaanapali Shores

Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

Kaanapali Alii

Kaanapali Alii

Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

Sugar Beach Resort

Sugar Beach Resort

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

Maui Beach Vacation Club

Maui Beach Vacation Club

Aston Maui Hill

Aston Maui Hill

Castle Napili Surf Beach Resort

Castle Napili Surf Beach Resort

Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

Napili Sunset on the Beach

Napili Sunset on the Beach

Aston at Papakea Resort

Aston at Papakea Resort

Maui Sunset

Maui Sunset

Wailea Ekahi - CoralTree Residence Collection

Wailea Ekahi - CoralTree Residence Collection

Kapalua Villas Maui

Kapalua Villas Maui

Maui Kamaole

Maui Kamaole

The Gardens at West Maui

The Gardens at West Maui

Other types of properties in Upcountry Maui you may be interested in

Aston Kaanapali Shores

Aston Kaanapali Shores

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

Find out more about Upcountry Maui

Find out more about Upcountry Maui

Recent reviews of Upcountry Maui properties

Recent reviews of Upcountry Maui properties

Maui Coast Hotel

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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