Upcountry Maui Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 19 - Sep 21
In two weeks
Sep 26 - Sep 28

Vacation Rentals in Upcountry Maui

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3733)
"Great area and great place to stay"
The price is P10,692
P14,297 total
includes taxes & fees
Sep 23 - Sep 24
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2455)
"Great family resort! Huge room that was perfect for our family of 5. 2 bedrooms and a huge kitchen/living room made for the perfect staycation on Island. "
The price is P8,566
P15,157 total
includes taxes & fees
Sep 14 - Sep 15
Aston Maui Kaanapali Villas
The Whaler Resort Kaanapali Beach
Exterior

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (235)
"We had a lovely stay! I would recommend this place especially for honeymooners. "
The price is P15,437
P40,060 total
includes taxes & fees
Oct 13 - Oct 14
The Whaler Resort Kaanapali Beach
Kahana Falls Maui by VRI Americas
Living area

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (924)
"Great place! The staff was very nice and the property was very cute! Loved the waterfall pool "
Kahana Falls Maui by VRI Americas
Napili Shores Maui by OUTRIGGER
On the beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1661)
"The location was great to restaurants and the beach."
The price is P15,370
P18,131 total
includes taxes & fees
Sep 27 - Sep 28
Napili Shores Maui by OUTRIGGER
Aston Maui Hill
Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (823)
"Very nice and budget friendly."
The price is P13,708
P16,170 total
includes taxes & fees
Sep 19 - Sep 20
Aston Maui Hill
OUTRIGGER Honua Kai Resort & Spa
4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2833)
"Very clean and convenient, great location and great beaches"
The price is P20,023
P53,910 total
includes taxes & fees
Sep 16 - Sep 17
OUTRIGGER Honua Kai Resort & Spa
Aston at The Whaler on Kaanapali Beach
View from room

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1487)
"Clean with a beach view nice gym and pool "
Aston at The Whaler on Kaanapali Beach
Maui Beach Vacation Club
Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (798)
"Just a great stay! "
Maui Beach Vacation Club
Aston at Papakea Resort
Surfing/boogie boarding

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very Good, (1383)
"Everything was excellent "
Aston at Papakea Resort
The Westin Ka'anapali Ocean Resort Villas
2 outdoor pools, cabanas (surcharge), pool umbrellas

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1114)
"The resort was beautiful. The hospitality in all seas was top notch. "
The price is P25,531
P30,117 total
includes taxes & fees
Sep 21 - Sep 22
The Westin Ka'anapali Ocean Resort Villas
Kapalua Villas Maui
1 bedroom, in-room safe, individually decorated, individually furnished

Kapalua Villas Maui

4.0 star property
8.8 out of 10, Excellent, (952)
"The view of the ocean was great and I was happy just to be there. It was old and a little poorly built, windows or doors were hard to open, etc. Some renovated parts were comfortable. The dryer was broken, which was inconvenient, but housekeeping provided new towels daily and offered to do laundry for free. Cooking utensils were very well stocked"
The price is P13,154
P45,803 total
includes taxes & fees
Oct 12 - Oct 13
Kapalua Villas Maui
Aston Mahana at Kaanapali
Outdoor pool

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1645)
"My 3rd time staying here at Mahana and would come back again and again :)"
Aston Mahana at Kaanapali
Maui Sunset
Terrace/patio

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (469)
"Good place to spend your vacation "
Maui Sunset
The Westin Nanea Ocean Villas, Ka'anapali
2 outdoor pools, cabanas (surcharge), pool umbrellas

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (468)
"Very nice place to stay"
The price is P27,370
P32,287 total
includes taxes & fees
Oct 3 - Oct 4
The Westin Nanea Ocean Villas, Ka'anapali
Castle Kama'ole Sands
Balcony

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very Good, (2255)
"Great location for beach with beautiful garden views and easy close parking."
Castle Kama'ole Sands
Kahana Beach Vacation Club
Living area

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very Good, (713)
"Great place to stay "
Kahana Beach Vacation Club
Marriott's Maui Ocean Club - Lahaina & Napili Towers
3 outdoor pools, cabanas (surcharge), sun loungers

Marriott's Maui Ocean Club - Lahaina & Napili Towers

4.0 star property
8.8 out of 10, Excellent, (191)
"It was a great place to spend a vacation for the whole family. "
The price is P25,531
P30,117 total
includes taxes & fees
Sep 26 - Sep 27
Marriott's Maui Ocean Club - Lahaina & Napili Towers
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is P6,437
P13,248 total
includes taxes & fees
Oct 5 - Oct 6
Yonegan Maui Getaways - Haiku
AEI at The Mahana Kaanapali Resort
Outdoor pool, pool umbrellas, sun loungers

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (276)
"Great location and facilities "
AEI at The Mahana Kaanapali Resort
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"everything clean professional upscale quiet close to shopping"
Theodore Aaron 5-night trip
Posted 3 days ago
Aston Kaanapali Shores

Find out more about Upcountry Maui

Find out more about Upcountry Maui

Search for holiday rentals in Upcountry Maui on Expedia! You can easily find your home rentals, villas, holiday apartments in Upcountry Maui using one of the methods below:

  • View our selection of featured holiday rentals in Upcountry Maui
  • Use the map to find apartments and other holiday homes in the Upcountry Maui neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upcountry Maui while they last

Look no further and take a look at our great range of rental properties in Upcountry Maui!