Holiday Homes in Upcountry Maui

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Featured Holiday Homes in Upcountry Maui and around

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (360)
"Overall very nice, reasonably priced. Would recommend adding some board games since there’s no ping pong after 7pm. Door to lanai locks but sliders to house don’t. Cute neighborhood cat! "
The price is €375
includes taxes & fees
30 Mar - 31 Mar
Fisher's Hana Bay Hale, Across from Hana Bay

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (193)
"If you are looking for a group gathering, this is the place. Location, and all other desires were right there.We were there during the last storm (Jan 2025), and did have some leaks and flooding, but that doesn't change how we felt about staying there. No one can predict the weather!I want to thank the property owner for offering such a beautiful place to vacation!!LB"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

9.8 out of 10, Exceptional, (33)
"We absolutely loved our time here and will definitely be back. Could not have been a prettier location."
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

Maui Breeze Retreat at Ho'olei! Openings March 15-21, May 12-17 & June 6-13!

10.0 out of 10, Exceptional, (128)
"Beautiful home! Great location! We had a great week on our annual family vacation, this was our first with new babies. We ran into a small issue when checking in, but all was taken care of quickly. We are planning on doing this trip every year and hope to be able to stay in same home again!"
Maui Breeze Retreat at Ho'olei! Openings March 15-21, May 12-17 & June 6-13!

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

9.8 out of 10, Exceptional, (67)
"We had a fantastic time! Everything was even better than we expected. We only wish we’d had a little more sunshine"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (195)
"A perfect area and a perfect stay! The hosts think of everything and even include some nice touches like banana bread and chocolates. The property is immaculate and the condo is extremely comfortable. We would recommend this property to anyone."
Kaiholo Hale

105-1 Puamana Spacious Townhome Near Ocean.

9.4 out of 10, Exceptional, (52)
"We checked out of this beautiful condo three days before the Maui fires. It was one of those places where we for sure will come back to. As far as I can tell, it is still standing, but the clubhouse and some surrounding buildings did burn. This is the most amazing location on the island. Will definitely be back hopefully to help rebuild, and for sure to enjoy the beauty."
105-1 Puamana Spacious Townhome Near Ocean.

Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining

8.8 out of 10, Excellent, (12)
"My family was super excited about the place and location of the Condo but when we arrived at the property the dishwasher and ice machine in the fridge did not work and when we contacted Vacasa they said it was an owner issue. The plates and mugs and silverware were not clean from the outset so we hand washed every item before using it. We then hand washed after every meal. ( There were 6 of us so a ridiculous amount of vacation time was spent at the sink!) The condo is in an amazing location but...
Oceanfront All-Suite Escape with AC & Pool | Steps to Sand | Walk to Dining

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (162)
"We stayed four nights at Hale Moana--my husband and myself, and my sister and brother-in-law. We loved it! The home was spacious and very comfortable, with bedrooms (both with king-sized beds) on either side of the house and a large living room and dining room in the center. The kitchen was also roomy and well stocked. The owner provided ample bath and beach towels, boogie boards and beach chairs. Good cross-ventilation and a house-width lanai meant we never had to turn on the A/C. The manager...
The price is €685
includes taxes & fees
30 Mar - 31 Mar
Beautiful Home in paradise!

Mountain to Ocean Views Pole House @ Maui Adventure Villa

9.8 out of 10, Exceptional, (211)
"Beautiful, high quality craftsman built home felt like living in a treehouse! We kept all the doors open our entire stay making it feel like outdoor living. The geckos were friendly, chicken & frog noises were typical of Hawaii. Easy access to all parts of the island. "
Mountain to Ocean Views Pole House @ Maui Adventure Villa

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

10.0 out of 10, Exceptional, (9)
"Loved the home, and location and it was perfect for our family. We will be back!"
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~

10.0 out of 10, Exceptional, (130)
"We were looking for a house that could accommodate 5 couples, with great outdoor space and within walking distance to the beach and shopping/restaurants. The Summit Residence did not disappoint! The house was clean and spacious with a well equipped kitchen. Lower level game room was nice and having a second full size fridge was awesome for storing drinks or overflow. We used the grill multiple times. The lanai and pool were perfect. Used daily! Plenty of extras included with the house. ...
Summit Residence at KAANAPALI VISTA~4500 sf~5B/5.5B Pool/Ocean View~

87-1 Escape to Paradise at Puamana's Hale Nalu

10.0 out of 10, Exceptional, (21)
"Loved our stay in Lahaina. The property managers were so gracious and happy to have guests back after fire and wanted us to let them know what might be needed. They were great about taking care of the few things we found. Reading some of the previous previews from before - wanted to say, there is a flashlight in closet, 4 beach chairs, 2 recliners (anti-gravity) 3 boogie boards, cooler...all of which we enjoyed. the pool was just a few houses down and very comfortable and relaxing. Really...
87-1 Escape to Paradise at Puamana's Hale Nalu

Kapalua Golf Villas by KBM Resorts

3.5 star property
10.0 out of 10, Exceptional, (3)
"Privacy was very important to me. "
The price is €1,486
includes taxes & fees
18 Mar - 19 Mar
Kapalua Golf Villas by KBM Resorts

Location, Location.... Just Steps Away from the Ocean!

9.6 out of 10, Exceptional, (134)
"This was an amazing location, so close to Lahaina & easy to get throughout the island. The condo supplies in the kitchen were great. We found this to be a great stay. If I were to be very nitpicking, the bathroom fan was very dusty & got me thinking maybe what else was dirty, however I saw nothing else. The pools need a bit of love that are in the complex, but the oceanside one was so amazing that the love that is needed to it does not even matter. I would say this is one of the best pools I...
Location, Location.... Just Steps Away from the Ocean!

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (6)
"Wonderful experience!. Accommodated 26 people with no problem at all. Beautiful house!"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (215)
"I have stayed in many rental homes and this is by far the best equipped rental home I have ever stayed in. We love to cook and usually can’t find enough pots and pans and utensils and this house had them all.We also had the privilege of their neighbors having goats and baby goats and cows which we enjoyed seeing from the deck of the house The house was also close enough to major towns And easy to find I would definitely stay here again on our next trip to Maui "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (116)
"Close to Beaches, Shopping, Awesome Restaurants, we had a blast!"
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Charming 3 BR Puamana Oceanfront in private gated community

9.6 out of 10, Exceptional, (105)
"Comfy beds, lots bathrooms, well stocked kitchen in a georgous location. Paradise! "
Charming 3 BR Puamana Oceanfront in private gated community

The Best of the Best JUST GOT BETTER with 3rd Remodel

9.8 out of 10, Exceptional, (214)
"The resort is its own oasis, from playing in the sand to swimming in the pool. The room had everything we needed, you know when you say, I wonder if they gave this or that...the answer was yes. The resort has activities each day, a Mai Tai hour. We had all the ammenities we needed. We arrived late so lots closed but we were prepared. You dont get a lot of noise from neighbors, the staff are super nice and helpful. 10 out of 10 stay! "
The Best of the Best JUST GOT BETTER with 3rd Remodel
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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Other property types in Upcountry Maui

Hawaiian Dream Temple

4.0 star property
Hawaiian Dream Temple

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3481)
"Thank you! Loved it!"
The price is €299
includes taxes & fees
14 Mar - 15 Mar
Aston Kaanapali Shores

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2719)
"Great location. Easy access to multiple pools and beach. Outstanding for family. "
The price is €849
includes taxes & fees
4 Apr - 5 Apr
OUTRIGGER Honua Kai Resort & Spa
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.