Search Holiday Homes in Upcountry Maui

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Browse Select Upcountry Maui Holiday Homes

Private kitchen | Fridge, microwave, oven, stovetop
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (47)
"First, the property: it is more amazing than the listing/pictures can possibly project. Our family visit included 7 adult couples - each of them enjoyed a private master suite of type and quality one would expect of a top-tier luxury hotel. The suites are spread across three floors, all of which are above a bottom floor with laundry, swimming pool, outdoor bar-b-q set-up, and more-than-adequate space for lounging or (as we did) having a formal meal outdoors in a beautiful tropical setting. The...
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Sun-loungers, beach towels
Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (308)
"We only stayed one night so we did not use much, but it was nice to have a washer and dryer after our long adventure to Hana, as well a hot shower was great, and a nice bed to sleep in."
Fisher's Hana Bay Hale, Across from Hana Bay
Outdoor pool
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
10.0 out of 10, Exceptional, (72)
"We decided to leave a review after our 4th annual stay at this beautiful home. We are constantly blown away by the quality, the rare location right off Napili Bay and the 5 star management. This home can host large groups of every age also! What a treat to return each year and see the property get better and better. If you want the trip of your dreams, be sure to look here first. The furniture looks brand new every time we come"
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
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Exterior
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
10.0 out of 10, Exceptional, (114)
"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!
Beach nearby
Modern 3 Bedroom Tropical Kihei Home Near Beach
9.8 out of 10, Exceptional, (133)
"Lovely home in Kihei, well appointed, modern and comfortable. Easy walking distance to beaches, restaurants and the food trucks at South Maui Gardens!"
Modern 3 Bedroom Tropical Kihei Home Near Beach
Fridge, microwave, oven, stovetop
HOUSE.. ON THE BEACH MAUI
9.8 out of 10, Exceptional, (138)
"Our stay was filled with mornings drinking coffee on the beach as our toddlers played and sunsets with our entire family watching the turtles come up to sleep. The owner was incredibly helpful when we had questions. We had a wonderful time filled with timeless memories."
HOUSE.. ON THE BEACH MAUI
Beach nearby, sun-loungers, beach towels
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, (37)
"My wife and I just enjoyed our third visit to this property, and once again it is was just perfect. This property is a gem. The hosts are great and we will keep going back. Highly recommended."
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Pool
Panoramic Views - Fourth Row Ho'olei - One of a Kind
10.0 out of 10, Exceptional, (18)
"Beautiful property, great location, stunning views, very well appointed. Would definitely book this property again."
Panoramic Views - Fourth Row Ho'olei - One of a Kind
Beach | Sun-loungers, beach towels
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (58)
"Thai is a fabulous location. Truth about how close to beach! Our only issue was there was no table to sit at inside. No table for cards or coffee. Outside wasn’t always appropriate. Major construction going on next door was an eyesore…"
Spacious Hawaiian home 50 steps from Sugar Beach!
On the beach
The Best of the Best JUST GOT BETTER with 3rd Remodel
9.8 out of 10, Exceptional, (205)
"We had a wonderful stay at this Maui property. The unit was just as depicted, and was a perfect fit for our family of 5, plus Grandma. All the necessary kitchen items were there to make everything that we desired, and were in relatively good shape. The unit also had beach chairs, umbrella, boogie boards, and a cooler to make our daily excursions to the beach that much more fun. The property had a decent pool, and the kids really enjoyed the outdoor shuffleboard and putting green that was first...
The Best of the Best JUST GOT BETTER with 3rd Remodel
Beach nearby, beach towels
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
10.0 out of 10, Exceptional, (73)
"Dan & Kelly thought of everything with their home. It is beautiful, warm and welcoming. Had great family card games every night outside. Great location to any and everything. Would stay again for sure. Thank you!"
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Sun-loungers, beach towels
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
9.8 out of 10, Exceptional, (156)
"Hamoa beach is one of our favorite places. Since the house is a short walk to the beach we were able to spend a couple of days going back and forth to take advantage of the best times of the day. The kitchen was well stocked so we were able to make most of our meals during our time in Hana. Susie was very responsive and helpful during our stay. We would definitely stay again!"
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
Pool | Outdoor pool
Celebrity Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
10.0 out of 10, Exceptional, (2)
"After looking at dozens of home for rent, we decided on this property and do not regret the decision. It’s beautifully appointed with brand new furniture, plenty of room for a large group (we had 16) and my goodness, that beach across the street, divine! There are several areas to dine, a gorgeous pool with pool and beach toys included, and what felt like a private concierge with the manager (who lives close by). Thank you for an unforgettable vacation with my family. We will cherish the...
Celebrity Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
Sun-loungers
Maui Breeze Retreat at Ho'olei...available July 13-Aug 2 & Aug.11-23. Book now!
10.0 out of 10, Exceptional, (117)
"My family of 5 stayed at Steve’s place for 9 days. Before booking I read all of the reviews about this property and thought how can every single one be so perfectly positive. Well now I know why - - the house is just fantastic. Great location, great pool, great views, great host. You will not be disappointed in any way. I can’t even think of a single negative thing about the whole experience. Once you open up the sliding doors the entire house feels like it’s outdoors! We had a slight mishap...
Maui Breeze Retreat at Ho'olei...available July 13-Aug 2 & Aug.11-23. Book now!
Pool
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
8.8 out of 10, Excellent, (36)
"The location is amazing. The kitchen is updated. Furniture needs updating. There isn't a chest of drawers or a place other than the floor for beach clothes. The closet has plenty of hangers. The place needs a deep cleaning maintenance and fresh paint on baseboards and door molding. The bedroom carpet needs replacing. There was water leakage and it was wet and smelled musty. The property managers were very helpful with all items. I believe all will or has been taken care of. We spent most of...
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf
Aerial view
Hana Bay Oceanfront Cottage
10.0 out of 10, Exceptional, (12)
"Beautiful place to stay. We lucked out and had no rain. Very quiet location with and exquisite view. Great kitchen - very well appointed. Would definitely stay again."
Hana Bay Oceanfront Cottage
Property grounds
Mountain to Ocean Views Pole House @ Maui Adventure Villa
9.8 out of 10, Exceptional, (195)
"The place was exactly what we were looking for - beautiful, open to nature, care in every detail and away from the touristy parts of the island. Reading in the hammock swing for hours looking out over the treetops to the ocean was an absolute dream, and John was incredibly gracious, communicative and helpful. We would love to come back!"
Mountain to Ocean Views Pole House @ Maui Adventure Villa
On the beach, sun-loungers, beach towels
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
9.8 out of 10, Exceptional, (178)
"We loved our stay here! Our family of 17 had plenty of room and the house is very well stocked! We enjoyed being across from a great beach and absolutely loved having our own pool. We would stay here again in a heartbeat!"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Pool | Outdoor pool, a heated pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
9.8 out of 10, Exceptional, (128)
"The house and location were perfect for our family of 10. The neighborhood was quiet and a very short drive or 10 min walk to the beach. There was ample public parking next to the beach which was excellent for snorkelling. The pool was ideal for our 4 grandchildren and the house was beautiful and exactly as shown in the VRBO web site. Daniel was an excellent host and very responsive. We shall definitely return there"
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Outdoor pool, a heated pool
Koa Resort #5G 3BR/2BA, Large townhome, Pool, AC, WIFI, Sleeps 8
9.2 out of 10, Wonderful, (34)
"We were in Maui for a hiking trip and the property exactly meet our needs. 2nd floor 3 BR condo is one block from beach, across from pool and convenient to main road thru Kihei. Nice outdoor covered patio. Condo is fully equipped and welcome basket of goodies/coffee and bag of ice in frig were appreciated. Beach towels and equipment provided. Washer/dryers are large. Rooms have individual AC controls. Be aware upstairs loft king bedroom has a steep stairs and no door and do not leave any food or...
Koa Resort #5G 3BR/2BA, Large townhome, Pool, AC, WIFI, Sleeps 8
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See all available properties in Upcountry Maui
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 property types in Upcountry Maui

Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is £270
includes taxes & fees
27 May - 28 May
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2145)
"Beautiful grounds. Close o the pool and beach.! Castaway s great bar and restaurant. "
The price is £297
includes taxes & fees
21 May - 22 May
Aston Maui Kaanapali Villas
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2531)
"I loved everything about this resort. "
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.

Upcountry Maui Holiday Homes information

Number of reviews
1,728
Accommodation
88 Holiday Homes
Lowest Price
Highest Price

Upcountry Maui Hotel Reviews
Expedia verified reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

5/5 Excellent
"I usually visit Oahu twice a year and decided to give Maui a try. I thought nothing could top Oahu but I was wrong. I absolutely loved everything about my trip and I think a huge reason was this hotel. The staff were incredibly friendly and even remembered my name. Helene at front desk was especially great. Room was clean and newly renovated. The beach was so beautiful, gardens and hammocks offered were so nicely kept, also great restaurant and store on site. You definitely get your moneys worth booking this resort. What I also really loved about this resort was the free cultural activities offered. I was able to make my own lei and it was such a great experience. Overall this hotel is so amazing and I cant wait to visit again."
A verified traveller stayed at OUTRIGGER Kaanapali Beach Resort
Posted 1 day ago
OUTRIGGER Kaanapali Beach Resort