Upcountry Maui Vacation Rentals

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Browse Select Upcountry Maui Vacation Homes

STHA-2017/0002 Across from Hana Bay
Sun loungers, beach towels
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 291 reviews
"Staying in the heart of Hana in a traditional house like this was a dream :) "
STHA-2017/0002 Across from Hana Bay
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Smart TV, Netflix, DVD player, books
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
9.8 out of 10, Exceptional, 193 reviews
"We had a wonderful experience."
The price is CA $409
CA $815 total
includes taxes & fees
Jun 5 - Jun 6
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
Aerial view
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
10.0 out of 10, Exceptional, 55 reviews
"We enjoyed our stay very much. The location was very nice and the private beach area was used often. While swimming at our beach we had 3 different sea turtles swimming nearby, lots of fish to see, and a great time. Thank you for having us."
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
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Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
10.0 out of 10, Exceptional, 198 reviews
"We all (8 of us) liked the property. It had everything you need for cooking etc. Very nice appointments. We all enjoyed our stay there."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Private kitchen
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, 48 reviews
"I came with my group of around 30 and we had such a lovely time! Everyone had a comfortable place to sleep and we all enjoyed the closeness to the beach. Also, the host were very communicative and helpful throughout our stay. Highly recommend this place to anyone who wants to stay in Maui!"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Spacious Hawaiian home 50 steps from Sugar Beach!
Beach
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, 58 reviews
"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!
Privacy In Paradise - Top Rated Vacation Home in West Maui
Pool
Privacy In Paradise - Top Rated Vacation Home in West Maui
10.0 out of 10, Exceptional, 118 reviews
"This was our second time staying here. The house was clean and well stocked with everything you would need for the beach as well as a well stocked kitchen with Keurig coffee, spices and oils. The views are amazing. We spent many nights star gazing and the days in awe of the mountains and ocean views. Wouldn’t hesitate to book another stay."
Privacy In Paradise - Top Rated Vacation Home in West Maui
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
9.8 out of 10, Exceptional, 63 reviews
"Great property perfect for families. We loved it so much we actually extended our vacation and stayed an extra day. For sure will be repeat guests."
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
Sun loungers, beach towels
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
9.8 out of 10, Exceptional, 157 reviews
"The Hana house was just perfect! We especially enjoyed sleeping to the sound of the waves each night. The home was especially clean and very comfortable for our family of 7. Checkin instructions were clear and concise. Our four night stay was just as relaxing as could be. We will definitely stay at this property again if we visit Hana in the future."
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
Beach nearby
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
9.8 out of 10, Exceptional, 14 reviews
"This place was perfect for our family of 13. Kihei was the perfect place to stay at on Maui - it was close to everything, and Kihei itself was beautiful and had plenty of amazing food options. Our host was so friendly and accommodating. We didn’t need much from him because we had everything we could possibly need when we arrived. I wish we didn’t have to leave we could have stayed there forever!"
PRIVATE RESORT near Cove Park in Kihei. Sleeps up to 18 in TWO separate houses!
Beautiful Home in paradise!
Beach
Beautiful Home in paradise!
9.6 out of 10, Exceptional, 149 reviews
"Nice"
Beautiful Home in paradise!
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Beach nearby, sun loungers, beach towels
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
10.0 out of 10, Exceptional, 37 reviews
"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
Panoramic Views - Fourth Row Ho'olei - One of a Kind
Pool
Panoramic Views - Fourth Row Ho'olei - One of a Kind
10.0 out of 10, Exceptional, 18 reviews
"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
HOUSE.. ON THE BEACH MAUI
Fridge, microwave, oven, stovetop
HOUSE.. ON THE BEACH MAUI
9.8 out of 10, Exceptional, 140 reviews
"This property was just as listed and even better! Great communication with our host Brian, great location to access community and restaurants and even greater natural environment! One night we counted 36 turtles on the beach...mornings on the deck were glorious. The house is stocked with more than we expected and plenty of room for all of us. We couldn't have picked a better place."
HOUSE.. ON THE BEACH MAUI
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
Exterior
Very private. Fabulous views! Private pool, spa and yard on 1 acre!
10.0 out of 10, Exceptional, 114 reviews
"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!
Stunning Beach Front Townhouse
Property grounds
Stunning Beach Front Townhouse
10.0 out of 10, Exceptional, 79 reviews
"Property is a little dated but location and view more than make up for that drawback. You'd be hard pressed to get any closer to the water. Pool was an added bonus. Kitchen was well equiped with everything you would need to cook meals. Overall, we really enjoyed our stay here"
Stunning Beach Front Townhouse
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
10.0 out of 10, Exceptional, 48 reviews
"Beautiful house, nice property, peaceful neighborhood, very clean, amazing scenery, close to everything, awesome host!"
Maui 4 BD Heated Pool very quiet and private home in Kihei Wailea resort area
Celebrity Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
Pool
Celebrity Estate, Across the Street From Beach! Brand New! 6 Bedroom W/Pool
10.0 out of 10, Exceptional, 2 reviews
"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
Maui Breeze Retreat! Free snorkel/sail w/ new bookings 7+ nights up to 6 people!
Sun loungers
Maui Breeze Retreat! Free snorkel/sail w/ new bookings 7+ nights up to 6 people!
10.0 out of 10, Exceptional, 119 reviews
"We had a wonderful time at this Maui villa! The house is huge, very clean, and beautifully decorated. The views from our lanai were amazing, especially at sunset. Communication was great, from check in to check out. We had a small issue with the garage access code and it was fixed quickly for us. Our only suggestion is that the kitchen could be stocked with more basics like foil, olive oil, condiments, etc. There were a ton of dishes, bakeware, and tupperware which was very helpful, but having...
Maui Breeze Retreat! Free snorkel/sail w/ new bookings 7+ nights up to 6 people!
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Pool
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
9.6 out of 10, Exceptional, 84 reviews
"Clean, modern condo on a great location. Beautifully kept grounds. There’s a putting green right outside the back door and it’s only a few more steps to the pool and beach. Easy and open parking. Air conditioners worked great and we were never hot. Everyone we met at the resort was very friendly. Looking forward to returning soon. Highly recommend."
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
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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

Aston Kaanapali Shores
Hypo-allergenic bedding, in-room safe, blackout drapes
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, 3,027 reviews
"Quiet! Safe! Grocery nearby!"
The price is CA $374
CA $481 total
includes taxes & fees
Jun 12 - Jun 13
Aston Kaanapali Shores
Aston Maui Kaanapali Villas
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, 2,166 reviews
"This is more of a quiet area and has way more plants than the other hotels which made me feel more relaxed. We only called the hotel twice and maintenance came super fast and fixed everything. Loved how there is 2 pools, one big main one and one smaller with a hot tub. There’s a cafe on the beach side that is 10000/10 best spot to eat. I would def recommend, the room was super spacious as well, very private balcony "
The price is CA $324
CA $486 total
includes taxes & fees
Jun 6 - Jun 7
Aston Maui Kaanapali Villas
Kahana Beach Vacation Club
Standard Room, 1 Bedroom | Living area
Kahana Beach Vacation Club
3.0 star property
8.4 out of 10, Very good, 546 reviews
"My daughter and I had an amazing time here celebrating her master's degree. We booked a 1 BR and are so glad we did. The condo was HUGE. The bedroom was x-large, as well as the living are. Both with a large TV in each. We also had two full bathrooms (one with a tub and the other with a full size shower). The kitchen had everything you'd need to cook meals. We were pleasantly surprised with all the cooking tools and gadgets. Being recently renovated, everything was brand new. The only thing...
Kahana Beach Vacation Club
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 Vacation Homes information

Number of reviews
1,768
Accommodation
88 Vacation Homes
Lowest Price
CA $409
Highest Price
CA $409

Recent Reviews in Upcountry Maui
Expedia verified reviews

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

5/5 Excellent
"Great property for the price. Loved everything about it but what really stands out is the friendliness and customer service was top notch. Will definitely go there again "
A verified traveller stayed at OUTRIGGER Kaanapali Beach Resort
Posted 14 hours ago
OUTRIGGER Kaanapali Beach Resort