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Compare 243 Vacation Homes in Kaupakulua with updated reviews, rates, and availability.

Beautiful 3-bedroom townhome in Kihei

Beautiful 3-bedroom townhome in Kihei

Mountain to Ocean Views Pole House @ Maui Adventure Villa

10.0 out of 10, Exceptional, (222)
"Staying at Pole House offers the best of Maui. With panoramic views, a wraparound lanai, very comfortable bed and exquisite architectural design, our weeklong stay was very special. We will be back."
Mountain to Ocean Views Pole House @ Maui Adventure Villa

Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach

9.4 out of 10, Exceptional, (73)
"Excellent "
Ekahi Village 44C - Beautifully appointed Ocean View Condo mins from the beach

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

9.8 out of 10, Exceptional, (198)
"great for large groups"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

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

10.0 out of 10, Exceptional, (220)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

9.6 out of 10, Exceptional, (100)
"We really enjoyed our stay."
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Very Best Deluxe Ocean View...Panoramic View....First Class!!

10.0 out of 10, Exceptional, (146)
"Everything was simply breathtaking!! What a beautiful condo and the location is second to none!!"
Very Best Deluxe Ocean View...Panoramic View....First Class!!

Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await

10.0 out of 10, Exceptional, (35)
"Everything about this place"
Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"This house is nestled inside the beginnings of the road to Hana. One of the most breathtaking places I’ve stayed in my life. Just beware, it is really hard to leave because it’s so beautiful!! The house itself is incredibly unique, there are little treasures everywhere that aren’t even pictured. "
Waterfall House - Private House Overlooking the Ocean!

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (197)
"Loved our stay. Can not wait to go back"
Kaiholo Hale

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

10.0 out of 10, Exceptional, (122)
"Nice time with our kids celebrating my husbands birthday. "
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

9.8 out of 10, Exceptional, (79)
"Great location - steps from a beach park and from a multitude of food options. Try the sushi place on the first floor of the building, it’s delicious! We had a great time during our stay. "
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

Modern 3 Bedroom Family Friendly Kihei Home Near Beach

9.8 out of 10, Exceptional, (143)
"Perfect location and great place to stay to enjoy Kihei and Wailea. Highly recommend "
Modern 3 Bedroom Family Friendly Kihei Home Near Beach

Fabulous views! Exclusive pool, spa and private 1 acre yard.

10.0 out of 10, Exceptional, (134)
"We had a great stay! The property is beautiful and close to beaches, restaurants, and groceries. It was exactly what our family of four was looking for."
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Epic Maui Camping - SUV + camping gear - Adventure on a budget

10.0 out of 10, Exceptional, (2)
"Very friendly landlord, uncomplicated early check-in, perfect vehicle and equipment, good and helpful tips for the trip"
Epic Maui Camping - SUV + camping gear - Adventure on a budget

Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

8.8 out of 10, Excellent, (49)
"All good, except the screen doors need to be fixed."
Sugar Beach Resort condo with ocean view, AC - surf, bike & golf

Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!

10.0 out of 10, Exceptional, (2)
"This place was amazing a great place to get away from everything and relax and enjoy what Maui has to offer! If you are the type who wants to get away from all of the hustle and bustle! This Place Is Heaven! William the caretaker of the property was so great. He was there to help us with anything we needed, he greeted us upon arrival and we got in rather late, showed us around and made us feel welcomed. I would definitely Love to come and stay at this Retreat again!"
Serene Eco Retreat: Ocean Views, Waterfalls, and Scenic Trails!

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

9.6 out of 10, Exceptional, (106)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
The price is AED 975
AED 3,701 total
includes taxes & fees
7 Jun - 8 Jun
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Private Oasis - 3bdrm Cottage on a Full Acre at Maui's Famous Keawakapu Beach

9.4 out of 10, Exceptional, (53)
"The property was amazing. It's a two minute walk to the beach and you have everything you need to make the trip comfortable. We would stay again anytime."
Private Oasis - 3bdrm Cottage on a Full Acre at Maui's Famous Keawakapu Beach

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (62)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AED 5,124
AED 10,105 total
includes taxes & fees
13 Jun - 14 Jun
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
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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