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Compare 163 Vacation Homes in Kihei with updated reviews, rates, and availability.

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

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!

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

10.0 out of 10, Exceptional, (116)
"Finding this property that accommodated multiple family members was a gem. The dual-level bedroom layout and the additional cottage for young couples offered both privacy and togetherness—a perfect combination for family gatherings. A well-stocked kitchen and large gathering space is indeed a boon, making group meals and celebrations seamless. Staying within walking distance to local amenities and enjoying breathtaking sunsets each evening was delightful. Witnessing over 13 sea turtles coming...
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

9.8 out of 10, Exceptional, (74)
"Great property with perfect location, very relaxing. It was a short driving distance to beaches, restaurants, shops- less than five minutes. Pool is not heated but warms up in the afternoon (during winter). "
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

10.0 out of 10, Exceptional, (91)
"The home was beautiful and we loved it, the only negative was very slow internet, the television keep freezing … it’s football season "
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Family-Eco Friendly House🌺Walk to beach,dining,park,shops,hot tub,AC

10.0 out of 10, Exceptional, (179)
"We had a great time staying at the house! It had more ammenities than any other vacation property we have stayed at and all the pictures and video provided of the property are exactly how it looks. The patio area was very nice and there was lots of room for our family of six. Also a very nice feature was a guide compiled by the owners of stores, restaurants, beaches, walks, and other things to do in the area which we found to be quite helpful. Jenni was very helpful. All in all we had wonderful...
Family-Eco Friendly House🌺Walk to beach,dining,park,shops,hot tub,AC

Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.

9.2 out of 10, Wonderful, (51)
"Spacious beachfront condo with every amenity that you could ever possibly need on vacation. Truly the most perfect location and Natalie is a gracious, helpful host - everything about this booking was easy and we had a wonderful time!"
Kihei Akahi A108: Kamaole Beach II Ocean View Town House directly across street.

LUXURIOUSLY*OCEANFRONT Beach House with Sweeping 180°Views

10.0 out of 10, Exceptional, (22)
"Is it a little more than what you normally have spent? Probably. But, is it really worth it? 100X yes! This place was everything we ever wanted for our oh so few family vacation. With our kids spread all over the country, it was our one chance to bribe everyone to join us at this beautiful home. The home was very spread out with master on one side (a small adjacent room we did not use). Kids stayed in the two bedrooms on the other end of the house. Large living room. Kitchen was a bit narrow,...
LUXURIOUSLY*OCEANFRONT Beach House with Sweeping 180°Views

Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

10.0 out of 10, Exceptional, (25)
"We absolutely loved our stay at Ho’olei. Eric made sure we had everything we needed. The team takes great pride in keeping the home and grounds clean. The outdoor patio with panoramic view of the ocean and proximity to the Grand Wailea resort and beach were a highlight of our stay. The home is perfect for large family gatherings and has a fully stocked kitchen. We can’t wait to plan our next adventure back to Wailea. "
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

10.0 out of 10, Exceptional, (82)
"This was such a nice relaxing vacation. We travel with a group of 3 other couples. The beaches and town are only about a 2-minute drive down the hill. Very convenient location in Kehei. Some of us that wanted to go to town could do that and some of us that wanted to relax stayed by the pool. There was a gazebo that allows us to grill, play music or put on the TV outside. We had coffee by the pool every morning and ate out under the gazebo most nights in the back yard. The host lived close by and...
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

2 Private Homes for 1! Pool & Waterslide - Cove Hale

10.0 out of 10, Exceptional, (24)
"Wonderful property, had everything we needed for 14 people for 10 days. Houses were very well supplied and comfortable. Pool, slide, hot tub, outdoor space were great. When we were at the property we were in those spaces. Location makes it possible to walk to the beach, shopping, restaurants. Nice not to have to take the car everywhere. We loved our stay at The Cove Hale!!"
2 Private Homes for 1! Pool & Waterslide - Cove Hale

OCEAN BLISS Oceanfront Private Home

9.8 out of 10, Exceptional, (99)
"We spent a blissful week in this beautiful home and the views cannot be beat! We saw whales practically every time we looked out at the ocean and the magical sunset views make this property a must stay. The beach is just steps away while also having the luxury of your own private plunge pool. The house is fully stocked and Janna was a fabulous host. We can’t wait to come back! :)"
OCEAN BLISS Oceanfront Private Home

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

9.6 out of 10, Exceptional, (93)
"Had a wonderful 7 days in Kihei - this place was great. Loved that you could walk the beautiful beach, the grounds were very well maintained, the pool was delightful and my husband was able to walk to the city park and play pickleball every morning. "
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

9.8 out of 10, Exceptional, (150)
"The experience couldn’t have been better! The house is lovely and was just what our family was looking for in being a home away from home in paradise. The house was full of useful amenities - kitchen is fully stocked; the laundry is great; and there is everything you need for the beach!The location is very close to town but far enough away to feel completely relaxed.Our family would absolutely stay here again!"
Breath taking ocean and volcano views! Pool,Close to beaches and everything else

Modern 3 Bedroom Family Friendly Kihei Home Near Beach

9.8 out of 10, Exceptional, (141)
"Perfect location and great place to stay to enjoy Kihei and Wailea. Highly recommend "
Modern 3 Bedroom Family Friendly Kihei Home Near Beach

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

9.8 out of 10, Exceptional, (7)
"We could not be more grateful for our experience in this home. Steps from our lawn was a beautiful beach with unforgettable sunsets on the beach or the fully open air lanai. The home was perfectly and newly appointed, spotless, and comfortable. The management team facilitated an easy check in and also checked in while we were there. Thank you! We’ll be bac!"
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

10.0 out of 10, Exceptional, (30)
"The stay was so good that we already booked for two weeks next year!!"
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

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

9.8 out of 10, Exceptional, (130)
"Love the location, close to beach but you will need a car. Pool is great for adults and kids, it has nice steps at either end. Lots of stairs so be aware, fine for us but maybe not for everyone.Best view ever and sunsets are spectacular!we loved it. "
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

10.0 out of 10, Exceptional, (66)
"stayed for one week with family and enjoyed the place very much. The host is very attentive and quick to respond to all questions/requests. We will come back."
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

Private Home, Saltwater Pool in Favorite South Kihei Neighborhood

9.8 out of 10, Exceptional, (8)
"The place was clean, comfortable, and situated on a quiet street. The beach chairs, toys, and umbrellas were a thoughtful touch. Great choice for a family with nearby beaches, shopping and restaurants. The salt water pool was great and the outdoor shower was convenient. Unfortunately, it was not heated as advertised in Vrbo. It’s probably doesn’t need heating in summer but was a bit cold in February. The outdoor spaces, especially water features, were so relaxing. If I come back to this area, I...
Private Home, Saltwater Pool in Favorite South Kihei Neighborhood
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 Kihei

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (780)
"Property was lovely and we especially appreciated the surprise welcome gift that was waiting for us. Pool was well maintained. It felt a little small for the number of units but we never had a problem finding lounges to sit in. "
The price is AED 2,469
AED 2,913 total
includes taxes & fees
20 Mar - 21 Mar
Aston Maui Hill

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (511)
"A beautiful property with a very nice unit. The check inwas very easy. The beach was wonderful with a spectacular view. You wont be disappointed. "
Wailea Ekahi - CoralTree Residence Collection

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (695)
"Great location, remodeled and clean. "
Wailea Grand Champions - CoralTree Residence Collection
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.