Hawaii Vacation Homes

Vacation Rentals In South Maui

Professionally managed Maui vacation rentals delivering exceptional guest experiences and personalized care

Available properties

Welcome To Hawaii Vacation Homes

We are your locally based source for South Maui vacation rentals, offering thoughtfully maintained condos and homes in Kihei and Wailea. Every stay comes with seamless booking, responsive support, and the comfort of a place cared for like our own.

Since 2020, we've delivered consistent quality and stress-free stays, earning hundreds of five-star reviews from guests who return year after year.


Benefits of Booking Direct

Book with us and keep more in your pocket.

  • Best Rates

  • Lower Booking Fees

  • More Flexibility

The Hawaii Vacation Homes Difference

Thoughtful hosting from booking to checkout, on every Maui stay.

Carefully Maintained Homes

Easy, Seamless Arrivals

Personal Hosting With Aloha

Meet Your Hosts

Hawaii Vacation Homes is a locally run team led by Kihei-based host Matt Buck, offering thoughtfully maintained condos and homes across South Maui. Since 2020, we've focused on clean, comfortable stays backed by responsive, personal support, so guests can relax and enjoy the island. Matt holds each home to the same standard he would want as a guest, which is how Hawaii Vacation Homes has earned its reputation for clean, comfortable, and reliable stays.

Reviews

4.9

786 reviews

5.0 / 5

Matt is very responsive and the place is very nice and in a beautiful area. Would stay again! Loved watching tv too while in bed 😝

L
LeilaStayed in July 2026
5.0 / 5

Great little unit, very clean and had all amenities needed! Very nice to have washer/dryer option! The team was incredible and quick to respond when we had questions!

M
MelissaStayed in July 2026
5.0 / 5

Thank you for hosting us. We had an amazing time at your condo.

K
KarlaStayed in July 2026
5.0 / 5

Short walk to the beach, restaurants, & stores. Party of 6 & a bed for everyone. Fun in the sun for everyone!

R
ReginaStayed in July 2026
5.0 / 5

Excellent location close to a fabulous and not crowded beach with beautiful sunsets! Extremely close to many great shops and restaurants. Plenty of bath and beach towels, laundry soap and dishwasher detergent. The place had two sets of full snorkel gear, beach chairs, and boogie boards, giving us plenty to do! I also appreciated the coffee grinder and blender, along with a fully stocked kitchen. Matt was very communicative and responsive and very friendly. I would definitely stay there again!

J
JohnStayed in July 2026
5.0 / 5

Matt's condo is absolutely perfect for a visit to South Maui! Spacious, beautifully decorated, and best of all it has a gorgrous ocean view! You can watch the sunset from your lanai or easily walk right down to the beach. The unit has everything to make a vacation perfect including a beautiful pool and hot tub. We booked a week with him and would recommend this spot to anyone! Communication is great and instructions are clear. Thanks Matt!

B
BethanyStayed in July 2026
5.0 / 5

Overall was a good place to stay, right by the ocean and the pools were fabulous

K
KestynStayed in July 2026
5.0 / 5

We loved staying at Matt and Terry’s place. It was the perfect size and layout for our family of 5. The kitchen was well stocked for us to cook in and the amount of towels and pillows was outstanding. We used the wagon and beach chairs and boogie boards every day. Nice and easy walk to the beach. The AC was great as well since it was pretty humid outside most days. The condo is a quiet end unit, we were so happy with our stay. We also made use of the gym, pool, pickleball courts, and BBQs on site. We highly recommend to any family looking for a chill, beach vacay on Maui.

S
SallyStayed in July 2026
5.0 / 5

This place was comfortable with two relaxing lanais with beautiful views of the water. Grounds are beautifully maintained. Beaches are across the street. Walkable to stores and restaurants. Pool and laundry is a plus. Matt was great to work with - friendly, helpful and quick to respond.

J
JoannaStayed in July 2026
5.0 / 5

Matt's place was perfect! It was exactly like the photos, super clean, comfortable, and very quiet. Matt was very responsive and the office staff was friendly and helpful. The location was excellent with so many great restaurants and businesses nearby. It was very conveniently located by the beach. I would definitely recommend Matt's place and wouldn't hesitate to stay there again.

S
SharonStayed in July 2026
5.0 / 5

Matt is very responsive and the place is very nice and in a beautiful area. Would stay again! Loved watching tv too while in bed 😝

L
LeilaStayed in July 2026
5.0 / 5

Great little unit, very clean and had all amenities needed! Very nice to have washer/dryer option! The team was incredible and quick to respond when we had questions!

M
MelissaStayed in July 2026
5.0 / 5

Thank you for hosting us. We had an amazing time at your condo.

K
KarlaStayed in July 2026
5.0 / 5

Short walk to the beach, restaurants, & stores. Party of 6 & a bed for everyone. Fun in the sun for everyone!

R
ReginaStayed in July 2026
5.0 / 5

Excellent location close to a fabulous and not crowded beach with beautiful sunsets! Extremely close to many great shops and restaurants. Plenty of bath and beach towels, laundry soap and dishwasher detergent. The place had two sets of full snorkel gear, beach chairs, and boogie boards, giving us plenty to do! I also appreciated the coffee grinder and blender, along with a fully stocked kitchen. Matt was very communicative and responsive and very friendly. I would definitely stay there again!

J
JohnStayed in July 2026
5.0 / 5

Matt's condo is absolutely perfect for a visit to South Maui! Spacious, beautifully decorated, and best of all it has a gorgrous ocean view! You can watch the sunset from your lanai or easily walk right down to the beach. The unit has everything to make a vacation perfect including a beautiful pool and hot tub. We booked a week with him and would recommend this spot to anyone! Communication is great and instructions are clear. Thanks Matt!

B
BethanyStayed in July 2026
5.0 / 5

Overall was a good place to stay, right by the ocean and the pools were fabulous

K
KestynStayed in July 2026
5.0 / 5

We loved staying at Matt and Terry’s place. It was the perfect size and layout for our family of 5. The kitchen was well stocked for us to cook in and the amount of towels and pillows was outstanding. We used the wagon and beach chairs and boogie boards every day. Nice and easy walk to the beach. The AC was great as well since it was pretty humid outside most days. The condo is a quiet end unit, we were so happy with our stay. We also made use of the gym, pool, pickleball courts, and BBQs on site. We highly recommend to any family looking for a chill, beach vacay on Maui.

S
SallyStayed in July 2026
5.0 / 5

This place was comfortable with two relaxing lanais with beautiful views of the water. Grounds are beautifully maintained. Beaches are across the street. Walkable to stores and restaurants. Pool and laundry is a plus. Matt was great to work with - friendly, helpful and quick to respond.

J
JoannaStayed in July 2026
5.0 / 5

Matt's place was perfect! It was exactly like the photos, super clean, comfortable, and very quiet. Matt was very responsive and the office staff was friendly and helpful. The location was excellent with so many great restaurants and businesses nearby. It was very conveniently located by the beach. I would definitely recommend Matt's place and wouldn't hesitate to stay there again.

S
SharonStayed in July 2026

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