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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

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

866 reviews

5.0 / 5

Great apartment! The beach chairs and umbrellas were a huge plus. Nice location super close to restaurants and the beach.

K
KatieStayed in September 2026
5.0 / 5

Great stay in a great area. Beautiful walk around the building towards the beach

S
SanjayStayed in September 2026
5.0 / 5

A perfect place for our first trip to Maui!

C
ColleenStayed in September 2026
5.0 / 5

Had a great stay at Matt’s place! He was super super responsive and the place had so many amenities, even had aloe for my sunburn. Close to some good eats and grocery stores, located in a central area.

J
JacquelineStayed in September 2026
5.0 / 5

Great few days in Kehei. The condo was a fantastic base and everything we needed was there. Super comfy bed - better than a hotel!

R
RosannaStayed in September 2026
5.0 / 5

Amazing stay in Kihei! Perfect for 2-3 people. Would book again!

B
BrookeStayed in September 2026
5.0 / 5

This home was beautiful! I would stay here again! My kids really enjoyed themselves and so did we

N
NakoaStayed in September 2026
5.0 / 5

Le logement est bien situé pour découvrir l’île. Tout était conforme et propre. Nous sommes très contents de notre séjour.

S
SarahStayed in September 2026
5.0 / 5

We had such a wonderful stay at Matt’s place! He was incredibly responsive and friendly throughout our visit. Self check‑in was seamless, and the front desk staff were so sweet and welcoming. The location was perfect, and the space truly felt like home. We’d absolutely stay here again, highly recommend!

S
SavannahStayed in September 2026
5.0 / 5

Great location and a very pleasant stay. Really enjoyed my time here!

S
ShiqianStayed in September 2026
5.0 / 5

Great apartment! The beach chairs and umbrellas were a huge plus. Nice location super close to restaurants and the beach.

K
KatieStayed in September 2026
5.0 / 5

Great stay in a great area. Beautiful walk around the building towards the beach

S
SanjayStayed in September 2026
5.0 / 5

A perfect place for our first trip to Maui!

C
ColleenStayed in September 2026
5.0 / 5

Had a great stay at Matt’s place! He was super super responsive and the place had so many amenities, even had aloe for my sunburn. Close to some good eats and grocery stores, located in a central area.

J
JacquelineStayed in September 2026
5.0 / 5

Great few days in Kehei. The condo was a fantastic base and everything we needed was there. Super comfy bed - better than a hotel!

R
RosannaStayed in September 2026
5.0 / 5

Amazing stay in Kihei! Perfect for 2-3 people. Would book again!

B
BrookeStayed in September 2026
5.0 / 5

This home was beautiful! I would stay here again! My kids really enjoyed themselves and so did we

N
NakoaStayed in September 2026
5.0 / 5

Le logement est bien situé pour découvrir l’île. Tout était conforme et propre. Nous sommes très contents de notre séjour.

S
SarahStayed in September 2026
5.0 / 5

We had such a wonderful stay at Matt’s place! He was incredibly responsive and friendly throughout our visit. Self check‑in was seamless, and the front desk staff were so sweet and welcoming. The location was perfect, and the space truly felt like home. We’d absolutely stay here again, highly recommend!

S
SavannahStayed in September 2026
5.0 / 5

Great location and a very pleasant stay. Really enjoyed my time here!

S
ShiqianStayed in September 2026

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