South Maui Condos Permitted for Short-Term Rental

South Maui comprises the towns of Kihei, Maalaea, Makena, and Wailea. Being on the leeward side of Mount Haleakala, it is drier and sunnier than the rest of Maui. With the predictable perfect climate, visitors can fully enjoy the spectacular beauty of the mile-long white sandy crescent-shaped shores, explore the lava fields, and participate in the many water activities available in the area.  

South Maui is one of the top two most popular tourist destinations on the island region of Maui. Instead of hotel-style resorts, the area has a great selection of vacation Condo rentals that guests who prefer a more private relaxation would surely love.

Being locals of Maui, the Maui Property Team has extensive knowledge and understanding of which condo units in the area are included in the permitted short-term rental classification. Contact us today! You may also visit our website to search for the best rental condo. Our website is so easy to use, and you can also save searches and get daily email alerts as new listings become available.

FAQs

View All Latest South Maui Condos Permitted for Short Term Rental

10 WAILEA EKOLU Pl Unit 1304, Kihei image
10 WAILEA EKOLU Pl Unit 1304, Kihei — Wailea Ekolu $1,999,900

Absolutely spectacular 180 degree ocean view with views of Kaho'olawe, Molokini Crater, Lanai, West Maui Mountains and on a clear day, Molokai. Watch the whales play from...

  • 1 Beds
  • 2 Baths
  • 398921 MLS
  • Wailea Ekolu Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

115 N Kihei Rd Unit A14, Kihei image
115 N Kihei Rd Unit A14, Kihei — Kihei Sands $869,000

Welcome to Kihei Sands! This super quaint and modern ground floor unit was completely remodeled in 2020 with new tile flooring throughout, custom designed kitchen cabinet...

  • 1 Beds
  • 1 Baths
  • 398853 MLS
  • Kihei Sands Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

2695 S Kihei Rd Unit 7-105, Kihei image
2695 S Kihei Rd Unit 7-105, Kihei — Kamaole Sands $995,000

This 1 bedroom, 2 bathroom condo at Kamaole Sands has ground floor convenience, a large lanai, and a picturesque location within the middle of the inner court, all of the...

  • 1 Beds
  • 2 Baths
  • 398803 MLS
  • Kamaole Sands Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of PMI Maui

Listing courtesy of PMI Maui.

12 S Kihei Rd Unit F2, Kihei image
12 S Kihei Rd Unit F2, Kihei — Maalaea Surf $1,649,500

This unit is truly turnkey! A complete $300K remodel was done in 2021 and no expense was spared. Luxury sub-zero and Wolf appliances, built in wine refrigerator, Fleetwoo...

  • 1 Beds
  • 1 Baths
  • 398795 MLS
  • Maalaea Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

2430 S Kihei Rd Unit 617, Kihei image
2430 S Kihei Rd Unit 617, Kihei — Royal Mauian $1,999,900

imagine opening your eyes to the beauty of the Blue Pacific Ocean with the sun peeking over Haleakala. One of Royal Mauian’s finest residences with panoramic ocean views....

  • 2 Beds
  • 2 Baths
  • 398752 MLS
  • Royal Mauian Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui Palms Realty LLC

Listing courtesy of Maui Palms Realty LLC.

2191 S Kihei Rd Unit 3321, Kihei image
2191 S Kihei Rd Unit 3321, Kihei — Maui Vista $749,000

Delightful garden view condo on the third floor of the quietest building in the popular Maui Vista Resort. This successful vacation condo places you right where you want...

  • 1 Beds
  • 1 Baths
  • 398738 MLS
  • Maui Vista Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Island Sotheby's Int'l Rlty(M)

Listing courtesy of Island Sotheby's Int'l Rlty(M).

938 S Kihei Rd Unit 125, Kihei image
938 S Kihei Rd Unit 125, Kihei — Kauhale Makai $799,000

Kauhale Makai 125 is a ground floor vacation rentable unit in North Kihei. It's a wonderful family friendly complex with a swimming pool, hot tub, BBQ area, putting green...

  • 1 Beds
  • 1 Baths
  • 398676 MLS
  • Kauhale Makai Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3200 WAILEA ALANUI Dr Unit 1501, Kihei image
3200 WAILEA ALANUI Dr Unit 1501, Kihei — Palms At Wailea I $2,100,000

Welcome to this stunning ground floor condo located on the highly coveted center court of the Palms at Wailea. You'll enjoy gorgeous Ocean views from your King bed in an ...

  • 1 Beds
  • 2 Baths
  • 398670 MLS
  • Palms At Wailea I Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

2695 S Kihei Rd Unit 8-101, Kihei image
2695 S Kihei Rd Unit 8-101, Kihei — Kamaole Sands $910,000

This wonderful ground floor, 1 bedroom, 2 bath, furnished unit is positioned away from the hustle & bustle of South Kihei Road, while still providing occupants with easy ...

  • 1 Beds
  • 2 Baths
  • 398664 MLS
  • Kamaole Sands Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

12 S Kihei Rd Unit G8, Kihei image
12 S Kihei Rd Unit G8, Kihei — Maalaea Surf $1,695,000 ▼

Ocean Views, Soaring Ceilings and Quality Finishes! Ma'alaea Surf is a low density, authentic Polynesian resort on Sugar Beach. Enjoy miles of Sugar Beach from your door...

  • 2 Beds
  • 2 Baths
  • 398650 MLS
  • Maalaea Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Keller Williams Realty Maui-Ka

Listing courtesy of Keller Williams Realty Maui-Ka.

3200 WAILEA ALANUI Dr Unit 2104, Kihei image
3200 WAILEA ALANUI Dr Unit 2104, Kihei — Palms At Wailea I $1,890,000 ▼

Discover a retreat shaped by nature and inspired by culture. An intriguing blend of restful escapism and unbridled joy throughout this Palms vacation rental unit that emb...

  • 2 Beds
  • 2 Baths
  • 398641 MLS
  • Palms At Wailea I Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

2777 S Kihei Rd Unit A212, Kihei image
2777 S Kihei Rd Unit A212, Kihei — Maui Kamaole $1,999,999 ▼

Spectacular ocean views from this front row 2 bedroom, 2 bathroom Maui Kamaole. The unit has been fully remodeled with custom kitchen and baths, cabinets, counter tops, f...

  • 2 Beds
  • 2 Baths
  • 398597 MLS
  • Maui Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1032 S Kihei Rd Unit A-201, Kihei image
1032 S Kihei Rd Unit A-201, Kihei — Maui Sunset $1,495,000

Remodeled instagrammable and pinterest-themed condo boasts 2-bedroom, 2-bathroom with an extra studio guest room with its own queen bed. Enjoy nearly 1,000 square feet o...

  • 2 Beds
  • 2 Baths
  • 398583 MLS
  • Maui Sunset Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

3300 Wailea Alanui Dr Unit 39D, Kihei image
3300 Wailea Alanui Dr Unit 39D, Kihei — Wailea Ekahi Iii $1,765,000

Wow! Have you ever walked into a place and just know it was the one? Between the Venetian plaster walls and natural lauhala and bamboo accents on the vaulted ceilings, th...

  • 1 Beds
  • 1 Baths
  • 398574 MLS
  • Wailea Ekahi Iii Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of REMAX Resort Realty

Listing courtesy of REMAX Resort Realty.

938 S Kihei Rd Unit 109, Kihei image
938 S Kihei Rd Unit 109, Kihei — Kauhale Makai $975,000

Spacious 2 bedroom condo located in an oceanfront building. Set in a tropical oasis, this ground floor condo has privacy and partial ocean views. The location is on the...

  • 2 Beds
  • 2 Baths
  • 398551 MLS
  • Kauhale Makai Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Sunny Maui Vacations

Listing courtesy of Sunny Maui Vacations.

61 N Kihei Rd Unit 9, Kihei image
61 N Kihei Rd Unit 9, Kihei — Kihei Kai $1,100,000

Enjoy this stunning 1 bed 1 bath oasis on Maui's south shore. Situated direct ocean-front on sugar beach in north Kihei, this boutique condo complex is the perfect place ...

  • 1 Beds
  • 1 Baths
  • 398543 MLS
  • Kihei Kai Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-Ku

Listing courtesy of Coldwell Banker Island Prop-Ku.

2777 S Kihei Rd Unit M202, Kihei image
2777 S Kihei Rd Unit M202, Kihei — Maui Kamaole $1,499,900

Excellent remodel and quiet location near the back of the complex. This 2 bedroom, 2 bathroom unit sits in one of the newest buildings and has been very nicely updated wi...

  • 2 Beds
  • 2 Baths
  • 398493 MLS
  • Maui Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

2495 S Kihei Rd Unit 206, Kihei image
2495 S Kihei Rd Unit 206, Kihei — Kihei Kai Nani $929,000

Looking for the perfect vacation rental or a second home? Look no further than hotel zoned, Kihei Kai Nani #206! This upgraded top floor corner unit with extra windows, b...

  • 1 Beds
  • 1 Baths
  • 398448 MLS
  • Kihei Kai Nani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of eXp Realty

Listing courtesy of eXp Realty.

3800 WAILEA ALANUI Dr Unit G201, Kihei image
3800 WAILEA ALANUI Dr Unit G201, Kihei — Wailea Beach Villas $9,995,000 ▼

Wailea's Finest Ocean Front Development Wailea Beach Villas! Rare opportunity to own a 3 Bedroom and 3.5 Bath Villa with dramatic Ocean Views! The elegant and spacious 2,...

  • 3 Beds
  • 3.5 Baths
  • 398409 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop-KP

Listing courtesy of Coldwell Banker Island Prop-KP.

3600 WAILEA ALANUI Dr Unit 905, Kihei image
3600 WAILEA ALANUI Dr Unit 905, Kihei — Wailea Elua I A $5,250,000

Are you looking for a vacation rentable condo (check) in a gated (check) Wailea (check) oceanfront complex (check) with 3 bedrooms (check) and over 1,600 square feet (che...

  • 3 Beds
  • 2 Baths
  • 398351 MLS
  • Wailea Elua I A Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Island Sotheby's Int'l Rlty(W)

Listing courtesy of Island Sotheby's Int'l Rlty(W).

760 S Kihei Rd Unit 427, Kihei image
760 S Kihei Rd Unit 427, Kihei — Menehune Shores $1,349,000 ▼

Elegantly appointed remodeled 2 bedroom / 2 bath unit located on the 4th floor with awesome ocean views. Stunning end-unit with integrated air conditioning with nearly 90...

  • 2 Beds
  • 2 Baths
  • 398347 MLS
  • Menehune Shores Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

4850 Makena Alanui Rd Unit C106, Kihei image
4850 Makena Alanui Rd Unit C106, Kihei — Makena Surf $4,785,000 ▼

Enjoy breathtaking unobstructed ocean, outer island, and sunset views from this extra-large, elegantly renovated, two-bedroom, two-bath Makena Surf condo! This 1,600 squ...

  • 2 Beds
  • 2 Baths
  • 398293 MLS
  • Makena Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Hawaii Life (W)

Listing courtesy of Hawaii Life (W).

4850 MAKENA ALANUI Rd Unit G303, Kihei image
4850 MAKENA ALANUI Rd Unit G303, Kihei — Makena Surf $4,000,000

This RARE and stunning location directly on the ocean has breathtaking views of the Makena coastline, Molokini and Kahoolawe. Beautiful natural light fills the living are...

  • 2 Beds
  • 2 Baths
  • 398224 MLS
  • Makena Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Equity One Real Estate Inc (P)

Listing courtesy of Equity One Real Estate Inc (P).

2777 S Kihei Rd Unit M109, Kihei image
2777 S Kihei Rd Unit M109, Kihei — Maui Kamaole $1,099,000

Are you looking for an immaculate vacation rental in one of the best locations on Maui? You found it! Maui Kamaole M109 is at the top of the complex; and this is the newe...

  • 1 Beds
  • 2 Baths
  • 398212 MLS
  • Maui Kamaole Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

3800 WAILEA ALANUI Blvd Unit B101, Kihei image
3800 WAILEA ALANUI Blvd Unit B101, Kihei — Wailea Beach Villas $14,990,000

THE BEACHFRONT VILLA offers you a phenomenal opportunity to own "the one and only" Direct Ocean Front Villa currently on the market with unobstructed ocean views @ Wailea...

  • 3 Beds
  • 3.5 Baths
  • 398180 MLS
  • Wailea Beach Villas Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Compass

Listing courtesy of Compass.

1002 S Kihei Rd Unit 305, Kihei image
1002 S Kihei Rd Unit 305, Kihei — Waipuilani $565,000 ▼

An Island Oasis found in Kihei at Waipuilani. This one-bedroom, furnished condo sits on the third floor, allowing the ocean breeze to flow freely through the floor-to-cei...

  • 1 Beds
  • 1 Baths
  • 398017 MLS
  • Waipuilani Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Maui Property LLC

Listing courtesy of Maui Property LLC.

145 N Kihei Rd Unit 328, Kihei image
145 N Kihei Rd Unit 328, Kihei — Sugar Beach Resort $1,250,000 ▼

Another Fantastic "Remodeled" BEACHFRONT condo located at Sugar Beach Resort. Remodel includes: Green Granite Countertops, Beach Style tile floors, Bathroom renovation in...

  • 1 Beds
  • 1 Baths
  • 398100 MLS
  • Sugar Beach Resort Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

1993 S Kihei Rd Unit 504, Kihei image
1993 S Kihei Rd Unit 504, Kihei — Island Surf $695,000

Island Surf 504 allows short term rentals and features excellent ocean views. Enjoy watching surfers and daily Sunset views from your lanai. The Cove surf-break directly...

  • 1 Beds
  • 1 Baths
  • 397720 MLS
  • Island Surf Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Berkshire Hathaway Maui Prop-W

Listing courtesy of Berkshire Hathaway Maui Prop-W.

2960 S Kihei Rd Unit 403, Kihei image
2960 S Kihei Rd Unit 403, Kihei — Mana Kai $2,175,000 ▼

When it comes to ultimate beach front living, LOCATION is everything. Mana Kai sits directly on south Maui's famous Keawekapu Beach which extends for almost two miles thr...

  • 2 Beds
  • 2 Baths
  • 397701 MLS
  • Mana Kai Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of eXp Realty

Listing courtesy of eXp Realty.

3550 Wailea Alanui Dr Unit E4, Kihei image
3550 Wailea Alanui Dr Unit E4, Kihei — Andaz Residences $12,750,000 ▼

Andaz Residences E4 offers a rare and unique opportunity for luxurious modern living in your ocean view, 3 bedroom, 4 bath private penthouse with full access to all Andaz...

  • 3 Beds
  • 4 Baths
  • 397631 MLS
  • Andaz Residences Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Royal Realty LLC

Listing courtesy of Royal Realty LLC.

63 Hoolei Cir Unit B2, Kihei image
63 Hoolei Cir Unit B2, Kihei — Hoolei $6,250,000

Location, location, location! Epic ocean views and one of the finest villas in the community make Ho'olei 63-2 an exclusive and highly desired opportunity. The Maile floo...

  • 3 Beds
  • 3.5 Baths
  • 396726 MLS
  • Hoolei Bldg.
  • ACTIVE Status
  • Fee Simple Tenure
Courtesy of Coldwell Banker Island Prop(S)

Listing courtesy of Coldwell Banker Island Prop(S).

Useful Home Searches & Information

Maui Condos Permitted for Short Term Rental

Popular Maui Area Home Search

Current Maui Market Reports

Home Search by Maui School District