South Homes with Leasehold Land tenure

Welcome to Kihei, a vibrant gem nestled on the stunning shores of Maui, Hawaii. Known for its breathtaking beaches, warm sunshine, and laid-back island lifestyle, Kihei is the perfect destination for those seeking a slice of paradise. With its picturesque ocean views and a plethora of outdoor activities, this charming town offers an idyllic setting for both residents and visitors alike.

In Kihei, you’ll find a unique real estate opportunity with homes on leasehold land. This type of tenure allows buyers to enjoy the benefits of owning a home while leasing the land it sits on, often at a more affordable price point. Leasehold properties can be an excellent choice for those looking to invest in the Hawaiian lifestyle without the high costs typically associated with freehold properties.

Kihei boasts an array of amenities, including local shops, delightful eateries, and recreational options such as snorkeling, surfing, and hiking. The warm, inviting community is known for its friendly atmosphere, making it easy to forge connections with neighbors and fellow residents.

With its stunning sunsets and vibrant culture, Kihei is more than just a place to live; it’s a lifestyle. Whether you’re looking for a cozy beach cottage or a modern condo, the leasehold homes in this area offer a fantastic opportunity to immerse yourself in the beauty and charm of Maui. Experience the magic of Kihei and discover your perfect Hawaiian retreat today!

Newest South Homes with Leasehold Land tenure

$840,000

1 Beds ⋅ 2 Baths ⋅ 410234 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

Experience island living at its finest in this beautifully 1-bedroom, 2-bath condo. It Location at pool side and Ocean View is one of Maui Hill Resorts, best Location the owner Feels.This luxurious condo offers stunning ocean and sunset views, just steps from world-famous Keawakapu Beach and Wailea's finest dining and shopping. Two air conditioning units keep the space cool and comfortable year-round. The primary bedroom includes an ensuite bath and access to a peaceful second lanai surrounded by lush greenery. Enjoy resort-style amenities including a heated pool, jacuzzi, tennis courts, shuffleboard, bocce ball, putting green, and on-site concierge. Whether you're seeking adventure or total relaxation, Maui Hill C-30 is your perfect Maui property. This is a Leasehold property.

2881 S Kihei Rd Unit 30, Kihei

Listing courtesy of Kokua Realty LLC.

$1,149,000

2 Beds ⋅ 2 Baths ⋅ 410134 MLS ⋅ Leasehold Tenure ⋅ Kamaole Nalu BLDG.

Rarely does a two bedroom condominium on Maui's South Shore check every box this completely. Kamaole Nalu 402 sits on the fourth floor of a true oceanfront complex, situated between some of the finest swimming and snorkeling beaches on the island, with uniquely stunning and unobstructed ocean views from the private lanai that simply have to be seen to be appreciated. The 774 square foot interior is well designed and move in ready, with stainless steel appliances, granite countertops, in-unit washer and dryer, dishwasher, air conditioning, and elevator access. The primary bedroom offers a king bed with ensuite bath, and the guest bedroom accommodates a queen and a twin with its own ensuite bath. Offered turn key and currently active in a successful vacation rental program, this property carries hotel zoning — a level of short term rental ability that is increasingly rare on Maui's South Shore. Buyers are encouraged to consult with their real estate professional regarding the evolving regulatory landscape and conduct their own due diligence accordingly. This property is Leasehold.

2450 S Kihei Rd Unit 402, Kihei

Listing courtesy of Sunny Maui Vacations.

$399,000

1 Beds ⋅ 1 Baths ⋅ 409938 MLS ⋅ Leasehold Tenure ⋅ Kealia BLDG.

Hotel zoned and sitting right on the sands of Sugar Beach, Kealia 502 is a charming 1-bedroom, 1-bathroom condo with one of the most coveted views in the complex. Straight on, unobstructed oceanfront from your private lanai. This is not a peek-a-boo glimpse of the water. Wake up to the full expanse of the Pacific, watch golden sunsets melt into the channel every evening, and catch humpback whales breaching just offshore during season. The unit has been thoughtfully updated and lovingly maintained by owners who have taken genuine pride in every detail, and it shows the moment you arrive. A proven vacation rental track record with repeat clients speaks for itself. Resort-style amenities include a swimming pool and BBQ area framed by lush tropical landscaping, all right at the water's edge, plus a covered parking stall to keep your car cool. Ideally located with easy access to nearby restaurants, shops, and outdoor adventures, this is a true home base for everything Maui has to offer. Your slice of Sugar Beach is waiting. This is a leasehold property. Notably, select units within Kealia are in the process of converting from leasehold to fee simple, a positive development that benefits all owners within the complex!

191 N Kihei Rd Unit 502, Kihei

Listing courtesy of eXp Realty.

$947,000

2 Beds ⋅ 2 Baths ⋅ 409683 MLS ⋅ Leasehold Tenure ⋅ Kamaole Nalu BLDG.

Imagine waking up to gentle trade winds, stepping onto your private lanai, and watching the Pacific sparkle as the sun sets over Kamaole Beach. This is daily life at Kamaole Nalu #202 — a beautifully positioned second-floor ocean-view residence that delivers the true essence of South Maui living. Nestled directly between Kamaole Beach Parks I and II, this 2-bedroom, 2-bath condo (774 interior sq ft) offers sweeping panoramic ocean views, legendary sunsets, and effortless beach access. The open-concept layout invites island breezes and natural light throughout, creating a seamless flow from the well-appointed kitchen to the living and dining areas. The expansive private lanai becomes your favorite room — perfect for morning coffee, al fresco meals, whale watching in season, or simply unwinding with a glass of wine as the sky turns golden magenta. Inside, thoughtful island-inspired finishes and comfortable furnishings make this a turn-key retreat that feels like home the moment you arrive. The primary suite offers peaceful king-bed comfort, while the guest room (with queen + twin) easily accommodates family or friends. A convertible sofa sleeper in the living area means the unit comfortably sleeps six — ideal for personal use or generating strong vacation rental income. The property is currently professionally managed by Ali'i Resorts, one of Maui’s most respected and experienced short-term rental management companies. This means everything is already handled seamlessly — from bookings and guest services to maintenance and marketing — delivering peace of mind and proven performance for owners who want hassle-free ownership and reliable income. Kamaole Nalu itself is one of South Kihei’s most desirable oceanfront complexes, with a large oceanfront pool, tropical grounds, gas barbecues, free parking, and direct beach access. You’re minutes from Wailea’s golf, shopping, and dining, yet right in the heart of everything Kihei offers — restaurants, markets, snorkeling, paddleboarding, and year-round beach walks. This property sits in the hotel zone, so it is not subject to Bill 9 and remains a fully legitimate short-term rental (STR). Combined with its prime location and proven appeal, it offers excellent flexibility — whether you want a personal Maui getaway, a full-time residence, or a high-performing investment. Kamaole Nalu #202 is more than a condo. It’s your slice of the Maui lifestyle you’ve been dreaming about — ready for you to enjoy, share, or rent from day one. Note: This is a leasehold property.

2450 S Kihei Rd Unit 202, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$639,000

1 Beds ⋅ 2 Baths ⋅ 409619 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

Tucked into the lush tropical grounds of Maui Hill, Unit 107—lovingly known as the “Honeymoon Suite”—captures the warmth, romance, and easy rhythm of South Maui living. This spacious 1-bedroom, 2-bath residence offers over 800 square feet of island comfort, filled with natural light, gentle trade winds, and beautiful ocean views that invite you to slow down and savor each moment. Thoughtfully designed for relaxed indoor-outdoor living, the condo features expansive lanais perfect for morning coffee, sunset dining, or unwinding after a day at the beach. The open, airy feel and welcoming ambiance create a true Maui retreat infused with aloha. Large bedroom features California king bed and tasteful furnishings. Maui Hill is a beloved South Maui property known for its beautifully maintained tropical grounds and exceptional resort-style amenities, including a heated pool and hot tub, tennis courts, putting green, bocce ball, BBQ areas, and more. Ideally located near the Kihei Boat Ramp and the golden sands of Keawakapu Beach, you’re also just minutes from the restaurants, galleries, boutique shopping, and championship golf courses of Wailea. Whether you’re searching for a peaceful island escape, a cherished vacation home, or a popular rental opportunity, Maui Hill 107 offers the perfect blend of comfort, charm, and the unmistakable spirit of Maui. This is a Leasehold property

2881 S Kihei Rd Unit 107, Kihei

Listing courtesy of Hawaii Life (W).

$699,900

2 Beds ⋅ 2 Baths ⋅ 409371 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

Well kept and nicely appointed vacation rental located near the top of the complex. This is a very spacious 2 bed, 2 bath with an open floor plan that appeals to visitors. The south Maui location offers restaurants, shopping, resort golf courses and beautiful beaches in close proximity to the condo. Call your favorite REALTOR® to schedule a private showing today. This is a Leasehold property.

2881 S Kihei Rd Unit 100, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$949,000

2 Beds ⋅ 2 Baths ⋅ 409289 MLS ⋅ Leasehold Tenure ⋅ Kamaole Nalu BLDG.

Experience oceanfront living in South Kihei at Kamaole Nalu 301, a beautifully positioned 2-bedroom, 2-bath condo offering stunning ocean views and an unbeatable beachfront location. Situated on the third floor of this intimate six-story oceanfront complex, the unit features an open living and dining area that flows seamlessly to a private lanai where you can enjoy views of the Pacific, spectacular sunsets, and seasonal whale watching. The spacious floor plan comfortably accommodates guests with a King in the primary suite, twin beds in the guest bedroom, and a sleeper sofa in the living area. The fully equipped kitchen makes it easy to prepare meals at home, while large windows and sliding doors invite in the natural light and refreshing trade winds. Kamaole Nalu is ideally located directly between Kamaole Beach Park I and II, offering immediate access to some of South Maui's best swimming, snorkeling, and sandy beaches. Resort amenities include an oceanfront pool, BBQ area, elevator access, and convenient parking. Just across the street you'll find Kihei's vibrant beach lifestyle with restaurants, shops, and a local grocery store. Whether you're looking for a personal Maui retreat or a strong vacation rental opportunity, this ocean-view condo offers the perfect blend of location, comfort, and island living. This is a leasehold property.

2450 S Kihei Rd Unit 301, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$750,000

2 Beds ⋅ 2 Baths ⋅ 409109 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

This ground floor 2-bedroom, 2-bath condo checks all the boxes—ocean views, a spacious layout, and one of the best locations in South Kihei. Step out onto your large front lanai (accessible from both the living room and primary bedroom) and take in the tropical setting with a peek of the Pacific—it’s the perfect spot for morning coffee or sunset cocktails. Inside, you’ll find an open, comfortable layout with granite countertops, plenty of space to relax, and a great separation between bedrooms. The second bedroom even has its own private lanai, giving guests or family their own peaceful retreat. Maui Hill is known for its laid-back, resort-style vibe—complete with a large pool, hot tub, tennis courts, putting green, shuffleboard, bocce ball, and everyone’s favorite… mai tai nights with music by the pool ?? You’re perfectly located just across from the Kihei boat ramp and right between Kam III and Keawakapu Beach—ideal for beach days, snorkeling, turtles, and winter whale watching. Whether you’re looking for a personal getaway or a successful vacation rental, this one delivers. Maui Hill is a leasehold property.

2881 S Kihei Rd Unit 33, Kihei

Listing courtesy of Real Broker.

$699,000

2 Beds ⋅ 2 Baths ⋅ 408982 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

Welcome to this cozy 2-bedroom, 2-bath downstairs residence in the highly desirable Maui Hill community. Quietly positioned at the top of the complex, this inviting unit enjoys a peaceful setting with partial ocean views and refreshing island breezes. The spacious covered lanai is perfect for relaxing or entertaining while taking in Maui's year-round tropical weather. Inside, you'll find a comfortable and functional layout ideal for full-time living, a second home, or vacation rental potential. Maui Hill features 140 units thoughtfully spread across more than 12 lush acres, offering a low-density, resort-style atmosphere. Ideally located directly across the street from Keawakapu Beach-one of South Maui's most coveted stretches of sand-you're just moments from swimming, snorkeling, and sunset strolls. Some of Maui Hill's amenities include: a large heated swimming pool, spa, multiple barbecue areas , tennis court, shuffleboard court, putting green, and more. Shopping, dining, golf, and additional beaches are all just minutes away, making this an exceptional South Maui location. This is a leasehold property with a master lease in place through 2064. The 3-bedroom unit directly above is also currently available for purchase-presenting a rare opportunity for expanded living or investment potential. Experience the best of island living at Maui Hill.

2881 S Kihei Rd Unit 93, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$848,000

2 Beds ⋅ 2 Baths ⋅ 408804 MLS ⋅ Leasehold Tenure ⋅ Maui Hill BLDG.

Welcome to Maui Hill 59, a rarely offered condo in one of the premier South Kihei resorts across from Keawakapu beach. Enjoy beautiful morning sunrises over Haleakala from the oversized lanai with partial ocean views. This spacious 2 bedroom 2 bath unit has many recent upgrades including a full kitchen remodel in May 2024. Features include an open floor plan, stainless steel appliances, open shelving, and quartz countertops. Offered fully furnished and completely turnkey, this successful vacation rental is larger than your average condo at 1,115 square feet. With a south facing lanai off the living room and a garden view lanai off the 2nd bedroom this unit offers fantastic indoor and outdoor living areas. Close proximity to beaches, shopping, and restaurants makes this a great residential option. This is a leasehold property with master lease through 2064. Seller is listing agent and holds an active Real Estate license in the state of Hawaii. Contact your favorite real estate professional to schedule a showing!

2881 S Kihei Rd Unit 59, Kihei

Listing courtesy of Real Broker.

$349,000

1 Beds ⋅ 1 Baths ⋅ 408339 MLS ⋅ Leasehold Tenure ⋅ Kealia BLDG.

Kihei beachfront living at its finest! This beautifully remodeled Kealia condo is a highly sought-after vacation rental and an exceptional opportunity for both personal enjoyment and investment. Thoughtfully redesigned from top to bottom, the unit features an upgraded kitchen and bathroom, tile flooring throughout, and well-appointed furnishings that create additional storage while maintaining an open, airy floor plan. Expansive ocean views and year-round sunsets take center stage, offering a true front-row seat to Maui’s natural beauty. Kealia Resort is perfectly positioned on five miles of sandy beach stretching to Maalaea, ideal for long walks, swimming, and whale watching in season. Don't forget about those stunning sunsets, a perfect end to each day. Centrally located, this oceanfront community provides easy access to all that Maui has to offer, including world-class shopping, dining, and golf in nearby Wailea. A turnkey beachfront condo in one of South Maui’s most desirable coastal settings—this is island living done right. This is a leasehold condo.

191 N Kihei Rd Unit 402, Kihei

Listing courtesy of Hawaii Life (W).

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.