Keawakapu Homes with Short Term Rental Allowed

Keawakapu Homes with Short Term Rental Allowed

Welcome to Keawakapu, a hidden gem nestled in the heart of Kihei, Maui. This enchanting neighborhood is renowned for its stunning beaches, vibrant sunsets, and a laid-back atmosphere that embodies the spirit of island living. Keawakapu is particularly favored for its proximity to the pristine shores of Keawakapu Beach, where golden sands meet the turquoise waters of the Pacific Ocean, providing the perfect backdrop for sunbathing, snorkeling, and leisurely strolls along the shore.

In addition to its natural beauty, Keawakapu boasts a charming community with a mix of residential properties, making it an ideal place for both locals and visitors. One of the standout features of this neighborhood is the availability of homes that allow short-term rentals. This unique opportunity makes Keawakapu an attractive option for those looking to invest in a vacation rental or seeking a second home that can generate income. Imagine owning a piece of paradise where you can host guests and share the magic of Maui, all while enjoying the island lifestyle yourself.

The neighborhood is also conveniently located near an array of amenities, including boutique shops, local eateries, and recreational activities. Whether you’re exploring the nearby Wailea resort area or indulging in a sunset dinner at one of the waterfront restaurants, Keawakapu offers a perfect blend of relaxation and adventure.

With its idyllic setting and promising investment potential, Keawakapu is truly a slice of paradise waiting to be discovered. Come experience the allure of this Maui neighborhood and envision your future in this tropical haven!

Newest Keawakapu Homes with Short Term Rental Allowed

$619,900
1 Beds ⋅ 2 Baths ⋅ 410265 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
COMING SOON •BEST PRICED MAUI KAMAOLE• This Unit K-105 is currently being NEWLY RENOVATED and will be available for showings in approximately 3 weeks once the listing becomes Active. 849 SQ FT 1 bed, 2 full bathrooms built in 1999 and renovated in 2026. Fresh Sherwin-Williams Pure White interior paint, BRAND NEW Sputnik dining chandelier, NEW recessed lights, newer cabinets with fully adjustable shelves, melamine interiors and under cabinet lighting. NEW Brushed nickel cabinet and door hardware throughout. Newer stainless steel refrigerator, dishwasher, microwave, and hot water heater. BRAND NEW vinyl plank floors in living room and bedroom. Professionally cleaned tile floors. Newer drapes throughout. 2 full bathrooms, 2 AC units 2 outdoor spaces! Great storage with freshly painted louvered doors and NEW brushed nickel door knobs and pulls! 3 closets in bedroom, ensuite bathroom with two sinks, counter to ceiling mirror, CLEAN shower over tub with tile surround. Furniture and recreation equipment included. BRAND NEW Queen Sofa Sleeper. Second bathroom has tiled shower and counter to ceiling mirror. 1 deeded parking space. Maui Kamaole is the NICEST, NEWER LOW-RISE Complex in a QUIET South Kihei LOCATION bordering Wailea across from the Kihei Boat Ramp and Kamaole Beach Park III. Complex amenities feature: 2 tennis courts, 2 pool spa pavilions, several Weber BBQ areas and gazebos with plenty of tables and chairs. This unit is a GREAT BUY so Please Standby to view the property once it becomes Active. Thank you for your patience!

2777 S Kihei Rd Unit K-105, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$799,000
1 Beds ⋅ 2 Baths ⋅ 410072 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Escape to Paradise at Maui Kamaole Experience the ultimate Maui getaway in this beautiful ground-floor condo, located in the highly sought-after Maui Kamaole resort community. Perfectly situated across the street from Maui's renowned Golden Mile beaches, this tropical retreat places you within easy walking distance of pristine beaches, shops, restaurants, and island activities. Maui Kamaole offers exceptional resort-style amenities, including: • Two sparkling swimming pools • Two relaxing hot tubs • Two tennis courts • Convenient storage areas for paddleboards and kayaks This spacious one-bedroom, two-bathroom condo comfortably accommodates up to four guests and is thoughtfully equipped for both relaxation and convenience. Features include: • New dishwasher • New dryer • New sleeper sofa mattress • Private patio off the primary bedroom • Fully equipped kitchen with generous counter space • Stylish Tommy Bahama furnishings throughout • Charming lanai with elegant wrought-iron patio furniture Start your mornings on the peaceful lanai, coffee in hand, listening to the birds sing as the island awakens around you. Whether you're spending your days at the beach, exploring Maui, or simply unwinding by the pool, this inviting condo offers the perfect blend of comfort, convenience, and tropical charm. Escape to Paradise at Maui Kamaole Experience the ultimate Maui getaway in this beautiful ground-floor condo, located in the highly sought-after Maui Kamaole resort community. Perfectly situated across the street from Maui's renowned Golden Mile beaches, this tropical retreat places you within easy walking distance of pristine beaches, shops, restaurants, and island activities. Maui Kamaole offers exceptional resort-style amenities, including: • Two sparkling swimming pools • Two relaxing hot tubs • Two tennis courts • Convenient storage areas for paddleboards and kayaks This spacious one-bedroom, two-bathroom condo comfortably accommodates up to four guests and is thoughtfully equipped for both relaxation and convenience. Features include: • New dishwasher • New dryer • New sleeper sofa mattress • Private patio off the primary bedroom • Fully equipped kitchen with generous counter space • Stylish Tommy Bahama furnishings throughout • Charming lanai with elegant wrought-iron patio furniture Start your mornings on the peaceful lanai, coffee in hand, listening to the birds sing as the island awakens around you. Whether you're spending your days at the beach, exploring Maui, or simply unwinding by the pool, this inviting condo offers the perfect blend of comfort, convenience, and tropical charm.

2777 S Kihei Rd Unit D103, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$919,000
2 Beds ⋅ 2 Baths ⋅ 409890 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Remote workers and semi-retirees eyeing an escape from the mainland will find a lot to like in F209 at Maui Kamaole. Both the upstairs primary bedroom and the main floor guest bedroom look out toward Haleakala volcano, and with Hawaii running behind the mainland, early mornings come with a front-row seat to the sunrise over the mountain that most people only see on vacation. The guest bedroom doubles naturally as a home office. Three lanais in total catch the light at different times of day, and the whole unit sits in one of the quietest corners of the complex with a private BBQ area just outside the door. At 1,052 square feet the space lives comfortably, the insulated ceiling keeps electric bills lower than most comparable units, and convenient parking means the practical side of daily life here is as easy as it gets. Maui Kamaole spans more than 23 acres of lush tropical landscaping on a hillside directly across from Kamaole Beach Park III, with two pools including a sand-bottom pool, two spas, gas grills, and tennis courts, all within easy reach of Keawakapu Beach, South Maui dining, and the kind of unhurried pace that makes you wonder why you waited this long to make the move. PHL Prime Resort financing is available for this condo! This program helps avoid the higher down payment and rate adjustments associated with vacation rental financing.

2777 S Kihei Rd Unit F209, Kihei

Listing courtesy of eXp Realty.

$1,590,000
2 Beds ⋅ 2 Baths ⋅ 409801 MLS ⋅ Fee Simple Tenure ⋅ Hale Hui Kai BLDG.
Hale Hui Kai is a true hidden gem on Keawakapu Beach — a boutique oceanfront complex in an unbeatable location. From the moment you step into its quiet, lush walkways, you’re greeted with the timeless charm of old Hawaiiana. This beautifully remodeled ground floor two bedroom, two-bath residence features a thoughtful, creative design throughout. The spacious lanai offers a pleasant view — not fully oceanfront, but with a lovely glimpse of the water that reminds you just how close you are to the shoreline. Just steps away from one of South Maui’s best beaches, Keawakapu! The primary suite showcases a stunning tiled shower paired with bamboo cabinetry, while the hall bath features an equally striking tub surround with meticulous detailing. The kitchen is an entertainer’s delight, blending granite countertops, and bamboo cabinets and a timeless tile floor for a warm, inviting atmosphere. With quality finishes throughout, this unit is the perfect island getaway. If you’re searching for beachfront living in Kihei, this is a must see — just steps from one of the best white sand beaches in the Kihei/Wailea area. Hotel zoned and vacation rentable, this oceanfront complex offers exceptional flexibility—whether you’re seeking rental income, a second home, or the ultimate island living retreat. Keawakapu is the kind of place where locals come to unwind, visitors fall in love with the island, and every day ends with a postcard worthy view. It’s not just a beach—it’s a feeling of pure island living. The Hale Hui kia sits on one of South Maui’s most treasured stretches of coastline. And don’t forget about the world class dining, shopping and golf that awaits just minutes away.

2994 S Kihei Rd Unit 106, Kihei

Listing courtesy of Hawaii Life (W).

$649,900
1 Beds ⋅ 2 Baths ⋅ 409659 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
MASSIVE $225,000 PRICE REDUCTION! This incredible discount reflects Maui's current short-term rental zoning transitions, offering a rare opportunity to acquire a premium, turnkey end unit at Maui Kamaole in South Kihei at an unbeatable value. Following the passage of Bill 9, Maui County officially approved Bill 88 to create a brand-new H-3 / H-4 hotel zoning framework explicitly designed to allow qualifying apartment-zoned resort properties to pursue permanent short-term rental zoning. Maui Kamaole is among the prominent South Maui properties formally listed to pursue this streamlined pathway. In the meantime, short-term rentals remain a fully viable option here until at least January 1, 2031, providing an excellent window for immediate cash flow and personal use. Tucked away from car and foot traffic, this private, ground-level home offers ultimate peace and quiet in a sprawling garden setting bursting with tropical flowers. Enjoy amazing cross breezes thanks to two private outdoor spaces: a front garden lanai and a second walled patio. The spacious interior layout features two full baths and two sofa beds, allowing the living area to seamlessly serve as a second bedroom for guests. Upgraded for modern comfort, the unit boasts two brand-new, energy-efficient mini-split A/C units, a California King bed, newer kitchen appliances, and a built-in water filter and 6 closets. Positioned in a wind-sheltered section with excellent drainage, you will experience protection from storms and no issues with gnats. Steps from your door, enjoy resort amenities like the delightful waterfall pool, jacuzzi, tennis courts, and BBQ areas. Best of all, you are directly across the street from the Kihei boat launch and world-class beaches such as Kamaole III and Keawakapu Beach. Offered completely furnished—including all kitchenware, linens, a fruiting dwarf lime tree, and even beach gear. Truly turn-key and ready for you to move right in or rent out!

2777 S Kihei Rd Unit K101, Kihei

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$949,000
1 Beds ⋅ 1 Baths ⋅ 409650 MLS ⋅ Fee Simple Tenure ⋅ Kihei Surfside BLDG.
Kihei Surfside Unit 209 is OCEANFRONT ON THE ISLAND OF MAUI. GORGEOUS OCEAN VIEWS! Set along South Maui’s treasured shoreline, where seasonal whale watching and sea turtle sightings reflect the natural rhythm of the coast, this contemporary remodeled one-bedroom, one-bath condominium offers an inspiring connection to its surroundings. In the main living area, an entire wall of windows frames expansive views of the Pacific Ocean, lush manicured lawn, and the West Maui Mountains in the distance, filling the home with natural light and beauty. The kitchen features richly veined polished granite countertops and is thoughtfully designed to capture ocean views, opening seamlessly into the living space for an effortless indoor-outdoor flow centered on the scenery beyond. Beyond the interiors, the private lanai becomes an extension of the home itself — a place to begin the morning with coffee or unwind beneath Maui’s unforgettable sunsets. The bedroom features a Cal King bed, while the living area offers additional accommodations with a sleeper sofa. The modern bath features a sleek walk-in shower and the same rich deep-veined granite as in the kitchen. Two split air-conditioners provide comfort throughout the year. At Kihei Surfside, residents and guests enjoy an exceptional collection of resort-style amenities, including oceanfront BBQ areas, a beautifully maintained lawn with putting green, and a renovated pool overlooking the sea — all designed to embrace Maui’s outdoor lifestyle. Just steps away lies world-renowned Keawakapu Beach, celebrated for its golden sand, blue waters, exceptional snorkeling, swimming, and diving. Paddleboards, kayaks, and surf gear are conveniently available nearby. Moments away, Wailea offers world-class golf, luxury resorts, acclaimed dining, and premier shopping at The Shops at Wailea, creating a lifestyle that effortlessly blends relaxation, recreation, and sophistication. Hotel-zoned with a STRONG VACATION RENTAL HISTORY and exceptional guest reviews, Unit 209 offers a compelling opportunity for those seeking a primary residence, a vacation home, and/or investment potential. The choice is yours. Come experience the beauty and ease of life by the sea... at one of Maui’s most coveted oceanfront locations. Maui Beach Life!

2936 S Kihei Rd Unit 209, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

$1,450,000
2 Beds ⋅ 2 Baths ⋅ 409623 MLS ⋅ Fee Simple Tenure ⋅ Hale Hui Kai BLDG.
Beach Front! Hidden along the renowned mile long white sandy beach of Keawakapu, Hale Hui Kai is a charming, low rise beachfront complex that captures the timeless feeling of Old Hawaii. Lush tropical landscaping and open air walkways welcome you into this well maintained oceanfront retreat, where the relaxed Maui lifestyle takes center stage. From the ground floor garden access to the pool and beach, making it effortless to enjoy swimming, paddleboarding, snorkeling, and relaxing by the water. Evenings are spent taking in Maui’s spectacular sunsets. Conveniently located near Wailea’s world class golf courses, shopping, dining, and resort amenities, the property also offers seasonal whale watching during the winter months right offshore. This two bedroom, two bath residence features a partial ocean view and is offered fully furnished, excluding the Sellers artwork and paintings. Interior features are granite counter tops, updated cabinetry, central AC, and an in unit washer and dryer, with an additional community laundry facility available onsite. Whether you are seeking the perfect Maui getaway, a beachfront primary or a second home, or a vacation rental, this is a rare opportunity to own a beachfront condominium on Maui. The $164,000 assessment for major renovations to the complex has been paid by the Seller in advance.

2994 S Kihei Rd Unit 301, Kihei

Listing courtesy of Island Sotheby's International Realty(W).

$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).

$849,900
1 Beds ⋅ 2 Baths ⋅ 409278 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Front Row, Ocean Views it does not get much better than this. This one bedroom, two bathroom unit has been upgraded with bamboo cabinet doors, luxury vinyl floors, and split system AC. Close proximity to Kamaole One Beach Park and Keawakapu Beach. Maui Kamaole is a resort style community with two pools, 2 hot tubs, two tennis courts and Kayak and paddle board storage for owners. Call your favorite REALTOR to schedule a private showing today.

2777 S Kihei Rd Unit G101, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$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.

$799,000
1 Beds ⋅ 2 Baths ⋅ 409073 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Large & Unique one bedroom plus a den. There are only 14 in the complex like this one. Nicely remodeled with new kitchen cabinets, granite kitchen counter tops, luxury vinyl floors in the bedroom and den and porcelain tile floors in the hallway, kitchen and dining room. Quiet location, but close proximity to the upper pool & tennis courts. Maui Kamaole offers 2 pools, 2 hot tubs, 2 tennis courts and owners storage for paddle boards and kayaks. The beaches just across the street are stellar white sand beaches and the complex is within 10 minutes of numerous resort golf courses. Do not miss this one, call your favorite REAL TOR to schedule a private showing today.

2777 S Kihei Rd Unit F103, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

Start Your Search