Kihei Homes with Short Term Rental Allowed

Kihei Homes with Short Term Rental Allowed

Welcome to Kihei, a vibrant coastal gem nestled on the sunny shores of Maui, Hawaii. Known for its stunning beaches, warm climate, and friendly atmosphere, Kihei is the perfect place for those seeking a slice of paradise. With its picturesque landscapes and breathtaking sunsets, this charming town offers a unique blend of relaxation and adventure.

Kihei boasts an array of beautiful homes, many of which are perfect for short-term rentals. This feature makes it an attractive option for investors and vacationers alike, providing an opportunity to enjoy the island lifestyle while generating rental income. Imagine waking up to the sound of waves crashing and the scent of ocean breezes, all while being just minutes away from some of the best beaches in the state.

The neighborhood is dotted with a variety of amenities, including local shops, restaurants, and recreational activities. Whether you’re in the mood for a casual beachside café or a fine dining experience, Kihei has something to satisfy every palate. Outdoor enthusiasts will revel in the abundance of water sports, hiking trails, and nearby golf courses, ensuring there’s never a dull moment.

Community events and cultural festivals are also a staple in Kihei, fostering a strong sense of camaraderie among residents and visitors. With its welcoming vibe and stunning surroundings, Kihei is more than just a place to live; it’s a lifestyle. Explore the possibilities of owning a home in this idyllic neighborhood where short-term rentals are allowed, and embrace the Maui dream today!

Newest Kihei Homes with Short Term Rental Allowed

$695,000
2 Beds ⋅ 2 Baths ⋅ 410717 MLS ⋅ Fee Simple Tenure ⋅ Kihei Resort BLDG.
Fully renovated 2BR/2BA at Kihei Resort, across the street from Waipuilani Beach and a one-minute walk to Kalepolepo Beach Park. Remodeled top to bottom with modern finishes, a fully equipped kitchen, cold AC, high-speed WiFi, and 50" and 55" smart TVs. King primary with step-in shower ensuite; second bedroom with bunk and twin beds; queen sleeper sofa in the living room for extra guests. Covered lanai overlooks lush courtyard grounds, with the resort pool and hot tub a short walk away. Has been professionally managed as a vacation rental; performance history available on request. Owner is listor and holds an active Hawaii real estate license.

777 South Kihei Rd Unit 218, Kihei

Listing courtesy of Luxe Maui Properties LLC.

$485,000
1 Beds ⋅ 1 Baths ⋅ 410520 MLS ⋅ Fee Simple Tenure ⋅ Wailana Kai BLDG.
Discover the perfect Maui getaway at Wailana Kai #102, a ground-floor, boutique hotel-zoned condo located directly across the street from the ocean. Offering the ideal combination of location, comfort, and investment potential, this inviting property is a wonderful opportunity for those looking to enjoy the Maui lifestyle or add a vacation-rental property to their portfolio. Recently renovated and thoughtfully refreshed, the condo features a freshly painted interior, newly purchased furniture, and stylish, easy-care finishes. Tile flooring runs throughout the main living areas, while laminate flooring in the bedroom provides warmth and comfort. A new split-system A/C adds modern convenience and keeps the unit cool and comfortable year-round. One of the highlights is the private lanai, where you can relax and enjoy the tropical surroundings with the ocean and beach just across the street. Start your morning with coffee outdoors, return from a day at the beach to unwind, or enjoy Maui's beautiful sunsets from your own private outdoor space. As a ground-floor unit, this condo offers easy access and a convenient indoor-outdoor lifestyle. The boutique complex also features a refreshing swimming pool, providing another place to relax and enjoy the beautiful Hawaiian weather. With its hotel zoning, ground-floor location, pool, private lanai, recent renovations, new furnishings, and prime location across from the ocean, 34 Wailana Kai offers an exceptional opportunity to own a piece of Maui in a setting designed for enjoying island life. Whether you're looking for a Maui retreat, a vacation-rental opportunity, or a place to call your own in paradise, this charming condo is ready to be enjoyed.

34 Wailana Pl Unit 102, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$535,000
1 Beds ⋅ 1 Baths ⋅ 410505 MLS ⋅ Fee Simple Tenure ⋅ Waiohuli Beach Hale BLDG.
Waiohuli Beach Hale is a small oceanfront complex located in Kihei. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants, and beaches. Additionally, there is a 60 foot solar heated pool, barbecues and shuffleboard located right next to the ocean. Unit #107 is located on the ground floor making trips to the pool or the grill quick and convenient. The condo is being sold fully-furnished, including all of the inventory. The unit has a comfortable layout in a very relaxing environment. A perfect option as a vacation home or rental. There is a common-laundry room on-site. This complex is one of the great finds in South Maui for its affordability and charm. Whale watch (in-season), windsurf, walk the beach and enjoy magnificent sunsets from the manicured grounds. Contact your favorite Realtor today to schedule your showing! This unit has a great short-term rental history, but we encourage any buyers to do their own due diligence on their ability to conduct short term rentals if it is pertinent to their purchase.

49 W Lipoa St Unit 107, Kihei

Listing courtesy of Rentals Maui Inc.

$1,295,000
2 Beds ⋅ 2 Baths ⋅ 410488 MLS ⋅ Fee Simple Tenure ⋅ Kihei Beach BLDG.
Experience the very best of oceanfront South Maui living at Kihei Beach #101, a beautifully renovated, hotel-zoned, ground-floor condominium situated directly on the golden sands of Sugar Beach. Thoughtfully remodeled in 2019, this spacious end-unit, two-bedroom, two-bath residence offers an exceptional blend of luxury, comfort, and investment potential with seamless indoor-outdoor living just steps from the Pacific Ocean. The open-concept floor plan features central air conditioning, in-unit laundry, luxury finishes, and a spacious chef's kitchen with an oversized island designed for entertaining family and friends. Expansive glass doors fill the home with natural light and open to a private covered lanai with direct access to the heated swimming pool, oceanfront lawn, barbecue area, and miles of sandy beachfront beyond. The desirable ground-floor location allows you to walk directly from your lanai to the beach, creating the ultimate Maui indoor-outdoor lifestyle. Offered fully furnished and turnkey, subject to seller exclusions, the residence has an established vacation rental history and is located within one of South Maui's desirable hotel-zoned oceanfront communities, making it ideal as a personal beachfront retreat, luxury second home, or continued income-producing vacation rental. Kihei Beach Resort is a boutique oceanfront property fronting spectacular Sugar Beach, where nearly six miles of uninterrupted shoreline invite morning walks, paddleboarding, kayaking, swimming, seasonal whale watching, and unforgettable sunsets. Its convenient South Maui location provides easy access to Wailea's championship golf courses, world-class resorts, Makena's beaches, Maalaea Harbor, shopping, dining, and Kahului Airport. Whether you're seeking a legacy family beach home, a luxury island escape, or an established vacation rental investment, Kihei Beach #101 offers a rare opportunity to own an irreplaceable piece of Maui's coastline where exceptional beachfront living, proven rental performance, and long-term ownership value come together.

36 S Kihei Rd Unit 101, Kihei

Listing courtesy of Compass-W.

$475,000
1 Beds ⋅ 1 Baths ⋅ 410342 MLS ⋅ Fee Simple Tenure ⋅ Maui Vista BLDG.
Ideally positioned in one of the most desirable locations within Maui Vista, Unit 2215 is nestled in the center of Building 2, offering a peaceful setting away from the road noise experienced by some units in Building 1. This beautifully remodeled 1bd, 1bth condo features an open-concept kitchen with an expansive countertop and bar area, providing ample space for cooking, dining, and entertaining.The private lanai offers charming peekaboo ocean and mountain views, creating the perfect setting to relax and enjoy Maui's refreshing trade winds. Conveniently located in the heart of Kihei, Maui Vista sits directly across from the golden sands of Charley Young Beach and Kamaole I Beach Park, two of South Maui's most popular beach destinations. The complex also boasts three swimming pools, six tennis courts, and meticulously maintained tropical landscaping, making Maui Vista one of Kihei's most sought-after condominium communities. Don't miss this exceptional opportunity to own a beautifully updated island retreat in one of Kihei's premier locations. Contact your Realtor today to schedule a private showing!

2191 S Kihei Rd Unit 2215, Kihei

Listing courtesy of Hawaii Life (W).

$1,050,000
2 Beds ⋅ 2 Baths ⋅ 410215 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Perched at the top of Maui Kamaole affords this condo a very nice ocean view. Situated near the tropical pool, but facing away from it makes this a very quiet location. Stainless appliances, nicely furnished, new sliding glass door in the main floor bedroom and that lanai was waterproofed and retiled. A short distance to the tennis courts. Make this your Maui home today. Call your favorite REALTOR® to schedule a private showing.

2777 S Kihei Rd Unit L204, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$555,000
2 Beds ⋅ 2 Baths ⋅ 409814 MLS ⋅ Fee Simple Tenure ⋅ Mana Kai BLDG.
Own winter on Maui — for a fraction of the full-ownership price. See also MLS #409813. This beautifully renovated, fully furnished 2-bedroom, 2-bath beachfront condominium at Mana Kai Maui is offering a deeded 1/4 fractional ownership interest (maintaining compliance with HRS 514E), giving you three months (91 days spanning 1/31 to 3/31, and 7/1 to 7/31) of high-season and summer use in one of South Maui’s most treasured oceanfront settings. This is an incredible opportunity to enjoy prime beachfront ownership on coveted Keawakapu Beach for a fraction of the cost. This desirable end unit offers added privacy and quiet, positioned away from the pool activity and exterior walkway traffic. Unlike many non-end units in the building, the walkway does not pass directly in front of the guest bedroom window, creating a more comfortable and private guest suite experience. Set directly on Keawakapu Beach — one of Maui’s finest beaches for swimming, snorkeling, diving, sunbathing, stand-up paddling, kayaking, and sunset walks — Mana Kai Maui delivers the beachfront lifestyle buyers dream about. The property features a beachfront pool, front desk and lobby, ocean activities center, general store/deli, and convenient resort-style amenities. Offered with favorable Seller Financing, this is a rare and affordable way to secure Maui beachfront living in one of the island’s most beloved locations.

2960 S Kihei Rd Rd Unit 215, Kihei

Listing courtesy of McEntire Realty.

$438,000
2 Beds ⋅ 2 Baths ⋅ 409813 MLS ⋅ Fee Simple Tenure ⋅ Mana Kai BLDG.
Own winter on Maui — for a fraction of the full-ownership price. See also MLS #409814. This beautifully renovated, fully furnished 2-bedroom, 2-bath beachfront condominium at Mana Kai Maui is offering a deeded 1/6 fractional ownership interest (maintaining compliance with HRS 514E), giving you two continuous months (61 days spanning 12/1 to 1/31) of high-season use in one of South Maui’s most treasured oceanfront settings. This is an incredible opportunity to enjoy prime beachfront ownership on coveted Keawakapu Beach for a fraction of the cost. This desirable end unit offers added privacy and quiet, positioned away from the pool activity and exterior walkway traffic. Unlike many non-end units in the building, the walkway does not pass directly in front of the guest bedroom window, creating a more comfortable and private guest suite experience. Set directly on Keawakapu Beach — one of Maui’s finest beaches for swimming, snorkeling, diving, sunbathing, stand-up paddling, kayaking, and sunset walks — Mana Kai Maui delivers the beachfront lifestyle buyers dream about. The property features a beachfront pool, front desk and lobby, ocean activities center, general store/deli, and convenient resort-style amenities. Offered with favorable Seller Financing, this is a rare and affordable way to secure Maui beachfront living in one of the island’s most beloved locations.

2960 S Kihei Rd Rd Unit 215, Kihei

Listing courtesy of McEntire Realty.

$949,000
2 Beds ⋅ 2 Baths ⋅ 409770 MLS ⋅ Fee Simple Tenure ⋅ Maui Kamaole BLDG.
Discover Your Dream Getaway: Unit D208 at Maui Kamaole Nestled within the enchanting landscapes of Kihei, Unit D208 at Maui Kamaole offers an unrivaled blend of comfort, style, and convenience, setting the stage for unforgettable memories in the heart of South Maui. This meticulously renovated condo, set against the backdrop of 23 acres of lush tropical gardens, is not just a residence—it's a gateway to the lifestyle of your dreams. Elegance Meets Comfort Upon entering this exquisite unit, you'll be greeted by the warmth and beauty of bamboo cabinets and granite countertops, harmoniously complementing the cork flooring that extends from the front hallway to the downstairs bedroom. The thoughtful updates reflect a commitment to quality and aesthetics, ensuring a luxurious living experience that's both inviting and practical. The cork flooring is not only pleasing to the eye but also soft on the feet and cool to the touch, adding an extra layer of comfort to your home. A Space Designed for Living Boasting a spacious 1052 sf floor plan, Unit D208 offers ample room to relax, entertain, and enjoy the tranquility of your surroundings. With three lanais, you have private outdoor spaces to savor the peaceful garden views, away from the hustle and bustle. This unit is a true haven of serenity, offering a private setting that is a rarity in vacation rental condos. Location: The Heart of Paradise Location is paramount in real estate, and Unit D208 is ideally situated to offer the best of Maui. Just a stone's throw from Kam III Beach Park, Keawakapu Beach, and the Kihei Boat Ramp, the wonders of the island are at your doorstep. Whether it's a leisurely stroll on the beach or embarking on a water activity, everything you love about Maui is within easy reach. The proximity to Wailea Resort adds to the allure, placing world-class dining, shopping, and entertainment options just minutes away. Resort-Style Amenities Maui Kamaole is not just a place to live; it's a lifestyle. The complex features two pools and spas, tennis courts, barbecues, and spacious grass areas, all surrounded by stunning tropical landscaping. Whether you're looking for relaxation or recreation, the amenities cater to every desire. The convenience of vacation rental and long-term rental options, coupled with the complex's dedication to maintaining a high owner occupancy rate, ensures a community atmosphere that's welcoming and inclusive. Turn-Key Ready This beautifully renovated condo is offered turn-key, making it an ideal choice for those seeking a hassle-free transition to island life. With some exclusions, the unit comes ready for you to make it your own. Additionally, it's a popular rental with existing reservations, providing an excellent opportunity for investment. Your Invitation to Paradise Unit D208 at Maui Kamaole is more than a condo—it's your ticket to a life of luxury and adventure in Maui. Don't miss this opportunity to own a piece of paradise, attractively priced and perfectly positioned in South Maui. Reach out for a private tour and experience the magic of Maui Kamaole for yourself. Your dream home awaits.

2777 S Kihei Rd Unit D208, Kihei

Listing courtesy of Real Broker.

$629,000
1 Beds ⋅ 1 Baths ⋅ 409404 MLS ⋅ Fee Simple Tenure ⋅ Kauhale Makai BLDG.
Unit 505 at Kauhale Makai is a fully remodeled and furnished 1-bedroom residence currently operating as a short-term vacation rental, featuring a desirable 5th-floor orientation with ocean, pool, and courtyard views. Well-positioned within the complex for both guest experience and owner enjoyment, the unit has been consistently maintained and actively managed as a vacation rental. The interior features central air conditioning and a clean, updated design that provides comfort and consistency for both guests and owners. Sold fully furnished, it presents a compelling opportunity at a great value. Kauhale Makai is a well-known beachfront complex offering direct beach access and resort-style amenities including two pools, hot tub, sauna, BBQ areas, putting green, volleyball and bocce ball courts, all set within a lush tropical environment. Conveniently located in South Kihei, just minutes from beaches, golf, dining, and shopping. This unit is currently used as a short-term vacation rental; buyer to conduct their own due diligence regarding rental use and future regulations. Historical rental performance available upon request for qualified buyers.

938 S Kihei Rd Unit 505, Kihei

Listing courtesy of REMAX Hawaii Maui.

$550,000
2 Beds ⋅ 2 Baths ⋅ 409307 MLS ⋅ Fee Simple Tenure ⋅ Pacific Shores BLDG.
Welcome to your stunning Maui home! This fully renovated, turnkey two-bedroom, two-bath unit comes furnished, positioned in desirable South Maui. Experience island living with dining, retail, shoreline access, plus activities just steps away. Community amenities include elevator access, swimming pool, spa, along with pet-friendly policies. The unit showcases new washer and dryer, updated bathrooms with a walk-in shower, a spacious kitchen with granite countertops, stainless steel appliances, and newly remodeled flooring completed in 2024. Property shows excellent care, equipped with full-size new washer and dryer, new mailbox and two deeded parking spaces. A rare opportunity to enjoy premier coastal living—schedule a private tour with your preferred REALTOR®.

2219 S Kihei Rd Unit B314, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$345,000
2 Beds ⋅ 1 Baths ⋅ 408729 MLS ⋅ Fee Simple Tenure ⋅ Kalama Terrace BLDG.
A rare opportunity at Kalama Terrace! This spacious 2 bedroom, 1 bath end-unit offers approx. 685 sq. ft. of comfortable living with extra windows that invite natural light and cooling tradewinds. Positioned on the 2nd floor directly across from the sparkling pool and BBQ area, you'll enjoy ocean views from your private lanai and the ease of corner-unit privacy. As one of only a handful of 2-bedroom residences in the complex, this condo stands out for both size and convenience. Kalama Terrace is a boutique 61-unit community in the heart of South Kihei—just a short stroll to Charley Young Beach, Kamaole I, and the Cove, where Maui locals and visitors alike swim, surf, and watch unforgettable sunsets. Shopping, dining, and grocery stores are also nearby, making everyday living effortless. The complex has recently been refreshed with exterior painting, new gutters, and an updated pool deck and BBQ area. On-site laundry and assigned parking add to the convenience, while the monthly maintenance fee includes electricity, water, sewer, trash, propane, and grounds upkeep—keeping ownership simple and stress-free. Whether you're seeking a primary home, vacation getaway, or investment property, this South Kihei gem combines location, lifestyle, and value. Rarely available, and ready for you—schedule your showing today. Photos have been virtually staged.

35 Walaka St Unit L210, Kihei

Listing courtesy of Compass-W.

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