Kaanapali Homes with Short Term Rental Allowed

Kaanapali Homes with Short Term Rental Allowed

Welcome to Kaanapali, a stunning coastal gem nestled in the heart of Lahaina, Maui, Hawaii. Renowned for its breathtaking beaches, clear azure waters, and lush tropical landscapes, Kaanapali is a paradise that offers an enviable lifestyle and a vibrant community atmosphere. As one of Maui's most sought-after destinations, this neighborhood seamlessly blends relaxation with adventure, making it perfect for both residents and visitors alike.

Kaanapali boasts a rich history as Hawaii's first planned resort community, and today, it continues to be a hub for luxury living. The area is home to a variety of upscale condos, charming beachfront homes, and exquisite villas, many of which are designed to take full advantage of the stunning ocean views. One of the standout features of Kaanapali is its allowance for short-term rentals, providing homeowners with the opportunity to generate income while enjoying the beauty of island living. This flexibility makes Kaanapali an attractive option for investors and those looking to experience the best of both worlds.

The neighborhood is also famous for its world-class amenities, including the iconic Kaanapali Beach, award-winning golf courses, and an array of shopping and dining options at Whalers Village. For outdoor enthusiasts, the nearby hiking trails and snorkeling spots offer endless opportunities for exploration and adventure.

With its perfect blend of natural beauty, luxury living, and a welcoming community, Kaanapali is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting paradise today!

Newest Kaanapali Homes with Short Term Rental Allowed

2481 Kaanapali Pkwy Unit 757, Lahaina
$1,549,999
1 Beds ⋅ 2 Baths ⋅ 411116 MLS ⋅ Fee Simple Tenure ⋅ Whaler Ii BLDG.
Ocean views, refined finishes, and a premier location come together in Whaler at Ka'anapali Beach 757. One back from oceanfront, this seventh-floor, one-bedroom, two-bath residence offers spacious interior living and a private lanai overlooking the Pacific and the island of Lanai. From morning coffee to leisurely evenings outdoors, the setting invites you to settle into Maui living. Remodeled in 2019 and enjoyed as a private residence, this pristinely maintained home features Italian quartz countertops, wood-grain Italian tile flooring, and custom cabinetry with soft-close drawers. Sub-Zero refrigeration, a Bosch dishwasher, and GE Profile appliances compliment the kitchen, while an oyster shell chandelier adds a coastal accent to the dining area. Updated sliding glass doors and custom-fit window coverings open to elegant decor and tasteful furnishings to complete the thoughtfully finished interior. In addition to being offered fully furnished, two full bathrooms, a well-appointed walk-in closet, additional storage and a Bosch laundry systems further enhance the conveniences of modern beachfront living. Positioned directly along Ka'anapali Beach, The Whaler at Ka'anapali places beachfront dining, Whalers Village shopping, championship golf, and ocean activities within easy reach. Resort amenities include an oceanfront swimming pool, fitness center, tennis and pickleball courts, barbecue areas, and beautifully manicured tropical grounds. Hotel-zoned and allowing short term rentals, Whaler 757 offers the flexibility to enjoy as a full-time residence, a personal Maui retreat, or investment property. Contact your favorite Realtor to schedule a private showing today.

2481 Kaanapali Pkwy Unit 757, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

2481 Kaanapali Pkwy Unit 461 U, Lahaina
$24,700
1 Baths ⋅ 411111 MLS ⋅ Fee Simple Tenure ⋅ Whaler Ii BLDG.
Whaler Time Interval 461 U is a studio suite with 1 bathroom located on the south side of Tower II. Enjoy the view of Lanai and the majestic Pacific Ocean. The condo is tastefully appointed with tile flooring, hardwood cabinetry, granite counter tops, and stainless steel appliances. The occupancy dates are September 30 to October 14 annually. The annual maintenance fees offer ease of payment with a portion billed in February and the balance due in the late summer/early fall. Fees include property taxes, grounds, building and unit maintenance, reserve fund, and housekeeping. The Whaler on Kaanapali Beach boasts amenities that include an ocean view pool along the famed Kaanapali Beach walk, state of the art workout facility, underground parking, tennis courts, and a business center. Beachside BBQs, on-site concierge services, and beach activity kiosk are some of the highlights offered on property. Enjoy the lush courtyard featuring tropical landscaping and a Koi fish pond. Situated in the heart of Kaanapali Beach, The Whaler is a short distance away from famed Black Rock and world class shopping and dining, as well as championship golf courses. The Whaler is zoned hotel.

2481 Kaanapali Pkwy Unit 461 U, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

150 Puukolii Rd Unit 52, Lahaina
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 411099 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Plantation BLDG.
Multi-generational enjoyment of this exceptional location, purchased specifically from the developer in 1970. The recent upgrades made in July 2026, include 3 new Split System A/C’s, kitchen and rear bedroom windows. The appliances were purchased within the past few years. It’s tiled throughout, has renovated baths with custom cabinets, & glass enclosed showers. an ample custom closet in the Main Suite, topped with a new sectional sofa. If you wish to purchase a beautifully upgraded, Ground Floor, Corner Unit, look no further. The location of this family cherished second home, is unparalleled, and includes drop- dead gorgeous views of the crystal-clear Pacific Ocean, featuring the Friendly Isle of Molokai as a backdrop. Your views are established, as the pool and tennis courts are below the front of the unit, allowing for the dramatic wide ocean vistas!! The family has owned this property since the 70’s, and renovated it as a private second home for themselves. The improvements are superb, and include an Open Floor Plan, with the kitchen, sharing the spectacular ocean views with the Great Room, and Main Suite. The second bedroom also is an on suite with very private, and quiet location in the rear of the apartment. The unit is being sold furnished, and turn key. The Kaanapali Plantation is located on the world famous Royal Kaanapali Golf Course. 10 Acres are graced with mature tropical trees, flowers, and plantings. Also included is a swimming pool, a cabana, tennis court, and shuffle board. There are 62 units, consisting of 1 bedroom 2 baths, 2 bedroom 2 baths, and 3 bedroom 2.5 baths. Another tropical touch, is that the buildings are 2 stories, so the views are optimized, while keeping a low density highly desirable place to call home! The Aluminum Roof has been installed, which is a plus for insurance purposes. This fantastic piece of Paradise is precious, as it makes you feel as if you’re in Plantation Days on Maui. This unit is in an active Vacation Rental Program, and we might be able to see if the guests would allow us to view the unit. Otherwise, it will only be available to show between check-ins.

150 Puukolii Rd Unit 52, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

130 Kai Malina Pkwy Unit 113, Lahaina
$2,100,000
2 Beds ⋅ 2 Baths ⋅ 411080 MLS ⋅ Fee Simple Tenure ⋅ Honua Kai - Konea BLDG.
Experience effortless indoor-outdoor living at Konea 113, an exceptional ground-floor residence featuring one of Honua Kai’s premier two-bedroom floor plans. With 1,325 square feet of interior living space and an expansive L-shaped lanai, this beautifully appointed two-bedroom, two-bath residence offers a rare combination of space, privacy, and convenience. One of Konea 113’s most desirable features is its direct access to the resort grounds and conveniences to the pools, gym, BBQ areas, courtyard, beach, and oceanfront path—all just moments from your door, without navigating elevators or long interior hallways. Expansive sliding glass doors connect the interior to the lanai, creating an inviting extension of the living and dining areas. Inside, the residence features a well-appointed gourmet kitchen with Bosch stainless-steel appliances and granite countertops, generous bedroom accommodations, central air conditioning, in-residence laundry, and spa-inspired bathrooms, including a soaking tub in the primary suite. Set on 38 beachfront acres along Kaanapali’s North Beach, Honua Kai delivers a true resort lifestyle with multiple pools, waterslide, hot tubs, fitness center, spa, general store, BBQ areas, and the popular Duke’s Beach House overlooking the ocean. The beachfront walking path connects you to the surrounding Kaanapali coastline and nearby resort amenities. Hotel-zoned and ideally positioned within the Konea Tower, Konea 113 combines the space of a residence with the amenities of a luxury resort and the rare convenience of ground-floor Maui living, all just moments from the beach.

130 Kai Malina Pkwy Unit 113, Lahaina

Listing courtesy of Living Maui Real Estate LLC.

130 Kai Malina Pkwy Unit 222, Lahaina
$995,000
1 Beds ⋅ 1 Baths ⋅ 411079 MLS ⋅ Fee Simple Tenure ⋅ Honua Kai - Konea BLDG.
Experience the beauty of indoor-outdoor Maui living at Konea 222, a second-floor one-bedroom residence distinguished by the largest private lanai in its class and expansive views of the West Maui Mountains. The oversized lanai creates an exceptional outdoor living space—perfect for morning coffee as the sun rises over the mountains, dining outdoors, reading in the tradewinds, or simply relaxing in the privacy of your own Maui retreat. Expansive folding glass doors open the residence to the lanai, seamlessly connecting the interior living space with the outdoors and allowing the mountain scenery and island breezes to become part of the experience. Inside, the residence offers a comfortable and thoughtfully designed floor plan with a gourmet kitchen featuring Bosch stainless-steel appliances and granite countertops, central air conditioning, in-residence laundry, spacious sleeping quarters, and a spa-inspired bathroom with a soaking tub. Set on 38 beachfront acres along Kaaanapali’s North Beach, Honua Kai offers an impressive collection of resort amenities, including multiple swimming pools, waterslide, hot tubs, fitness center, spa, general store, BBQ areas, and the popular Duke’s Beach House overlooking the ocean. Just beyond the resort, the beachfront walking path provides convenient access to the surrounding Kaaanapali coastline, beaches, and neighboring resort amenities. Hotel-zoned and ideally positioned within the Konea Tower, Konea 222 combines an exceptional oversized lanai, beautiful West Maui Mountain views, and the amenities of a premier beachfront resort—creating an inviting Maui retreat for owners and guests alike.

130 Kai Malina Pkwy Unit 222, Lahaina

Listing courtesy of Living Maui Real Estate LLC.

2661 Kekaa Dr Unit H205, Lahaina
$598,000
1 Beds ⋅ 1 Baths ⋅ 411023 MLS ⋅ Leasehold Tenure ⋅ Maui Eldorado I BLDG.
Offering tropical resort & golf course (6th fairway of the world renowned Kaanapali Royal (North) Golf Course) views from Paradise, Maui Eldordo H205 is a phenomenally spacious, single-level 1-bedroom, 1-bathroom property graciously laid across 960 living sq. ft. YOU will spend the majority of YOUR time on YOUR 216 sq. ft. lanai experiencing the outdoor Kaanapali Resort lifestyle! Recently renovated in 2026, the property is ready for the next owners to "make it their own"! Maui Eldorado is a LEASEHOLD, low-density, low-rise 204 unit community spread across twelve 2-story buildings. Maui Eldorado is zoned A-2 Apartment. Offering large floor plans, 3 pools, tennis court, exercise room and a direct oceanfront cabana, this is the perfect resort community retreat for owner, friends and guests. Located a short walk to the best sandy beaches of West Maui (Kaanapali) as well as Whalers Village, the destination for fine dining & shopping experiences! And for those that crave a cool & competitive pickleball game, there is Ohana Pickleball! Maui Eldorado H205 is LEASEHOLD property. Your Time Is Now.

2661 Kekaa Dr Unit H205, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

2661 Kekaa Dr Unit J-211, Lahaina
$399,000
1 Baths ⋅ 410979 MLS ⋅ Leasehold Tenure ⋅ Maui Eldorado Ii BLDG.
Discover this beautifully remodeled studio unit J-211 at Maui Eldorado, offering stunning views of the golf course. This is a leasehold property in the desirable J building, you'll enjoy proximity to the beach, with a bonus access to the private beach cabana reserved only for owners and guests at Maui Eldorado. J-211 is tiled throughout with beautiful built in wood cabinets, granite counter tops, stainless steel appliances and recessed lighting. The walk in tiled shower with fixed glass is both modern and functional and the matching vanity completes the whole interior look. The nearly ten acres of lush landscaped grounds features three pools, state-of-the-art workout facility, and newly added hot tub. Quiet and tranquil yet conveniently close to shops, restaurants, and beach activities, this unit is currently part of the Outrigger rental program, blending comfort and convenience. A fantastic opportunity for those seeking a Maui retreat. Maui Eldorado is officially moving forward in Maui's council-initiated hotel rezoning process under Resolution 26-111

2661 Kekaa Dr Unit J-211, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

2481 Kaanapali Pkwy Unit 1070 J, Lahaina
$80,000
1 Beds ⋅ 2 Baths ⋅ 410975 MLS ⋅ Fee Simple Tenure ⋅ Whaler Ii BLDG.
Prime inner courtyard location with stunning views! Whaler Time Interval 1070 J is a 1 bedroom, 2 bathroom suite with views of Molokai and the tip of Black Rock from the tenth floor at The Whaler. The condo is nicely appointed with tile flooring, hardwood cabinetry, granite counter tops, and stainless steel appliances. There is a Murphy Wall Bed in the living room, which is atypical in the 1 bedroom WTIOs. The lanai provides lovely outdoor space to sip a morning coffee or an evening cocktail. The occupancy dates are May 1 to May 15 annually. The annual maintenance fees offer ease of payment with a portion billed in February and the balance due in the late summer/early fall. Fees include property taxes, grounds, building and unit maintenance, reserve fund, and housekeeping. The Whaler on Kaanapali Beach boasts amenities that include an ocean view pool along the famed Kaanapali Beach walk, state of the art workout facility, underground parking, tennis courts, and a business center. Beachside BBQs, on-site concierge services, and beach activity kiosk are some of the highlights offered on property. Enjoy the lush courtyard featuring tropical landscaping and a Koi fish pond. Situated in the heart of Kaanapali Beach, The Whaler is a short distance away from famed Black Rock and world class shopping and dining, as well as championship golf courses. The Whaler is zoned hotel.

2481 Kaanapali Pkwy Unit 1070 J, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

2481 Kaanapali Pkwy Unit 1165, Lahaina
$998,000
1 Baths ⋅ 410954 MLS ⋅ Fee Simple Tenure ⋅ Whaler Ii BLDG.
Whaler 1165- Hotel Zone!! Magnificent 11th-floor studio with exceptional ocean views with the island of Lanai in the back ground. This unit is classified as a premium unit in the Aston Rental Program. This beautifully appointed residence features a full kitchen with custom cabinetry, tiled flooring in the kitchen, entry, and bath, and a stylish open tiled shower. A spacious owner’s closet with built-in dresser provides secure, lockable storage for personal belongings. Ideally located on world-renowned Kaanapali Beach, just moments from Black Rock, enjoy seasonal whale watching from your private lanai in winter and Surfers riding the waves in the Summer. A scenic beachfront path extends approximately 1.5 miles in each direction for oceanfront strolls. Resort amenities include a beachfront pool, fitness center, tennis and pickleball courts, underground parking, concierge services, and 24-hour front desk. Adjacent to Whalers Village with premier shopping, dining, and activities. Experience the Maui lifestyle at The Whaler also known as the “Jewel of the Pacific.”

2481 Kaanapali Pkwy Unit 1165, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

50 Nohea Kai Dr Unit 1-502, Lahaina
$2,850,000
1 Beds ⋅ 2 Baths ⋅ 410945 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Alii BLDG.
A truly exceptional offering at the world-class Kaanapali Alii, Unit 1-502 is a rare, one-of-a-kind residence. This stunning 1-bedroom plus den, 2-bath condo underwent a complete full-gut renovation in 2020, with no detail overlooked. The den functions as a private second bedroom with its own bathroom, offering the comfort and versatility of a two-bedroom residence. Unit 1-502 embodies sophisticated coastal luxury, with hotel-grade furnishings and impeccable finishes throughout. Ideally positioned on the highly desirable inner courtyard with fabulous ocean views, 1-502 has never been in the rental pool since its renovation and has been only lightly used, leaving it in pristine, like-new condition. Kaanapali Alii offers exceptional resort amenities, including two pools, two hot tubs, clay tennis courts, Grill Master service, a state-of-the-art fitness center, and bellman services—all just a short stroll from the shopping and dining at Whalers Village. Truly one of the most tasteful and beautifully renovated residences at Kaanapali Alii. Maui luxury lifestyle at its best.

50 Nohea Kai Dr Unit 1-502, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

2481 Kaanapali Pkwy Unit 719 F, Lahaina
$89,000
1 Beds ⋅ 1 Baths ⋅ 410877 MLS ⋅ Fee Simple Tenure ⋅ Whaler I BLDG.
WTIO 719F - Welcome to your dream coastal retreat! This seventh floor, one-bedroom, one-bath unit offers an unparalleled living experience with breathtaking ocean views and a multitude of upscale features. Step inside to discover a beautifully updated interior blending style with functionality. The heart of the home is a modern kitchen equipped with stainless steel appliances, sleek granite countertops, and custom cabinetry, perfect for culinary adventures or entertaining guests. The spacious living area seamlessly flows out to a large lanai, where you can unwind and soak in the panoramic mountain and ocean views, creating an ideal setting for relaxation or al fresco dining. This Time Interval unit allows you 2 weeks from March 7 to March 21- Peak Whale Watching Season! every year. The Whaler on Kaanapali Beach boasts amenities that include an ocean view pool along the famed Kaanapali Beach boardwalk, sauna, newly upgraded workout facility, underground parking, two tennis courts, and a business hub center. Beachside BBQs, on-site concierge services, and beach activity kiosk are some of the highlights offered on property. Enjoy the center courtyard and tropical landscaping and Koi fish pond. Situated in the heart of Kaanapali Beach, The Whaler is a short distance away from famed Black Rock and world class shopping and dining, as well as championship golf courses.

2481 Kaanapali Pkwy Unit 719 F, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

130 Kai Malina Pkwy Unit SR836, Lahaina
$2,545,000
2 Beds ⋅ 2 Baths ⋅ 410793 MLS ⋅ Fee Simple Tenure ⋅ Honua Kai - Hoku Lani BLDG.
Back On Market! Experience the perfect blend of luxury, comfort, and investment potential at Hokulani 836, a premier 2-bedroom, 2-bath, 1,240 sq. ft. corner unit in the renowned Honua Kai Resort in Maui, Hawaii. Perched on the 8th floor, this condo features an oversized lanai offering breathtaking ocean views—stretching from the Island of Moloka'i to the majestic West Maui Mountains. The lanai is the perfect spot to savor Maui’s spectacular sunsets, watch whales, or enjoy a quiet morning coffee before starting your island adventures. Hokulani 836 blends island living with modern elegance. The primary bedroom features a king bed and ensuite bathroom with a full-size shower, tub, and dual sinks. The second bedroom is versatile, offering either a king bed or two twins, and also includes a bathroom with the same luxurious features. Upgraded ceramic tile floors throughout elevate the space, while high-end furnishings, including a memory foam sleeper sofa, provide comfort for up to six guests. A fully equipped kitchen with granite countertops and full-size appliances, in-suite laundry, and an owners’ closet make this unit as functional as it is beautiful. You’ll enjoy the convenience of self-controlled air conditioning, ensuring your comfort no matter the season. The bi-fold doors seamlessly connect the living space to the oversized lanai, creating a true indoor-outdoor experience that captures Maui’s natural charm. This unit is turnkey and rental-ready, with a proven track record of strong short-term rental income. Its prime location, luxurious features, and world-class amenities make it highly appealing to vacationers, ensuring consistent demand and revenue. Ownership at Honua Kai Resort grants access to seven swimming pools, a waterslide, a 24-hour fitness center, and on-site conveniences like Duke’s Restaurant and Whalers General Store. The beachfront boardwalk offers serene oceanfront strolls, rounding out a resort experience with everything you need for relaxation and adventure. Whether you’re seeking a profitable investment property or a personal Maui retreat, Hokulani 836 offers the best of both worlds. This is your chance to own a home away from home that also serves as a money-making asset when you’re away. Claim your piece of paradise—Hokulani 836 is waiting for you.

130 Kai Malina Pkwy Unit SR836, Lahaina

Listing courtesy of Maui Westside Properties.

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