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

$1,245,000
1 Beds ⋅ 2 Baths ⋅ 410331 MLS ⋅ Fee Simple Tenure ⋅ Mahana BLDG.
Experience the pinnacle of oceanfront living at The Mahana at Ka’anapali. The 9th floor is dreamy, with year round sunsets and fabulous ocean and two island views. Unit 915 features floor-to-ceiling glass walls that frame panoramic, unobstructed views of the Pacific and the silhouettes of Lanai and Molokai. This open-concept residence is uniquely designed, offering one of the few one-bedroom floor plans that includes TWO full bathrooms for added convenience and privacy. Sold fully furnished, the interior flows seamlessly from a modern kitchen into a primary suite where you’ll wake up to the rhythmic sight of turquoise waves. The private, spacious lanai serves as your front-row seat to the best of Maui, from watching sea turtles navigate the reef to taking in legendary year-round sunsets. On-site, enjoy a curated collection of amenities including a beachfront pool, hot tub, tennis courts, and lush tropical grounds. Whether you’re looking for a sophisticated personal getaway or a turnkey investment, this HOTEL-ZONED residence offers versatility and an unparalleled lifestyle where the ocean is truly your backyard.

110 Kaanapali Shores Pl Unit 915, Lahaina

Listing courtesy of Compass-W.

$489,000
1 Beds ⋅ 1 Baths ⋅ 410304 MLS ⋅ Leasehold Tenure ⋅ Maui Eldorado I BLDG.
Pristine, immaculate, totally turnkey, and spacious - just a few of the superlatives that come to mind when describing Maui Eldorado E102. Boasting 960 sf - this one bedroom, one bathroom condo is thoughtfully upgraded throughout and offers the serenity of a very private lanai for enjoying ocean breezes. Ownership is refreshingly simple here: the HOA fee includes ALL utilities, even electricity and central air-conditioning. This unit also includes dedicated, HOA-approved storage — an uncommon perk at the complex. Maui Eldorado offers true LOCATION, LOCATION, LOCATION on approximately 10 lush acres fronting the Royal Ka'anapali Golf Course, with three pools, underground parking, a complimentary golf-cart shuttle, a fully equipped one-site fitness center, AND the resort's popular beach cabana on Ka'anapali Beach. Whalers Village dining and shopping, tennis courts, and popular beach activities are just minutes away. Offered as 90% leasehold / 10% fee-simple — a "sandwich" ownership structure that makes this premier Ka'anapali address attainable. Opportunity is calling!

2661 Kekaa Dr Unit E102, Lahaina

Listing courtesy of Maui Luxury Real Estate LLC.

$1,095,000
2 Beds ⋅ 2 Baths ⋅ 410284 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Plantation BLDG.
Embrace island living in this beautifully renovated two-bedroom, two-bathroom ocean-view residence on the hillside of Kaanapali. Nestled within the privacy of Kaanapali Plantation, a boutique community of 62 residences spread across 10 meticulously landscaped acres, this turnkey retreat is defined by open living spaces, captivating ocean views, and a peaceful setting just moments from the best of Kaanapali. Thoughtfully reimagined in 2023, Kaanapali Plantation 43 has been refreshed from top to bottom with new appliances, windows, doors, flooring, cabinetry, bathrooms, and more. As a bright end unit sharing only one common wall neighbor, the home lives with a sense of space and privacy rarely found in condominium living. Framed by sweeping views of the Auau Channel, with Lanai and Molokai on the horizon, the spacious lanai and primary bedroom provide a front-row seat to seasonal whale watching, brilliant sunsets, and unforgettable nights beneath the stars. When you're not exploring the best of West Maui, enjoy the relaxed lifestyle offered within the community, featuring a swimming pool, tennis courts, shuffleboard, and a recreational gathering area for owners and guests alike. Just minutes from world-renowned beaches, championship golf, hiking trails, shopping, and dining, Kaanapali Plantation offers the ideal balance of peaceful seclusion and effortless access to everything the island has to offer. Whether you're searching for an exceptional island getaway, a full-time residence, or the opportunity to own in one of Maui's most sought-after locations, welcome home to Kaanapali Plantation 43. One of the sellers holds an active Hawaii real estate license.

150 Puukolii Rd Unit 43, Lahaina

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

$1,195,000
2 Beds ⋅ 2 Baths ⋅ 410237 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Royal BLDG.
Picture yourself beginning each morning with Kona coffee on your expansive private lanai, where gentle ocean breezes and panoramic Pacific views welcome you to island life at Kaanapali Royal. Beautifully remodeled, this spacious 2-bedroom, 2-bath residence offers approximately 1,580 square feet of bright, open living with white cabinetry, quartz countertops, updated bathrooms, central air conditioning, and stylish furnishings throughout. The generous 380-square-foot lanai is perfect for relaxing, entertaining, or taking in Maui’s spectacular sunsets. Nestled along the Kaanapali Kai Golf Course, Kaanapali Royal features a pool, spa, tennis courts, and lush tropical grounds, all just a 5-minute stroll from world-famous Ka'anapali Beach, Whalers Village, oceanfront dining, shopping, and snorkeling. Offered fully furnished, this is an exceptional investment opportunity, which offers the ideal blend of comfort, convenience, and the relaxed Maui lifestyle.

2560 Kekaa Dr Unit N302, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$999,999
1 Baths ⋅ 410195 MLS ⋅ Fee Simple Tenure ⋅ Whaler I BLDG.
Experience the best of Ka'anapali Beach from this beautifully positioned 11th-floor residence at The Whaler. Unit 1115 offers breathtaking panoramic views of the Pacific Ocean, the neighboring islands of Lanai and Molokai, and Maui's spectacular year-round sunsets from its spacious private lanai. Thoughtfully maintained and tastefully appointed, this turnkey condominium combines island elegance with the comfort and convenience of a premier beachfront resort. Located in the heart of world-famous Ka'anapali Resort, The Whaler places you just steps from pristine white sand beaches, championship golf courses, Whalers Village shopping and dining, and an array of ocean activities. Resort amenities include a beachfront pool and spa, tennis courts, fitness center, sauna, BBQ areas, tropical landscaped grounds, and 24-hour front desk and security. Whether you're seeking a luxury vacation retreat, a successful vacation rental investment, or both, Unit 1115 offers an exceptional opportunity to own in one of West Maui's most sought-after beachfront properties. Seller has an active Real Estate License in the State of Hawaii.

2481 Kaanapali Pkwy Unit 1115, Lahaina

Listing courtesy of Coldwell Banker Island Prop(S).

$1,200,000
2 Beds ⋅ 2 Baths ⋅ 410174 MLS ⋅ Fee Simple Tenure ⋅ International Colony Club I BLDG.
Discover Maui living at International Colony Club 20, a charming free-standing cottage on Kaanapali's hillside, close to Kahekili Beach Park (North Kaanapali Beach) for swimming and snorkeling and the Royal Kaanapali Golf Course. If you are looking for a property with character and the feel of classic Hawaii home, International Colony Club offers something truly unique in the West Maui market. Cottage 20 features vaulted ceilings, a remodeled interior and has been upgraded with a split-system AC. Includes an owned Photovoltaic Solar system with a Tesla back up battery. The spacious covered lanai is ideal for entertaining and opens to a large grassy outdoor space with a swimming pool just across the green. Fruit trees and tropical grounds add to the allure. Short-term vacation rentals are permitted, and this property is not impacted by Bill 9. Perfect vacation retreat, full time home, or part-time Maui hideaway.

2750 Kalapu Dr Unit 20, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$949,000
1 Baths ⋅ 410169 MLS ⋅ Fee Simple Tenure ⋅ Maui Kaanapali Villas BLDG.
Enjoy the Maui lifestyle at the renowned Maui Ka'anapali Villas, where timeless island charm meets modern luxury. Your investment will be working while you are away! This resort is approved to continue short term rentals and guests keep coming back for its prized location with all the amenities on Ka'anapali beach. This 5th-floor Premium ocean-view studio, door number 518, captures the ocean views and breezes. It was completely gutted and remodeled in 2023, showcasing crisp modern finishes and contemporary design. The thoughtfully updated interior offers a fresh, stylish aesthetic that enhances guest appeal and rental performance. Reservations stay very busy and reviews are amazing for this unit with strong income numbers and year-over-year growth. Maui Kaanapali Villas remains one of West Maui’s most desirable vacation destinations, prized for its prime beachfront location on North Kaanapali Beach and convenient access to world-class golf, shopping and dining at Whaler's Village, and a Tennis Ranch right next door, all connected by a 3 mile beach walk trail. Voted "America's best beach" numerous times, this complex is located on the North side of black rock with far less crowds and the same crystal clear water and fine white sand. Resort amenities include two swimming pools, hot tubs, BBQ's, a fitness center, community laundry, lush tropical grounds, beachfront access, and the popular onsite restaurant Castaway Café. Very few Maui condos have the convenience of a signature restaurant on property. Everything is right at your fingertips at the Maui Kaanapali Villas. It is also just a short drive to more of Maui's most beautiful beaches along the west Maui coast, from Kapalua to Lahaina. Whether you're expanding your portfolio, seeking a 1031 exchange opportunity, or looking for an investment property that can also serve as your personal island retreat while still generating income to help with expenses, this beautifully renovated ocean-view studio offers the rare combination of location, quality, and proven rental performance in one of Maui's most established resort communities.

45 Kai Ala Dr Unit A509, Lahaina

Listing courtesy of Compass.

$2,595,000
1 Beds ⋅ 2 Baths ⋅ 410141 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Alii BLDG.
Prime penthouse location with stunning ocean views overlooking world famous Kaanapali Beach and Black Rock. This one bedroom plus den can sleep up to 6 guests and features granite countertops, custom cabinetry, two walk in showers as well as tile flooring throughout. The amenities at the Kaanapali Alii include: two pools, two hot tubs, beachfront barbecue grills, state-of-the-art fitness center with spa services, 3 tennis courts and concierge and bell services. Kaanapali Alii is ideally located in the center of Kaanapali Beach for you to enjoy beach days, snorkeling, sailing, whale watching, 36 holes of world class golf, and shopping & dining at Whalers Village.

50 Nohea Kai Dr Unit 1-1101, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$4,850,000
2 Beds ⋅ 2 Baths ⋅ 410106 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Alii BLDG.
Penthouse offering in the highly desirable Kaanapali Alii community. Situated on the Top Floor, this 2 Bedroom 2 Bath Plus Den functions like a 3 Bedroom and is considered by many to be the most desirable floor plan at the Kaanapali Alii. The Top Floor location offers incredible Ocean views, Mountain views, Golf Course views and views of Kaanapali Beach. Enjoy the perfect Beachfront Lifestyle with everything that Kaanapali has to offer. It is just a short beachfront walk to Whalers Village for some of the Best Restaurants and Shopping that Maui has to offer. The property is in a successful rental program with strong rental income, making it a perfect fit as a turn key luxury resort rental or as a second home.

50 Nohea Kai Dr Unit 3-1104, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,100,000
2 Beds ⋅ 2 Baths ⋅ 410098 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Royal BLDG.
Ka'anapali Royal K101 enjoys what we feel is the most liveable floor plan in Ka'anapali, overlooking the golf course with the ocean in the distance. This spacious and unique ground floor 2 bedroom, 2 bath unit features a gourmet kitchen open to the generous living area, with ensuite bedrooms and laundry closet separated by the entry area. It has been tastefully remodeled, including a beautifully tiled master bath in 2022. The extra large covered lanai includes a sink and portable BBQ-perfect for entertaining, and also offering quick access to the pool area. You'll love the close proximity to world famous Ka’anapali Beach and 2 golf courses, as well as the fine dining restaurants and shops at Whalers Village. On site amenities include large storage closet next to the entry door, central AC, pool, spa, BBQ with covered outdoor dining area, and tennis courts. Though currently approved for short term rentals, this unit has been lovingly occupied by the owners. Call your favorite agent soon for a showing and recent County info regarding short term rentals.

2560 Kekaa Dr Unit K101, Lahaina

Listing courtesy of Moffett Properties LLC.

$65,000
1 Beds ⋅ 2 Baths ⋅ 410027 MLS ⋅ Fee Simple Tenure ⋅ Whaler I BLDG.
Whaler Time Interval 608S - Enjoy spectacular 6th-floor views from Tower I at The Whaler, where you look directly up the shoreline toward Black Rock and the stunning north end of Kaanapali Beach. This beautifully appointed 1-bedroom, 2-bath interval ownership offers annual usage every year from September 6th to September 20th, giving you two unforgettable weeks in one of Maui’s most desirable beachfront resorts. Inside, you’ll find a spacious and tastefully furnished residence featuring a full-size kitchen with granite countertops, stainless steel appliances, and an in-unit washer and dryer—everything needed for a comfortable and effortless island escape. The Whaler’s resort grounds are impeccably maintained and designed for relaxation, featuring a freshwater koi pond, lush tropical gardens, oceanfront swimming pool and Jacuzzi, fitness center, tennis courts, pickleball courts, and underground parking. Perfectly located in the heart of Kaanapali and adjacent to Whalers Village, you’ll enjoy easy access to over 80 shops and restaurants, plus beachfront dining, sunset strolls, happy hours, and endless days lounging by the ocean or play at one of the two resort style golf courses just behind the resort. Annual association dues are $4,566 (paid in two installments in February and August). Ownership includes the added value of no resort or parking fees for owners, making your effective stay approximately $380 per night for a luxury ocean-view one-bedroom at one of Maui’s premier beachfront destinations. Secure your place at The Whaler and create lasting Maui memories year after year.

2481 Kaanapali Pkwy Unit 608 S, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$2,275,000
2 Beds ⋅ 2 Baths ⋅ 410012 MLS ⋅ Fee Simple Tenure ⋅ Kaanapali Alii BLDG.
Enjoy beautiful mountain views and exceptional privacy from this spacious 5th-floor corner residence at the Kaanapali Alii. Located above the treetops, this two-bedroom, two-bath condominium offers approximately 1,691 square feet of interior living area plus a 116-square-foot covered lanai. Covered parking stall G15 is included, a valuable feature not available to all owners. Currently participating in the rental program, the residence may be shown between guest arrivals and departures. For buyers seeking an attractively priced opportunity within the Kaanapali Alii, this residence offers the rare combination of beautiful views, privacy, covered parking, and value. Why settle for less when you can enjoy all of these benefits in one of Maui's premier oceanfront condominium resorts?

50 Nohea Kai Dr Unit 4-505, Lahaina

Listing courtesy of Kaanapali Resort Realty LLC.

Start Your Search