Wailea/Makena Homes with Short Term Rental Allowed

Wailea/Makena Homes with Short Term Rental Allowed

Welcome to the breathtaking district of Wailea and Makena, nestled on the southern coast of Maui, Hawaii. This enchanting region is renowned for its stunning beaches, luxurious resorts, and vibrant tropical landscapes, making it a coveted destination for both residents and vacationers alike. With its pristine shores and crystal-clear waters, Wailea and Makena offer an idyllic paradise for those seeking a slice of island life.

Homeowners in this area enjoy the unique advantage of properties that allow short-term rentals, providing a fantastic opportunity for investment or personal use. Imagine owning a beautiful villa or a charming beachside cottage that not only serves as your private retreat but also generates rental income when you’re away. The demand for vacation rentals in Wailea and Makena is consistently high, thanks to the region’s world-class amenities, including championship golf courses, upscale dining, and exquisite shopping experiences.

As part of the vibrant Kihei community, residents can immerse themselves in the local culture, with farmers' markets, art galleries, and outdoor activities at their fingertips. Whether you’re exploring the scenic coastal trails, indulging in a sunset dinner at a seaside restaurant, or simply relaxing on the sandy shores, Wailea and Makena offer an unparalleled lifestyle.

With its stunning natural beauty and a community that embraces both relaxation and adventure, investing in a home in Wailea or Makena is not just a purchase; it’s a gateway to a lifestyle filled with joy, tranquility, and endless possibilities. Discover your dream home in this tropical paradise today!

Newest Wailea/Makena Homes with Short Term Rental Allowed

3200 Wailea Alanui Dr Unit 502, Kihei
$1,190,000
2 Beds ⋅ 2 Baths ⋅ 411174 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
PALMS AT WAILEA open-concept 2B|2B fully furnished condo features a private second-floor setting with an expansive double lanai surrounded by lush tropical foliage with a glimpse of the ocean; the perfect environment for Maui’s indoor-outdoor lifestyle. Filled with natural Maui light, it features beautiful tile flooring, two split-system AC systems, updated bathroom vanity, a seamless indoor-outdoor kitchen layout and a conveniently located assigned parking space. The exceptional location near Keawakapu Beach features beautifully landscaped grounds, a resort-style pool and spa nearby championship golf courses, tennis, pickleball, ocean activities, hiking, world-class resorts, fine dining and exclusive shopping at the Shops at Wailea and the Wailea Village. A rare opportunity offering an ideal blend of location, space, privacy, and value in the heart of the highly-desired Wailea Resort on Maui. Flexible options include vacation rentals, full-time residency or enjoyment as a second home.

3200 Wailea Alanui Dr Unit 502, Kihei

Listing courtesy of Compass-W.

155 Wailea Ike Pl Unit 151, Kihei
$950,000
1 Beds ⋅ 2 Baths ⋅ 411170 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Welcome to Grand Champions Unit 151, a beautifully renovated ground-floor one bedroom two bath condominium overlooking the first fairway of the Wailea Blue Golf Course. Enjoy spectacular year round Maui sunsets, tranquil golf course views, and a peekaboo ocean view from your private lanai. This tastefully updated residence features an open floor plan, stainless steel appliances and a queen Murphy bed for additional guests. This unit is being offered fully furnished and turn key, in a prime location ready for you to enjoy! Grand Champions offer two pools, spas, and BBQ areas surrounded by tropical landscaping. Ideally located in the heart of Wailea, minutes from world class beaches, golf, shopping and dining.

155 Wailea Ike Pl Unit 151, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3600 Wailea Alanui Dr Unit 207, Kihei
$2,395,000
1 Beds ⋅ 2 Baths ⋅ 411159 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua I A BLDG.
Enjoy the expansive ocean view over the tropical landscaping from the living area, large covered lanai and the primary suite of this spacious 1 BD/2BA ground floor unit. Wailea Elua 207 is a well maintained condo which is being sold tastefully furnished. Additionally, this unit has been updated with a new AC unit, hot water heater & dishwasher as well as two recently replace sliding doors & screens. As an added bonus there is a large walk-in storage area just inside the entrance. The Wailea Elua community is one of the few low-density, beachfront properties in Wailea. Enjoy the two pools, heated spa, paddle/tennis courts, fitness center pavilion, beachside BBQ area, putting green and manned & gated entry. Wailea Elua Village is situated right on world-famous, Ulua Beach and on the 1 1/2 mile Wailea beachfront boardwalk. Just a short distance to five-star hotels, fine dining, and the Shops at Wailea, Wailea Elua units are zoned Hotel Resort and allow Owners the ability to use the property for Short Term Vacation Rentals (STVR) to generate income if desired.

3600 Wailea Alanui Dr Unit 207, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

10 Wailea Ekolu Pl Unit 1403, Kihei
$975,000
1 Beds ⋅ 2 Baths ⋅ 411151 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekolu BLDG.
Enjoy the relaxed island lifestyle at Wailea Ekolu #1403, an updated, fully furnished one-bedroom, two-bathroom condo offering ocean views and convenient ground-level living with no stairs. The thoughtfully appointed interior features two split AC units, one in the living room and one in the bedroom, providing comfort throughout the year. Two separate lanais extend the living space outdoors, creating inviting spots to enjoy the tropical surroundings, morning coffee, or sunset evenings. Ideally located near one of the community pools and BBQ areas, this residence offers easy access to some of Wailea Ekolu’s most desirable amenities. Owners have the opportunity to join the Wailea Golf Club membership, adding another way to enjoy the resort lifestyle. Set within the renowned Wailea resort community, Wailea Ekolu #1403 is conveniently close to beautiful South Maui beaches, championship golf courses, upscale shopping, and a variety of restaurants. Whether you’re seeking a Maui getaway, a comfortable island retreat, or a place to enjoy the best of Wailea, this property offers an appealing combination of comfort, convenience, and location.

10 Wailea Ekolu Pl Unit 1403, Kihei

Listing courtesy of Hawaii Life (W).

3200 Wailea Alanui Dr Unit 1207, Kihei
$1,349,000
2 Beds ⋅ 2 Baths ⋅ 411145 MLS ⋅ Fee Simple Tenure ⋅ Palms At Wailea I BLDG.
Palms at Wailea #1207 offers a rare chance to own a beautifully remodeled, fee simple 2 bedroom, 2 bath residence in one of Wailea’s most coveted communities, at a price point that is increasingly hard to find for a 2BR/2BA in Wailea. With a ground level entry, there is no climbing to an upper floor; simply walk in to a bright, airy interior refreshed with a tasteful renovation beginning in 2023, featuring elegantly remodeled bathrooms, new flooring, an in-unit washer and dryer, and air conditioning for year-round comfort. Privately set along the tranquil inner greenbelt, the spacious lanai opens directly onto lush, meticulously maintained grounds, inviting you to unwind in the gentle trade winds. This intimate, Mediterranean-style community is surrounded by gardens showcasing more than a hundred varieties of palms, with a resort-style pool, hot tub, BBQ area, fitness center, and clubhouse just steps from your door. World-renowned Keawakapu Beach is a short stroll away, and the prestigious Wailea Resort places championship golf, fine dining, boutique shopping, and South Maui’s celebrated beaches at your fingertips. Fully furnished, impeccably maintained, and truly turnkey, #1207 is a private retreat to relax and experience the very best of Wailea living.

3200 Wailea Alanui Dr Unit 1207, Kihei

Listing courtesy of eXp Realty.

155 Wailea Ike Pl Unit 136, Kihei
$800,000
1 Beds ⋅ 2 Baths ⋅ 411042 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Desirable top-floor unit in Grand Champions, ideally located in Wailea. Featuring high ceilings and an inviting floor plan, this unit offers a bright and comfortable living space. Relax on the private lanai and enjoy beautiful garden and mountain views, peek-a-boo ocean views, and partial golf course views. Grand Champions offers two pools, hot tubs, and barbecue areas in a beautiful setting along the Wailea Blue Golf Course. Conveniently located near Wailea's beautiful beaches, golf courses, The Shops at Wailea, acclaimed restaurants, and the Wailea Tennis Club, this residence offers the perfect blend of comfort, convenience, and relaxed Wailea living.

155 Wailea Ike Pl Unit 136, Kihei

Listing courtesy of Hawaii 5-0 Properties, Inc..

3800 Wailea Alanui Dr Unit F-302, Kihei
$7,495,000
3 Beds ⋅ 4 Baths ⋅ 411032 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
The Spirit of Hawaii . . . . A timeless work of art blending retro charm with contemporary luxury. This extraordinary Villa brings character to a modern Island setting. The 2024 professionally decorated and renovated top-floor Villa is truly one of a kind at Wailea Beach Villas. This single-level technologically advanced smart residence is a rare expression of refined Maui living, combining sophisticated elegance with authentic Hawaiian soul. It features three spacious bedroom suites and three-and-a-half luxurious baths with automated window & lanai shades. The beautifully renovated interior is ideal for both relaxed island living and sophisticated entertaining. Designed for effortless indoor-outdoor living, the private turn-key Villa offers 3,568 sf total under roof living area and showcases breathtaking year-round ocean and sunset views. Amenities include an elevator, gated entry, manned security and private garage. A distinctive custom bar with a retro-inspired second refrigerator complements the newly renovated, fully stocked kitchen, which features refined finishes and premium Miele appliances, including a gas cooktop. Sophisticated, inviting, and unmistakably Maui, this exceptional residence captures the spirit of Hawaii in a way that is uniquely its own - a true one-of-one in the heart of the Wailea Resort. Its location is unsurpassed, situated on white sand beaches offering ocean activities, private beach lounge chairs and umbrellas along the renowned Wailea oceanfront pathway. Nearby, enjoy golf, tennis, pickleball, hiking, cycling, fine dining and the Shops at Wailea. You are invited to a private preview.

3800 Wailea Alanui Dr Unit F-302, Kihei

Listing courtesy of Compass-W.

3600 Wailea Alanui Dr Unit 2201, Kihei
$3,000,000
2 Beds ⋅ 2 Baths ⋅ 411022 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua Ii BLDG.
Aloha and Welcome to Wailea Elua, one of Wailea's top world class premier properties comfortably situated on twenty-five acres with direct beach and ocean access, which is HOTEL/RESORT ZONED allowing owners the ability to "SHORT TERM VACATION RENTAL" to generate income if so desired!! Wailea Elua also boasts as one of the lowest density real estate properties in all of Wailea and Makena at 6.1 units per acre, with 2201 situated on the southern most Elua border with privacy. This fine ground floor condominium offers easy access with complete pride of ownership as it has been meticulously maintained with an updated painted interior and tastefully tiled throughout which assists for easy maintenance and keeping it cool!! Beautiful and functional kitchen with all top of the line stainless appliances, separate dining area with a nice comfortable living area that opens up to 450 square feet of lanai + lush green area off of lanai. Wailea Elua offers all that one would expect in a world class resort, 24 hour gated with security, ocean front pavilion, world class shopping and dining at Shops at Wailea, directly between Andaz and Marriot Resorts for more dining, pickle ball, exercise room, bbq area, extra beach toy storage and much more!!! 2201 is completely furnished and turnkey with quality interior amenities to move right in!!

3600 Wailea Alanui Dr Unit 2201, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3600 Wailea Alanui Dr Unit 2109, Kihei
$3,000,000
2 Beds ⋅ 2 Baths ⋅ 411018 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua Ii BLDG.
Wailea Elua beachfront estate on the famed Ulua Beach with endless ocean vistas. Spacious, quiet and private - this upgraded Wailea Elua gem is located at the top of this luxurious and amenity-rich resort community. Wailea Elua is ideally located for fun in the sun. VIP front row seats await you at the Wailea Elua beachfront pool deck with direct access to the Wailea Oceanfront Beach Path, a private and large pavilion equipped with a lounge area, TVs, BBQ grills, a fitness center and more. Within this gated community, enjoy additional amenities such as a second pool, hot tub, tennis & pickleball courts and a putting green. Boasting nearly 1600 square feet of living space, this 2 bed/2 bath condo feels even more spacious with an open-floor plan allowing a seamless flow from inside to outside. The main lanai spans the entire frontage of the condo - from coffee time perched on the bedroom lanai to sunset hour on the large covered deck off the living room, you’ll love this tropical Maui retreat. A bonus, spacious patio off the kitchen allows for a special place under the stars to enjoy evening barbecues with friends and family. Preparing meals in the fully equipped kitchen with stainless steel appliances and oversized granite countertops makes cooking feel more like social hour. Being situated in a hotel-zoned resort, this condo currently operates as a successful short-term vacation rental and will be sold turn-key with all the necessities included - just pack your toothbrush and sunscreen! The spacious garage provides ample room for a vehicle as well as extra space for additional storage of your beach toys! Walking distance to the finest in world-class dining, shopping, golf and more.

3600 Wailea Alanui Dr Unit 2109, Kihei

Listing courtesy of Century 21 Island Homes.

10 Wailea Ekolu Pl Unit 1705, Kihei
$1,425,000
2 Beds ⋅ 2 Baths ⋅ 410957 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekolu BLDG.
Beautifully remodeled and filled with the relaxed spirit of Wailea, this ground-floor, walk-out residence at Wailea Ekolu offers ocean and sunset views from an elevated setting. Light and bright, the open floor plan flows naturally to a spacious covered lanai; an inviting place to dine, lounge, and enjoy Maui’s indoor-outdoor lifestyle. Even the remodeled kitchen enjoys an ocean view. Located off the foyer and thoughtfully separated from the main living area, the primary suite features an ocean view, a remodeled ensuite bath with a walk-in shower, and a convenient laundry closet. The second bedroom and remodeled guest bath are tucked beyond a hallway door that can be closed to create a private guest wing, complete with a mountain-facing lanai. Newly furnished and currently operating as a vacation rental, the residence has future guest reservations in place and offers the potential for a seamless, turnkey transition with experienced local management available. Wailea Ekolu’s beautifully maintained tropical grounds include two swimming pools and barbecue areas, all ideally located near Wailea’s beaches, golf, shopping, dining, and resorts. After more than 20 years of cherished memories with one family, this lovely Wailea retreat is ready to welcome its next owners, whether as a full-time residence, Maui getaway, or vacation rental.

10 Wailea Ekolu Pl Unit 1705, Kihei

Listing courtesy of (W)here Maui Takes You.

155 Wailea Ike Pl Unit 40, Kihei
$1,149,000
2 Beds ⋅ 2 Baths ⋅ 410950 MLS ⋅ Fee Simple Tenure ⋅ Grand Champions BLDG.
Grand Champions #40 is situated in the highly sought-after Wailea Golf Resort & near the Shops at Wailea & 5 luxury oceanfront Wailea Resorts. This is one of the nicest 2bd/2bth "lock off" units in the complex. It features its own private landing leading to both entry doors with 2 primary suites, spacious bathrooms & separate entrances, with a door in the middle of the unit that can be locked to separate one of the bedrooms/baths from the other & allowing 3 ways to utilize this condo. You can use one side with privacy & rent the other side, use it as two separate one-bedroom suites, or as a two-bedroom. The second suite has a mini fridge & microwave. This condo has been remodeled & decorated with finer fabrics & interior design, including new lighting, ceiling fan, décor & fresh interior paint. The private covered lanai features an ocean view looking west over the Pacific Ocean. The lanai is not connected to any other units, which is unusual in this complex. The condo is an end unit & offers a quieter living experience inside as well. The kitchen features stainless steel appliances, granite counters & travertine floors. The bathrooms are appointed with custom walk-in showers & etched glass. There are 2 pools & barbecue areas. Enjoy the white beaches, Wailea Tennis Center & Wailea Blue Golf Course.

155 Wailea Ike Pl Unit 40, Kihei

Listing courtesy of eXp Realty.

4400 Makena Rd Unit 109, Kihei
$3,595,000
2 Beds ⋅ 2 Baths ⋅ 410949 MLS ⋅ Fee Simple Tenure ⋅ Polo Beach Club BLDG.
At Polo Beach Club 109, the best part of a Maui day is how easily it unfolds. Open the doors to a generous ground-floor lanai, enjoy your morning coffee among the palms, and take in the ocean view before exploring the pool or the lovely sand at Polo Beach. This two-bedroom, two-bath Wailea residence offers 1,238 square feet of interior living space, an inviting kitchen and dining area, and a comfortable place to gather after a day outdoors. Its location within the property offers a quieter, more private feel while keeping the beach close. With no elevator ride between the lanai and the lawn, it is easy to head out for another swim, welcome grandchildren for a beach day, or make the kind of family memories that bring everyone back to Maui. Polo Beach Club puts Wailea’s coastal walk, dining, shopping, and golf within reach. Come for the setting; stay for the simple pleasure of making it your own.

4400 Makena Rd Unit 109, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

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