South Homes with Pool

South Homes with Pool

Welcome to the enchanting region of Kihei, nestled on the stunning shores of Maui, Hawaii. Known for its breathtaking sunsets and pristine beaches, Kihei offers a unique blend of laid-back island living and vibrant community spirit. This beautiful coastal town boasts an array of outdoor activities, from snorkeling in crystal-clear waters to hiking through lush tropical landscapes. With year-round warm weather, Kihei is a haven for those seeking a sun-soaked lifestyle.

Imagine waking up in your dream home, where the gentle sound of waves lapping at the shore becomes your daily soundtrack. In Kihei, you have the opportunity to own a home with a private pool, allowing you to soak up the sun in the comfort of your own backyard. These homes are designed for relaxation and leisure, with spacious outdoor areas perfect for entertaining friends and family or simply unwinding after a day of adventure.

Kihei's real estate market features a variety of stunning properties, ranging from charming beach cottages to luxurious oceanfront estates. Homes with pools are particularly sought after, providing a perfect oasis for cooling off on warm Hawaiian days. Many of these residences offer breathtaking views of the Pacific Ocean, lush gardens, and easy access to the area's best beaches.

Living in Kihei means embracing a lifestyle filled with outdoor fun, cultural experiences, and a strong sense of community. Whether you're looking for a permanent residence or a vacation getaway, Kihei's homes with pools offer the ideal blend of relaxation and island charm. Discover your slice of paradise in Kihei, where every day feels like a vacation!

Newest South Homes with Pool

$1,680,000
2 Beds ⋅ 2 Baths ⋅ 410361 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Discover one of Wailea's rarest offerings ; a beautifully appointed ground-floor residence that pairs effortless access with exceptional views. This stunning 2-bedroom condominium at Keala O Wailea offers a combination seldom found: the convenience of single-level living, breathtaking ocean views, and the privacy of one of the community's most desirable locations. Thoughtfully positioned in a quiet corner of the complex, this meticulously maintained home enjoys an expansive green lawn just beyond the lanai, making it an ideal retreat for pet owners and those who appreciate seamless indoor-outdoor living. The sense of privacy is remarkable, creating a peaceful sanctuary surrounded by lush tropical landscaping. Inside, every detail reflects quality and care. High-end luxury furnishings, sophisticated finishes, and several custom enhancements elevate the home well beyond the ordinary. The spacious, open-concept floor plan is filled with natural light and captures the beauty of Wailea from the main living areas, creating an inviting atmosphere for both everyday living and entertaining. Keala O Wailea is one of Wailea's premier luxury residential communities, ideally perched above the Wailea Blue Golf Course. This gated enclave offers an exceptional island lifestyle with resort-inspired amenities, including an elegant pool and spa, a beautifully appointed pavilion with an outdoor kitchen, and a spacious fitness center. Just moments away are Wailea's world-renowned beaches, championship golf courses, luxury shopping, acclaimed restaurants, scenic coastal paths, and the unparalleled natural beauty that defines South Maui. Whether you're searching for a full-time residence or an elegant island retreat, this exceptional home embodies the privacy, comfort, and refined island lifestyle that make Wailea one of Hawaii's most coveted places to call home.

67 Wailea Gateway Pl Unit 6-103, Kihei

Listing courtesy of Hawaii Life (W).

$859,000
2 Beds ⋅ 2 Baths ⋅ 410359 MLS ⋅ Fee Simple Tenure ⋅ Kai Ani Village BLDG.
Coming soon! Kai Ani Village is located in the heart of Kihei near restaurants, shopping centers, and Lipoa Street beach. This property features resort-style amenities including a saltwater infinity edge pool, cabanas, bbq areas and a spa. Unit 12-102 is a two bedroom, two bathroom condo located in a quiet location on the ground floor with 1,032 square feet of living space. This unit is equipped with split air conditioning and was refreshed in 2025 with updated ceiling fans, lighting, fresh interior paint, and laminate flooring throughout. Updated, professional photos are coming soon.

34 Hune One Ln Unit 12102, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$625,000
1 Beds ⋅ 1 Baths ⋅ 410356 MLS ⋅ Fee Simple Tenure ⋅ Kihei Alii Kai BLDG.
Kihei Ali‘i Kai C306 is a beautifully updated 1-bedroom, 1-bath condo in the heart of South Kihei, across from Kamaole Beach Park II. From your lanai, enjoy ocean and West Maui Mountain views as a backdrop for morning coffee or sunset pau hana. The interior has been tastefully remodeled with brand-new Wailea vinyl flooring, fresh paint, and brand-new stainless steel appliances, creating a clean, modern, and inviting island retreat. This well-situated complex places you just moments from all three Kamaole Beach parks, Cafe O’Lei in Rainbow Mall, nearby sandwich and coffee shops, and popular Kihei spots like Dolphin Plaza, all within an easy stroll. Kihei Ali‘i Kai offers resort-style amenities including a pool, spa/hot tub, dry sauna, tennis and pickleball courts, shuffleboard, barbecue areas, and nicely maintained grounds that invite you to linger outdoors. Located at 2387 S Kihei Rd, Unit C306, Kihei, HI 96753, this condo embodies the South Maui lifestyle with walkable access to multiple restaurants, stores, and some of the island’s most beloved beaches, making it an ideal home base for island living or a Maui getaway.

2387 S Kihei Rd Unit C306, Kihei

Listing courtesy of Hawaii Life (W).

$649,000
3 Beds ⋅ 2 Baths ⋅ 410350 MLS ⋅ Fee Simple Tenure ⋅ Villas At Kenolio I BLDG.
Welcome home to Villas at Kenolio 4A, a spacious 3-bedroom, 2-bath residence located just moments from the ocean and North Kihei’s beautiful nightly sunsets. This desirable residential community offers convenience at every turn, along with resort-style amenities rarely found in a residential complex, including an expansive swimming pool with a dedicated lap section, hot tub, fitness center, playground, and welcoming outdoor gathering areas. Unit 4A features a unique and flexible floor plan, with the third bedroom located in the upstairs loft. Create a private guest suite, comfortable home office, fitness area, or additional living space to suit your lifestyle. The home also offers two separate lanai areas, including a fully covered lanai off the kitchen and a second outdoor space near the front entrance. Stay comfortable year-round with central air conditioning, plus individual window AC units when you prefer to cool only certain areas of the home. Brand-new carpet was installed in July 2026, providing a fresh foundation for the next owner. Additional highlights include two assigned parking stalls and a pet-friendly community. Directly across the street, the newer Hilton Grand Vacations Maui Bay Villas has helped transform the surrounding area, creating an elevated resort-like atmosphere while still offering the ease and comfort of residential living. With convenient access to the ocean, beaches, shopping, dining, and everyday essentials, Villas at Kenolio 4A is an ideal home base for enjoying everything the Maui lifestyle has to offer.

40 Halili Ln Unit 4A, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$588,000
1 Beds ⋅ 1 Baths ⋅ 410347 MLS ⋅ Fee Simple Tenure ⋅ Kauhale Makai BLDG.
Welcome to Kauhale Makai #608, where spectacular ocean views and the relaxed South Maui lifestyle come together. Perched on the sixth floor, this beautifully situated single-level one-bedroom, one-bath condominium offers panaromic views of the Pacific Ocean, creating the perfect backdrop for morning coffee, seasonal whale watching, and unforgettable Maui sunsets. The thoughtfully designed floor plan maximizes natural light and captures refreshing trade winds, while the private lanai provides an ideal setting to unwind and enjoy the sights and sounds of the ocean. Whether you're seeking a full-time residence, a second home, or an investment opportunity, this condominium offers comfort, convenience and island charm. Kauhale Makai, known as "Village by the Sea," is an oceanfront community featuring lush tropical grounds, a swimming pool, hot tub, barbecue areas, tennis and pickleball courts, shuffleboard, and direct access to a beachfront park with miles of shoreline for recreation. Centrally located in North Kihei, you'll experience the beauty of Maui from your own oceanview retreat -- Kauhale Makai #608 is ready to welcome you home.

938 S Kihei Rd Unit 608, Kihei

Listing courtesy of Maui & Co Real Estate LLC.

$1,399,000
1 Beds ⋅ 2 Baths ⋅ 410343 MLS ⋅ Fee Simple Tenure ⋅ Wailea Ekahi Iii BLDG.
Experience effortless island living in this beautifully remodeled Wailea Ekahi Village condo, one of Wailea's most sought-after beachfront communities. This rare and desirable 1-bedroom, 2-bath floor plan is ideally positioned to capture ocean and garden views, with both the living room and primary bedroom opening directly onto the spacious covered lanai. A comprehensive 2025 remodel features ceramic tile flooring, solid-core doors, granite countertops, stainless-steel appliances, and quality finishes throughout. Vaulted ceilings, abundant natural light, and seamless indoor-outdoor living create an inviting island retreat. Air conditioning throughout, ample storage, and two bathrooms with walk-in showers provide everyday comfort and convenience. Offered fully furnished and turnkey, this residence is ready to enjoy from day one. Wailea Ekahi Village spans 34 acres of meticulously maintained tropical grounds with direct access to world-famous Keawakapu Beach. Residents enjoy four swimming pools, a beachfront pavilion, BBQ areas, Pickleball courts and beautifully landscaped walking paths. Wailea Ekahi is a pet-friendly community. It is also one of the select Wailea condominium complexes eligible for the highly desirable Wailea Golf Club membership. Just minutes from championship golf, The Shops at Wailea, luxury resorts, fine dining, tennis, and some of Maui's most spectacular beaches, this exceptional property is perfectly suited as a primary residence, second home, or highly desirable vacation rental.

3300 Wailea Alanui Dr Unit 40E, Kihei

Listing courtesy of Romvari Realty Ltd.

$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).

$395,000
1 Beds ⋅ 1 Baths ⋅ 410341 MLS ⋅ Fee Simple Tenure ⋅ Kihei Bay Vista BLDG.
Beautifully Updated 1BR/1BA Condo. This turnkey unit in the Kihei Bay Vista complex has been thoughtfully upgraded. The kitchen underwent a complete renovation with new cabinetry, granite countertops, a new refrigerator (2023), and new microwave (2024). Additional upgrades include a new wall-mounted AC unit (2022), new hot water heater (2023), and fresh paint throughout the entire unit (2023). Residents enjoy easy access to the beach, swimming pool, hot tub, BBQ grills, picnic pavilion, and tropical gardens. Move-in or ready for guests, D-207 offers easy South Maui living in close proximity to beaches, shopping, and dining. Beach-front pickleball courts just south of the complex. Don't miss this opportunity to add a turnkey Maui property to your portfolio! Easy access for showings, schedule your private showing today. This unit includes one deeded parking stall, and open parking is also available. Maintenance fee includes common area maintenance, pool maintenance, water, and Spectrum cable/wifi.

679 S Kihei Rd Unit D-207, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,795,000
3 Beds ⋅ 4 Baths ⋅ 410334 MLS ⋅ Fee Simple Tenure ⋅ Papali Wailea BLDG.
Where do timeless design, ultimate privacy, and panoramic ocean vistas all converge in Wailea? Welcome to Papali #17. Perfectly positioned in the community’s premier location, this exquisite residence is being offered for the first time since the original developer release. This single-level three bedroom and three-and-a-half baths provides the comfort and presence of a private home with the carefree and secure lock and leave benefits of a luxury condominium lifestyle. Sweeping ocean and outer-island views are complemented by Papali’s award winning design, contemporary architecture, and distinctive copper rooflines. Set on over ten acres of beautifully maintained tropical landscaping, Papali offers an exclusive sense of serenity with only two homes per acre providing privacy, tranquility, and a spacious sense of place just moments from Wailea’s pristine beaches, golf, dining, and shopping. Inside highlights include soaring vaulted ceilings with Alaskan Yellow Cedar beams, rich African mahogany millwork, limestone flooring, and a gourmet kitchen with premium granite surfaces. Flooded with natural light, expansive glass doors, and open generous lanai spaces for seamless indoor-outdoor living. Perfect for sunset gatherings and relaxed island evenings under the stars. A private garage, abundant storage, and dual entry points complete this rare and remarkable offering - furnished for your turn-key Maui lifestyle. Papali #17 isn’t just a home – it’s a legacy. Wailea’s most extraordinary offering.

3100 Wailea Alanui Dr Unit 17, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$725,000
2 Beds ⋅ 2 Baths ⋅ 410328 MLS ⋅ Fee Simple Tenure ⋅ Koa Kai BLDG.
Welcome to Koa Kai 6B, a beautifully updated 2-bedroom, 2-bath condo in a boutique, pet-friendly complex of just 18 units in the heart of South Kihei. Ocean views greet you through the large sliding glass doors, filling the living space with natural light and bringing in the relaxed feel of Maui living. The open kitchen features wood cabinetry, granite countertops, a tile backsplash, stainless steel appliances, recessed lighting, a built-in spice rack, and plenty of organized storage. Tile flooring runs throughout the unit, along with crown molding and updated windows. Both bathrooms have been remodeled, and the spacious primary bedroom includes a custom built-in closet system. Two split-system AC units help keep the home cool and comfortable year-round. Koa Kai also offers covered parking and a well-maintained pool area for residents to enjoy. Conveniently located near Kamaole Beach I, Charley Young Beach, and Cove Park, with favorite local restaurants, shopping, and everyday necessities close by. Koa Kai 6B offers ocean views, thoughtful updates, and a comfortable place to call home in one of South Kihei’s most convenient locations.

99 Walaka St Unit #6B, Kihei

Listing courtesy of eXp Realty.

$29,900,000
5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure
Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$12,500,000
4 Beds ⋅ 5 Baths ⋅ 407694 MLS ⋅ Fee Simple Tenure ⋅ Makena Beach Club & Residences BLDG.
Brand New Luxury Unit - Welcome to your new home, a spacious ground floor, 4-bedroom, 4.5-bathroom unit spanning 3,625 sq ft, nestled within Makena Beach Club and Residences. This unfurnished masterpiece offers a blank canvas for you to design your perfect living space. Step outside to your outdoor lanai, ideal for entertaining friends and family or simply enjoying the surroundings. Dive into relaxation in your private pool, surrounded by lush landscaping that enhances your outdoor oasis. Experience the luxury of wide living spaces that promote comfort and flow throughout the home. Enjoy captivating views of the future Beach Club and Spa, adding to the allure of your new lifestyle. Private club* amenities and the golf course are all within a short cart ride. The unit features a future assigned garage, a covered vehicle stall, and a dedicated parking and charging station for your golf cart, ensuring you have everything you need right at your fingertips. Don’t miss the opportunity to make this exquisite property your own. Your dream lifestyle awaits! Inquire separately about membership to Makena Golf and Beach Club.

5412 Makena Alanui Rd Unit 102/KV-3B, Kihei

Listing courtesy of Discovery Makena Realty LLC.

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