Kihei Vacation Rentals – Oceanfront Condos & Resorts in South Maui
Kihei is one of Maui's most beloved beach towns, offering oceanfront vacation rentals, budget condos, and family-friendly resorts just steps from golden beaches, casual cafés, and scenic coastlines. Explore one of Hawaii's sunniest regions with year-round warm weather, calm waters, and walkable charm.
Browse Kihei Vacation Rentals by condo/hotel name:
Located in South Maui, Kihei vacation rentals span everything from cozy studios to large oceanfront condos with resort amenities. Whether you're looking for a beachfront escape, family basecamp, or a long-term stay with kitchen and laundry, Kihei offers some of the best value and versatility in Maui.
Why Stay in Kihei?
Kihei's coastal strip is dotted with parks, beaches, and low-rise condo resorts. With over 6 miles of shoreline, guests enjoy easy access to Kamaole Beach Parks I, II, and III-great for snorkeling, swimming, or sunset picnics. Most rentals are walkable to local shops, food trucks, grocery stores, and oceanfront restaurants. Kihei's central location puts you within 10 minutes of Wailea's luxury resorts and a short drive to Maalaea Harbor or Upcountry Maui.
Top Kihei Condo Resorts
- Sugar Beach Resort – beachfront condos with pool, spa & direct sand access
- Hale Kai O Kihei – oceanfront with stunning sunsets & central location
- Maui Vista – affordable condos near Charley Young Beach
- Maui Kamaole – upscale units in a lush garden setting near Wailea
- Menehune Shores – oceanfront with rooftop BBQs and Indian restaurant
- Kihei Kai Nani – budget-friendly walk-up condos near Kamaole II
- Maui Banyan – popular with families, across from Kamaole II Beach
Key Features of Kihei Vacation Rentals
- Studios, 1-, 2-, and 3-bedroom condos with kitchens & lanais
- Oceanfront options with beach access and poolside views
- Walkable to beaches, restaurants, cafes & groceries
- On-site amenities: pools, BBQ areas, tennis courts, laundry
- Great for couples, families, remote workers & long-term stays
Explore the Best of Kihei and Beyond
- Snorkel at Kamaole Beach or paddleboard from Kalama Park
- Visit the Kihei 4th Friday town party for food, crafts & music
- Catch a snorkeling tour to Molokini Crater from Maalaea Harbor
- Drive south to Wailea's resorts, spas, and golf courses
- Explore Upcountry farms, Haleakala summit, and lavender fields
Whether you're planning a romantic escape, family trip, or snowbird retreat, Kihei offers the sunshine, affordability, and island charm to make your Maui vacation unforgettable. Start exploring your perfect Kihei vacation rental today!
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island Serenity
Welcome to Wailea Beach Villas Penthouse K107 - A luxurious and spacious 2-bedroom, 2-bath with a den that functions as a workspace or third bedroom offering 1,899 square feet of elegant island living.Perched directly above the upper pool, this villa enjoys lush...
Ground-Floor Gem in Wailea Ekahi Village
Discover true island elegance in this beautifully updated ground-floor residence at Wailea Ekahi Village, one of Maui’s most sought-after beachfront communities for vacation renters. Set within 34 acres of lush, low-density tropical gardens, the property offers direct...
Oceanview King Studio | Maui Banyan, Walk to Beach
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Enjoy your Maui getaway in this top-floor Maui Banyan studio featuring ocean views from your private...
Charming Beachside Garden Vistas
Summary:**Bright, modern, and spacious—**this completely remodeled one-bedroom, two-bath condo has been carefully designed to elevate every part of your Maui experience. From the moment you enter, the space radiates an inviting sense of calm and sophistication. Clean...
Walk to Beach | Pool + AC | Heart of Kihei
Welcome to your tropical retreat at Kalama Terrace in South Kihei — a bright, comfortable 1-bedroom, 1-bath condo perfectly situated for exploring Maui’s best beaches, restaurants, and activities. This clean and well-stocked unit offers the ideal mix of comfort,...
Sunset Views | Whale Watching | Resort Amenities - Wailea Point 3203
Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated community of Wailea Point. This elegant condo is perfect for those seeking privacy and a minimum stay of 30 nights, providing an ideal setting for a...
Watch the Golfers Play Through
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite property combines elegant design with modern amenities to provide a truly exceptional getaway experience. Upon arrival at Wailea Grand Champions 97,...
Recent Renovation - Close to Golf & Dining
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant reminder that you are vacatioing in paradise. This vacation rental offers a perfect blend of comfort and luxury, making it...
3BD Golf Haven - Great for Families
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom, two-bathroom condo offers views out over the Wailea Blue Golf Course as well as a partial ocean view. It\'s size and...
Golf + Partial Ocean Views - Grand Champions 73
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, and stunning views in the heart of Wailea, Maui. As you enter the villa, you\'re greeted by a bright and spacious great room, ideal for relaxation...
Golf + Partial Ocean Views - Grand Champions 71
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath condo comfortably accommodates up to six guests, providing ample room for...
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Golfer's Dream | Condo on Wailea Course
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of Wailea. This two-bedroom, two-bathroom condo features modern upgrades including granite countertops, new cabinetry, and...
Island Charm in Golf Community
Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart of Maui\'s paradise. This stunning two-bedroom, two-bathroom retreat offers an exceptional experience for discerning travelers seeking a memorable...
Large Floorplan - Great for Families | Grand Champions 159
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This ground-floor condo offers a spacious layout with three bedrooms and two bathrooms, making it ideal for families or groups...
Recently Renovated & Professionally Managed
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee boxes as golfers tackle the Wailea Golf Course. This vacation rental is ideally situated to showcase Mauiâs natural...
Spacious Condo in Heart of Wailea
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...
Golfer's Dream | Condo on Wailea Course
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience. This modern and hip condo boasts stunning golf course views and thoughtfully curated interior design elements that create...
Top Floor Wrap-Around Ocean Views - PH512
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream vacation. This 2,300-square-foot home features a wrap-around lanai, providing one of the most breathtaking views in the...
Walk to Waves, Snorkeling, Pool - Wailea Elua 910
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully remodeled condo offers a luxurious retreat a short stroll to one of the best snorkeling beaches on Maui. Located on the...
Modern Renovation with Ocean Views | Wailea Elua 905
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
Wailea Beach Villas PH502 - Professionally Managed
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor. Your private elevator...
Comfortable Design with Ocean Views
Wailea Elua 904 is a stunning vacation rental property that offers a luxurious island getaway. Nestled within the upscale Wailea resort community, this spacious three-bedroom, two-bathroom condominium provides guests with all the comforts of home combined with the...
Recently Renovated at Wailea Beach Villas
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of...
Spacious Condo - Great for Families
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you step inside this stunning, 1,700-square-foot condo, you\'re enveloped in a sense of luxury and tranquility. The...
Walk to Wailea Beach & Shops at Wailea
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kahoâolawe, Molokini and Lana\'i. From your private elevator landing, the suite opens...
Spacious Condo on Top Snorkeling Beach
Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea community on Maui\'s southern coast. This beautifully remodeled condo offers a serene retreat, accommodating up to six guests, making it ideal for families...
Panoramic Ocean Views - Wailea Beach Villas PH406
Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and an amazing ocean view....
Modern Renovation with Ocean Views
Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroom, two-bathroom beach house inspired condominium offers a spacious layout ideal for families or groups of friends seeking a luxurious getaway. With...
Bright & Colorful Ocean View Villa | Wailea Beach Villas PH402
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
3BD Wailea Villa - Great for Families | Wailea Beach Villas PH309
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private...
Ocean View Stunner - Professionally Managed - Elua 2402
Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. This elevated condo with vaulted ceilings enjoys great views out over the South Maui coastline, especially remarkable during whale season, since you...
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on...
Exceptional Design & Ocean Views
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Recently Renovated - Steps from Snorkeling
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired aesthetic, this condo blends comfort with contemporary style, making it an ideal getaway for families or groups of friends....
Wailea Villa in Top-Rated Hawaii Resort
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
Walk to Waves, Snorkeling, & Restaurants
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an ideal retreat for couples or small families, providing a perfect blend of comfort and elegance. The property is part of a...
Wailea Villa Overlooking Lagoon Pool
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great...
Floor to Ceiling Ocean Views - Wailea Elua 2006
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom, two-bath condo offers an ideal retreat for families or friends seeking a relaxing island escape. The residence boasts a...
Walk to Wailea Waves, Snorkeling, Restaurants
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in...
Wailea Elua 2004 | Hot tub | Pool | Sunset Views
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui\'s southern coastline. This one-bedroom, one-bathroom condominium offers an ideal retreat for couples or small families, featuring a spacious layout that maximizes comfort and ocean views...
Elevated Beachfront Views - Wailea Elua 1704
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests,...
Hear the Waves Crash - Oceanfront
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Penthouse Retreat | Walk to Wailea Beach
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the homeâs interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located...
Recently Renovated - Oceanfront in Wailea
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Recently Renovated & Professionally Managed Ocean View Villa
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking...
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway. Villa F201 is a decorator\'s dream,...
Conde Nast Award Winning Property - Wailea Beach Villas E202
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302
Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui\'s premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it...
Beachfront Condo with Postcard Views
Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental featuring an open floor plan showcases spectacular ocean views from the living room, dining area, and kitchen. The great room is perfect for...