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.

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Maui Banyan 1BR | Across Kamaole Beach, Oceanview, Parking

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.Escape to this beautiful top-floor Maui Banyan retreat, where modern comfort meets the beauty of Maui's...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kihei, Hawaii

Oceanfront Luxury | Million-Dollar Views

Welcome to ultra-luxury at Menehune Shores — where the ocean views are so unreal, you’ll forget to leave. Perched oceanfront with unobstructed, panoramic vistas that look more like a screensaver than real life, this fully remodeled 2-bedroom, 2-bath condo is truly one...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

New Listing! Intimate, beach side studio getaway

Welcome to Kihei Akahi D601, your Maui retreat just steps from the beach! This beautiful studio-style condo offers the perfect blend of comfort, convenience, and island charm — ideal for couples or solo travelers looking to experience the best of South Maui. Located...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kihei, Hawaii

Wailea Ekahi Village 42D - 1 Bedroom Garden View Condo

"Welcome to your serene oasis at Wailea Ekahi Village 42D, a meticulously designed 1-bedroom garden view condo that promises an unforgettable stay. This charming retreat features a king-sized bed in the bedroom, ensuring a restful night's sleep, and a cozy living room...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Breathtaking Views -Remodeled Ocean Front Condo - Makena Surf Resort F-111

Makena Surf #F-111 – Oceanfront Comfort with Ground-Floor ConvenienceEnjoy luxurious oceanfront living at Makena Surf #F-111, a spacious ground-floor, 2-bedroom, 2-bathroom condo featuring beautiful ocean views and a peaceful island ambiance. With a prime location just...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Makena, Maui, Hawaii

Upgraded Unit w/ Beautiful Ocean Views -MAKENA SURF RESORT, #F-109

Makena Surf F109Welcome to Makena Surf F-109, a luxurious ground-floor condo in the exclusive Makena Surf. With its prime beachfront location in South Maui, this gated community offers natural beauty and sweeping views of Molokini, Kaho'olawe, and the Pacific...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Makena, Maui, Hawaii

Hilton Maui Bay Villa 3-Bedroom Premier Penthouse with Ocean View

This three-bedroom, three-bathroom ocean view suite offers a forward-facing ocean view balcony with seating for six, and furniture, textiles and finishes that are unique to the suite. The primary bedroom features a king-size bed, 55-inch TV and lounge chair and the...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kihei, Hawaii

Charming Studio New Mattress Kihei Bay Surf 236

Cozy Maui Studio with Pool, Hot Tub, Lanai & Near the BeachNew Mattress installed for a well rested Maui stay! Aloha and welcome to paradise! Experience the best of Maui from this charming studio retreat, ideally located just minutes from the beach. Whether you’re here...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 3
📍 Kihei, Hawaii

Island Surf 308 – Newly Updated with Ocean Views

Reviews (1)

Island Surf 308 – Newly Updated with Ocean ViewsExtend your escape with our special offer:Book 5 nights at any of these breathtaking properties and enjoy the 6th night free!Stay a Little Longer—On Us!Enjoy a complimentary late check-out and savor every last moment of...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kihei, Hawaii

New Listing! Direct Ocean Views, Private Lanai

Welcome to Maui Parkshore 310 – Your Oceanfront Paradise! Experience the best of Maui living at Maui Parkshore 310, a beautifully updated 2-bedroom, 2-bathroom oceanfront condo perfectly situated just steps from the golden sands of Kamaole Beach Park III. Located on the...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

Kihei Condo with Prime Beach Location and Ocean Views!

🌴 Your Maui dream vacation starts here - at Haleakala Shores A101, a bright and breezy 2-bed, 2-bath condo perfectly located just steps from Kamaole Beach Park III.🏖️ Wake up to ocean views, stroll across the street to swim or snorkel with sea turtles, and unwind at...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kihei, Hawaii

Ultimate Beach Retreat! 2BD Suite w/ Pool, Hot Tub

Come unwind at our spotless condo at the Maui Banyan Resort, just a few short steps from the soft, sandy beach. Enjoy peekaboo ocean views while you soak up the aloha spirit.✓ Right across the street from Kamaole Beach II✓ King bed + Queen bed + 2 pullout Queens✓ 2...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

New | Intro Pricing | Steps to Beach | KBC C109

Enjoy the perfect Maui getaway at this ocean-view condo, located directly across from Kamaole Beach Park I—one of South Maui’s most beloved beaches for swimming, snorkeling, and relaxing in the sun.This two-bedroom, two-bathroom condo is comfortably furnished in a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kihei, Hawaii

Wailea Point | 2301 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays

Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our other beautiful Wailea resort properties. The finest development in the finest neighborhood on the finest Hawaiian...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Grand Champions 52 - 2 Bedroom Garden View Condo

Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you\'ll be welcomed by a spacious, open living area, tastefully furnished for a relaxed...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Grand Champions 185 - 2 Bedroom Garden View Condo

This two-bedroom, two-bath villa at Wailea Grand Champions offers a perfect blend of contemporary style and tropical paradise. The open floor plan seamlessly connects the fully-equipped kitchen, dining area, and spacious living room, creating an inviting atmosphere for...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Grand Champions 177 - 1 Bedroom Golf Course View Condo

Welcome to Maui\'s Wailea Grand Champions, a paradise nestled in the heart of Wailea. This exquisite one-bedroom, two-bathroom vacation rental offers the perfect blend of comfort, luxury, and breathtaking views, ideal for couples or small families seeking an...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Grand Champions 140 - 2 Bedroom Garden View Condo

Reviews (1)

Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance with comfort, offering a luxurious retreat that is perfect for both relaxation and adventure. Upon entering Wailea Grand...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Grand Champions 102 - 2 Bedroom Golf Course View Condo

Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Beach Villas PH508 - 3 Bedroom Ocean View Penthouse

Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout—perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design unlike...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

Wailea Elua Village 707 - 2 Bedroom Ocean View Condo

Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll to the beachfront pavilion with swimming pool. This vacation rental in the heart of Wailea offers guests a comfortable and upgraded home which...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Beach Villas PH404 - 2 Bedroom Ocean View Penthouse

Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho\'olawe and...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Elua Village 706 - 2 Bedroom Ocean View Condo

Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the spacious and thoughtfully designed interior. The open concept living area is flooded with natural light, creating a warm...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Beach Villas PH403 - 3 Bedroom Ocean View Penthouse

Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

Wailea Elua Village 2108 - 2 Bedroom Ocean View Condo

Welcome to Wailea Elua Village #2108. This two-bedroom, two-bath residence is fully remodeled and redecorated, features an extra-large floor plan of more than 1,500 square feet, and boasts gorgeous, elevated views of the ocean, off-shore islets, and lush tropical...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Elua Village 2102 - 1 Bedroom Garden View Condo

Wailea Elua 2102 is a delightful one-bedroom with a bonus room, two bathroom second-floor condo that comfortably accommodates up to five guests. Designed with a relaxed, island-inspired style, this residence blends casual elegance with modern comfort, creating an...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 5
📍 Wailea, Hawaii

Wailea Beach Villas PH205 - 3 Bedroom Garden View Penthouse

Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

Wailea Beach Villas PH106 - 2 Bedroom Garden View Penthouse

Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Elua Village 1510 - 2 Bedroom Ocean View Condo

Wailea Elua 1510 is a charming two-bedroom, two-bathroom vacation rental located in the premier Maui vacation destination of Wailea. This upstairs condo offers stunning ocean views and is just a short stroll away from the pristine Ulua Beach, one of the favorite...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Beach Villas PH104 - 2 Bedroom Garden View Penthouse

Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Elua Village 1509 - 2 Bedroom Garden View Condo

Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destination. Enjoy easy access from this vacation condo at Wailea Elua Village to the restaurants and spas of the Wailea resorts via the picturesque Wailea...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Elua Village 1504 - 2 Bedroom Ocean View Condo

Wailea Elua Village 1504 is a luxurious vacation rental located in the picturesque Wailea area of Maui. This beautifully designed two-bedroom, two-bathroom condo will check all the boxes your are looking for in your Maui vacation rental steps from the beach. The...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Beach Villas G101 - 3 Bedroom Garden View Villa

Villa G101 is, simply stated, lovely. Swaying palms and a smiling Buddha welcome you into the golden pearl and shell inlay foyer of this beautiful three bedroom, three and a half bath luxury vacation home. 3,592 square feet provide you indoor-outdoor living in the...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

Wailea Elua Village 1202 - 1 Bedroom Ocean View Condo

Wailea Elua 1202 is a stunning vacation rental property that offers visitors a truly luxurious and unforgettable experience in the heart of Maui\'s renowned Wailea resort area. Situated just steps away from the pristine white sands and crystal-clear waters of Ulua...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village 104 - 1 Bedroom Ocean View Condo

Wailea Elua Village 104 is a stunning Wailea condominium rental that offers a truly unparalleled Hawaii vacation experience. Situated along the pristine golden sands of Ulua Beach on Maui\'s southern shore, this luxurious one-bedroom, two-bathroom condo provides guests...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekolu Village 1203 - 1 Bedroom Ocean View Condo

Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning travelers seeking the best of Wailea. This sanctuary offers a seamless indoor-outdoor living experience, allowing guests to enjoy breathtaking panoramic...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ekahi Village 6F - 1 Bedroom Garden View Condo

Wailea Ekahi Village 6F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo located within the resort community of the Wailea Ekahi Village, a low-density collection of condo clusters set across 34 acres of beautifully...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 54B - 1 Bedroom Garden View Condo

Wailea Ekahi 54B is a luxurious one-bedroom two-bathroom vacation rental offering an exceptional blend of comfort and elegance, set within the stunning Wailea Ekahi Village. This inviting ground floor condo boasts a prime location with direct access to lush, tropical...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 52D - 1 Bedroom Garden View Condo

Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 51D - Wailea Ekahi Village 51D

Wailea Ekahi Village tropical vacation condos are situated above Maui\'s beautiful Keawakapu Beach and close to all the top Wailea resort hotels. Enjoy easy access from your vacation condo at Wailea Ekahi Village to the restaurants and spas of the Grand Wailea, Four...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekahi Village 50C - 1 Bedroom Garden View Condo

Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation rental situated in the heart of Wailea. This elegant ground floor condo offers the perfect blend of modern comfort and tropical charm. From the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 49C - 1 Bedroom Ocean View Condo

Wailea Ekahi Village 49C is a charming vacation rental located in one of the most popular Wailea vacation rental communities. This one-bedroom ocean-view condo offers a perfect blend of comfort, luxury, and tropical ambiance, making it an ideal destination for travelers...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Ekahi Village 49B - 1 Bedroom Ocean View Condo

Wailea Ekahi 49B is a stunning ocean view condominium located in the heart of the renowned Wailea resort area. Nestled along the pristine white sand beaches of Keawakapu Beach, this luxurious condo complex offers sits on 34 acres of lush tropical landscaping. Spanning...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 47E - 1 Bedroom Garden View Condo

Wailea Ekahi 47E is a beautiful vacation rental nestled within the landscaped 32 acres of lush tropical gardens that make up Wailea Ekahi Village. This condo offers a precise blend of comfort and tropical elegance, making it the perfect home to relax and unwind after a...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 47D - 1 Bedroom Ocean View Condo

Wailea Ekahi 47D is a spacious and beautifully updated one-bedroom, two-bath condo located in one of Wailea’s most sought-after beachfront communities. Perched on a gentle slope, this upper-level unit offers breathtaking ocean views from the private lanai, perfect for...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 47B - 1 Bedroom Garden View Condo

Welcome to your tropical retreat at Wailea Ekahi Village 47B—an ideal vacation escape for families or a group of friends. This beautifully appointed ground-floor residence offers the perfect blend of comfort, space, and convenience. With serene garden views and easy...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Ekahi Village 26D - 1 Bedroom Garden View Condo

Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on Maui’s sunny south shore, 26D is a tranquil second-floor unit that offers the perfect blend of privacy, comfort, and...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Makena Surf B204 Beachfront Resort - 2 Bedroom Oceanfront Condo

Experience the ultimate beachfront getaway at this luxurious 2-bedroom oceanfront vacation rental at Makena Surf, located on the stunning shores of Maui. This exquisite condominium offers breathtaking views of the Pacific Ocean and the nearby islands, including Molokini...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Makena Surf A204 Beachfront Resort - 2 Bedroom Oceanfront Condo

Makena Surf A204 is a luxurious oceanfront residence offering a serene Hawaiian retreat. This spacious 1,600 square foot condo, located on the second floor, boasts breathtaking ocean views and direct access to the pristine Po\'olenalena Beach. The open-concept layout...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Luxury Oceanfront 3-bedroom Retreat with AC in the heart of Kihei

Nestled in Kihei, this delightful condo boasts 3 bedrooms including 2 king beds, 1 queen bed, and 1 bunk bed. With 3 bathrooms featuring a bathtub, shower, and jetted bathtub, guests will feel right at home. The additional living room space with 1 queen bed and 1 full...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 11
📍 Kihei, Hawaii

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