Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden retreat, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Ho'olei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Wailea Ekahi 28C 2 Lanai's Ground Level, Ocean View
GREAT LOCATION . WONDERFUL MORNING AND EVENING OCEAN VIEWS. LOCATED NEXT TO ONE OF THE 'QUIET' POOLS FOR AFTERNOON COOLING OFF. PLEASE NOTE :The pavilion pool will be closed Monday August 10th thru Thursday August 15, 2026 for pool resurfacing. Beach access will not be...
BEST BEACH, Kihei-Wailea, sunsets, turtles, whales, AC. APRIL & May openings
Gorgeous condo, EPIC location, A/CENJOY THE SOUND OF WAVES FROM YOUR LANAI. SEE SPECTACULAR SUNSETS, SANDY WHITE BEACH OVERLOOKING THE OCEAN AND THE ISLAND OF MOLOKINI. TROPICAL VIEWS FROM EVERY WINDOW. MOST PRIVATE UNIT IN THE COMPLEX!Hale Hui Kai is a very special,...
Wailea Luxury Beachfront Resort #904
The Palms in Wailea will allow you to 'live like the locals'. #904 is in one of the quietest corners of the community with garden, mountain and ocean views. The Palms community is an easy walk to the beach, shops, golf course and tennis courts. Walk along the ocean to...
Wailea 1 BR Condo, amazing lanai, close to everything, good pricing
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
160KReno-Stunning Palms in Wailea Condo-Beach/Golf
Brand New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa.World Class Golf+Shopping.Ground floor condo with...
Captivating Ocean View Retreat: Spacious Beauty at Wailea Elua #902
Wailea Elua #902 – Newly Remodeled Ocean View Escape with Upscale Island StyleWelcome to Wailea Elua #902, a beautifully updated second-floor, 2-bedroom, 2-bathroom condo that offers comfort, luxury, and peaceful ocean views in one of Wailea’s most sought-after...
Wailea Elua 2003 - Ground Level Gem -Oceanfront Property W/ Tropical Grounds
Wailea Elua #2003 – Elegant Ocean View Living with Ground Floor ConvenienceDiscover serene oceanview living at Wailea Elua #2003, a beautifully remodeled 1-bedroom, 2-bathroom condo with convenient ground-floor access. This upgraded unit offers comfort, privacy, and...
Wailea Oceanfront Private Home
State of Hawaii Transient Accommodations Tax License #TA-001-750-7840-01County of Maui Short-Term Rental License #Hotel-ZonedThis home defines the best of Maui with lava step access to a sandy, swimming beach on one side and a lava rock beach on the other side.This...
Outstanding Location in Maui South Kihei & Wailea
Aloha! Your dream vacation starts with our beautiful new condo, located in Southwest Maui, in the town of Kihei. The Maui Kamaole complex borders on beautiful Wailea, known for excellent restaurants and world class shopping. The lush tropical grounds spread over 23...
Wailea Sunset Condo -Wailea Ekolu Village #607- Spring & Summer Get Away Special
Welcome to our piece of paradise. Why stay in a resort hotel like the Four Seasons or the Grand Wailea when you can save 75% of the cost and not have to purchase every meal in a resort hotel? You'll have a full kitchen and a gas BBQ nearby to save on meal costs, the...
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.
ALOHA!Start your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!Immerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa, which means...
TOP Floor Corner Private Studio, Affordable Wailea, Walk to Beach
Last minute DISCOUNTED RATES We appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland management company. Enjoy sunny South Maui in our lovely studio top floor condo at the award-winning Grand Champions...
Incredibly Large Polynesian Style Villa in Wailea
Spend your vacation in this villa like Polynesian style vacation rental located at the beautiful Palms at Wailea Resort on the Maui's prestigious southern coast. The central air conditioned 1,515 Sq Ft spacious two bedroom, two and a half bath unit is the dream Hawaii...
This Wailea Ekolu retreat goes hand in hand with your Maui experience. Here you will find a clean, open, beautiful condominium, with an amazing ocean view from everywhere within the condo. This is an ideal retreat, in a perfect setting that's a fabulous value.Wailea...
Wailea Elua Village 2401 - 1 Bedroom Ocean View Condo
Completely renovated in 2019, Wailea Elua 2401 is a stunning vacation condo that features a large private wrap-around lanai with breathtaking ocean views. This beautifully designed rental offers a serene indoor/outdoor living space, perfect for enjoying Maui\'s...
Wailea Ekahi 17B - Professionally Managed
Welcome to Wailea Ekahi 17B, a one-bedroom residence in beautiful Wailea! This vacation rental offers a spacious and comfortable living space, perfect for couples or small families looking for a relaxing getaway. Step onto the large lanai with spectacular garden views...
Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142
Wailea Grand Champions #142- Garden View Comfort in the Heart of WaileaWelcome to Wailea Grand Champions #142, a beautifully maintained one-bedroom, two-bathroom villa set among lush tropical gardens and offering a peaceful retreat in one of Maui’s most sought-after...
Wailea Ekolu 403, Prime Location, Stunning Ocean Views, Spacious Lanai, Split AC
Welcome to Wailea Ekolu 403, a stunning Maui vacation rental offering breathtaking ocean views, luxurious comfort, and a prime location in the heart of Wailea. This spacious two-bedroom, two-bathroom condo sits on the lush fairways of the Wailea Blue Golf Course and...
NEW - Wailea Getaway - steps to great pool & beach
Summary:Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything!Situated above what is widely...
Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!
* * * * The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 other pools on property will remain open during this time. * * * * Escape to paradise in this luxurious 1-bedroom, 2-bath condo located in the heart of...
Newly remodeled 2-bedroom! Palms at Wailea 2303
Experience paradise in this newly remodeled 2-bedroom, 2-bathroom condo at Palms at Wailea, 2303. Nestled in a private corner of the property, this tropical oasis offers stunning sunset views, lush surroundings, and one of the largest floor plans that Palms at Wailea...
Prime Wailea Location! Wailea Ekahi 37E
Discover Hawaiian paradise at this beautifully decorated 1 bedroom, 2 bath premium condo in the oceanfront Ekahi Village resort. Highlights include: • Spacious primary suite with king bed • Living area with sleeper sofa • Split AC • Fully-equipped kitchen • Dining area...
Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea Beaches
Come experience this recently renovated gem located in the highly desired Wailea Ekolu. Expansive panoramic ocean views, natural lighting, gorgeous art, stylish furniture, and a spacious lanai are just a few of the highlights of this beautiful space. This unit has been...
Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!
E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our comfortable lanai seating you have a full 180 degree view of the islands of Molokini, Kahoolawe, Lanai, and the West Maui Mountains while enjoying your...
Palms at Wailea 1201! Perfect Location in Wailea!
Palms at Wailea 1201! Perfect location in Wailea! This 2-bed/2-bath condo offers the perfect getaway for families or couples traveling together. Enjoy lounging or dining al fresco on your private lanai! Complete with seating for six. The floor to ceiling sliding glass...
Palms at Wailea 705 - Luxury Renovation, Prime Location, Close to Shops, Full AC
* * * * The Palms at Wailea Pool Area will be Closed for Annual Maintenance Tuesday, Sept,. 15th through Friday, Sept,.18th 2026. The Pool Area Will Reopen Saturday September 19th with Regular Hours. * * * * The Palms at Wailea 705, a 2 bedroom, 2 bath ground level...
Spectacular Oceanfront Views with Split AC -Wailea
Kihei Surfside #507 features Incredible views from the lanai, kitchen, dining, and living areas. Completely renovated featuring porcelain tile flooring, custom cabinetry, granite countertops, and a fully equipped kitchen with stainless steel appliances. Bath has a...
Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!
* * * * The Palms at Wailea Pool Area will be Closed for Annual Maintenance Tuesday, Sept,. 15th through Friday, Sept,.18th 2026. The Pool Area Will Reopen Saturday September 19th with Regular Hours. * * * * Welcome to Palms at Wailea 703, your luxurious oasis in the...
Tropical garden view Wailea condo
Grand Champions 8 is a 2 bedroom, 2 bathroom condo featuring amenities such as a private lanai, air-conditioning and a washer/dryer. Located on the 3rd floor, this condo can comfortably accommodate up to 6 guests with a King-size bed in the master bedroom, a Queen-size...
Spacious Condo Near Kihei and Wailea Beaches - Kam III and Keawakapu Beach.
Come enjoy this tranquil unit with modern updated furnishings and two great lanais. Unit 59 has 2 bedrooms and 2 bathrooms with plenty of room inside and out. Well stocked with free Wifi and guest amenities. Close to the large swimming pool, hot tub, tennis court,...
Fantastic ALL NEWLY DECORATED Wailea condo
WELCOME to The Palms at Wailea, Unit 202 - your home away from home! This unit has been completely refurbished and newly decorated. The 2nd floor location provides nice vistas and a cool breeze from the large lanai (BR has AC). The living room has a new queen size sofa...
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 Bath
Bldg. 13 - Unit #118 - wonderful upgrades in a comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled...
GC 163 Spacious Wailea 2BD w AC Pool Close to Beach
Grand Champions 163 Spacious 2Bedroom, 2Bathroom Luxurious Wailea Condo. Ideal Location to Walk to Beach, Tennis, Golf, Fine Dining, Luxury Shopping, and so much more. Professionally managed by Maui Paradise Properties. Mere minutes from the extravagance of the Wailea...
Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool
Hale Wailea 6D – Wailea Ekahi Village[TA-164-628-0704-01]Welcome to Hale Wailea 6D, an elegantly updated, spacious second-floor condo nestled within the serene and beautifully landscaped Wailea Ekahi Village. This quiet, newly listed unit offers an exceptional location...
Beautiful - Palms at Wailea 1802
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is conveniently located close to the Shops of Wailea, luxury hotels, stylish boutiques, great restaurants, tennis, the Wailea...
Wailea Hm W/ Priv. Tennis/Pickleball Court Steps from Keawakapu Beach
Enjoy Old Hawaii at its best just steps from Keawakapu Beach. A spacious and tastefully decorated home, suitable for entertaining friends in the huge great room (kitchen, living room, formal dining) which open to the huge tiled lanai where you can BBQ and dine. Relax in...
Beautiful Condo, Private Lanai, Near Wailea Beaches
Address for this Condo: Grand Champions, 155 Wailea Ike Pl #5, Kihei HI 96753***Professionally Cleaned Condo, No-contact Check-In/Check Out*** Welcome to your beautiful island getaway at the luxurious Grand Champions Unit #5. This spacious condo has an open great room...
Heart of Wailea, Remodeled Kitchen + AC! Ekahi 45A
Full remodel! New AC, appliances and furnishings! Wailea Ekahi 45A is a 1 bed, 2 bath condo conveniently located on the ground floor. It has exceptional garden views with TWO large private lanais.This unit is fully equipped with all that you will need for a great...
Wailea Beach Condo W/ Ocean Views!! NEW Rates
NEWLY REMODELED BEACH CHIC CONDO with ocean views, in the heart of Wailea. Our Wailea condo offers 2 bedrooms, and 2½ bathrooms, with over 1500 square feet of indoor living space, and two lanais boasting another 500 square feet of outdoor living space on two levels! The...
Spacious Bright and Airy! Ground floor! Palms at Wailea 609
Luxury awaits at this beautifully decorated Palms at Wailea condo. With an open and inviting floor plan, there is plenty of room to spread out after a day of enjoying all that Maui has to offer. The private ground floor location makes this the perfect getaway.Maui's...
Wailea Ekahi Village 27C -- Huge 2 Floor Townhouse with Spectacular Ocean Views!
*****UPDATE: New, mini-split air conditioning system installed in August, 2025*****Ekahi Village 27C is a beautifully-decorated, updated and meticulously-maintained one bedroom, one-and-a-half bathroom condo in South Maui's prestigious Wailea resorts. The condo features...
Palms At Wailea 2002- RARE FIND - Multi Level townhouse in Wailea!
This 3 bedroom 3 bath multi level condominium apartment is like a private home! From the entry you can step up to the open living area with a ocean view lanai. The spacious living area can easily accommodate a family get together with the entertainment area and...
Wailea Grand Champions 168 - Complete Remodel - Amazing Golf Course/Ocean Views
Hawaii Tax ID: TA-144-497-4592-01COMPLETELY REMODELED - GOLF COURSE & OCEAN VIEWSGrand Champions #168 is a impeccably kept one-bedroom two-bath luxury villa with amazing golf course and limited ocean views. The unit is located on the 7th fairway of the the Wailea Blue...
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai
View! View! View! Imagine sipping gourmet coffee while enjoying the stunning ocean views and listening to the birds chirping! Imagine waking up to the mesmerizing sight of the ocean from the comfort of your bed! Imagine a sunset dinner on the lanai or taking a nap on...
Wailea Elua Village Fresh and Contemporary 2Bdr+2 Bath Oceanview Condominium
6th night free! discounts applied when booked. offer good until Dec 15th 2025.New, New, New! New paint, carpet, appliances, furniture, TV's, linens, and more to come in 2025! Top Floor Elua Village vacation home with big ocean views from the lanai, living room, and...
The Sweet Spot - Wailea Elua 3-Bdr/3-Bath Beachfront Paradise Townhouse #1004
New, New, New. Major upgrades! New floors, lighting, furniture, beds, appliances, paint, lanai furniture and artwork. Check out the new photos.This is the one, the best location at Elua. Beachfront 3 BD+3 BA private townhouse with a courtyard and a private beach lanai....
Fantastic Wailea Ekahi Beachfront Condo 45F
Welcome to my sunny Wailea Paradise! This refreshed and tastefully decorated second-floor condo (Unit 45F) has fantastic ocean and garden views and is the perfect spot for a romantic getaway or family vacation. Keawakapu Beach is just a short walk away through...
Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
Polo #406 is a beautiful, comfortable unit overlooking the ocean. It offers breathtaking views of Molokini, West Maui, Kahoolawe, and Lanai. The unobstructed sunsets are absolutely stunning!While staying at the Polo Beach Club, guests are steps away from a private,...
Wailea Ekahi 31B, 1 BR/2BA, Lower Greenbelt, Ocean View
Please read under Rules & policies-Rental Agreement the new COVID-19 Rules & Guidelines- and the Waiver of Liability Agreement that must be signed upon arrival.Welcome to our remodeled and reconfigured ground level 1 bedroom, 2 full bathrooms luxury condominium...
Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
Hawaii Tax ID: TA-144-497-4592-01 FRONT-ROW UNIT - STUNNING OCEAN & GOLF COURSE VIEWSWailea Ekolu #304 is a luxurious condominium situated at the front row of Ekolu on the 15th hole of the Wailea Blue Course with panoramic views of Molokini and Kahoolawe islands. Every...