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.
Beautifully Renovated Grand Champions! Ground Floor! Grand Champions 139
Incredible Renovation! Kick back and relax on your own private lanai and take in wonderful garden views, with some ocean and mountain views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious...
Golf course-front condo with outdoor pool, hot tub, central AC, & free WiFi
Wailea Grand Champions 149Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy your very own paradise on earth at this family-friendly, golf course-front condo! It's perfect for a...
Wailea Ekahi Village | 11A
Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea resort community, this spacious and elegantly-appointed condo provides the perfect balance of upscale amenities and serene tropical ambiance. As you step...
Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + dining
Grand Champions 136 is situated in a lush tropical setting. This 1 bedroom / 2 bathroom is located on the top floor with wonderful views of Haleakala. This condo is newly redesigned and furnished. It is the perfect setting for couples and small families. Its convenient...
Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ Views
Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views of lush landscapes rolling down to the ocean. This condo is within walking distance of the beach, the Wailea shops,...
Grand Champions 87 ocean-view condo with pool, hot tub & washer/dryer
Wailea Grand Champions 87Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Newly and beautifully remodeled from top to bottom, this golf-course-front condo in the heart of Wailea will...
Updated Wailea Condo in Oceanfront Complex!
Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available as the dining table for four and two seats at the bar area provide comfort and relaxation as you entertain family and...
Ocean views, pool, spa, and golf course nearby - Your Perfect Maui getaway.
Views of the ocean, a relaxing pool and spa, and a tropical landscape that is within minutes of beautiful sandy beaches make Wailea Grand Champions #122 the perfect home base for your island vacation. Abutting the fairways of the award-winning Wailea Blue Golf Course,...
Grand Champions 68! Enjoy stunning golf and ocean views from this inviting condo
Grand Champions 68! Beautiful golf and ocean views.As you enter you will be greeted by the charm of this condo! Open and inviting! Floor to ceiling sliding glass doors lead to your private lanai. Take in the tropical setting overlooking the golf course and ocean views...
Beautifully decorated! Very private! Partial Ocean View! Palms at Wailea 2202
The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the Shores of Maui. Very spacious and open, bringing the outdoors into your living room and kitchen! This unit is situated in the highly sought-after complex....
Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!
Wailea Ekahi Village - Spacious one bedroom, two bath condo with a enchanting garden view located in the Upper Village. New carpet throughout the unit. Master bedroom boast a King size bed. Plus there is a bonus sofa sleeper in living room. Full size washer/dryer, air...
Amazing! Beautifully remodeled and upgraded! Palms at Wailea 403
This cool, ground floor condominium is the most spacious 1200 sq ft two-bedroom 'C' plan, with sunken living room, brand new designer furniture, and extensive travertine and granite surfaces. Oceanic Time Warner cable, internet, phone, and Wi-Fi.Both kitchen and living...
Grand Champions 144 | Tropical Golf Resort w/ Pool
Whether you are looking for a relaxing getaway or seeking adventure of all kinds, Maui is the perfect vacation spot! Grand Champions 144 is a three bedroom, two bathroom condo that sleeps six guests. Enjoy the incredible primary bathroom, the private balcony with...
Prime Wailea Location! Split AC! Wailea Ekahi 36E
Wailea Ekahi 36B is a great ground floor location with lush garden views. This 1bedroom/2 bath condo offers the perfect Hawaiian retreat!Welcome to Ekahi 36B! This lovely condo offers everything you need for your Hawaiian Holiday! You will fall in love with this garden...
Wailea Elua Village | 1501
Wailea Elua Village 1501 is the perfect home base for exploring the sights, sounds, and tastes of Maui. This two-bedroom garden view vacation rental is a short drive to the top Wailea and Kihei beaches for snorkeling, favorite restaurants on the south-side of the...
Wailea Ekolu 106 | Serene Views + Access to Pool!
Start your morning with an open-air breakfast on the sheltered lanai, overlooking palm trees and the vibrant Pacific Ocean. Conclude your night stretched out on a spacious king-size bed, serenaded to sleep by the rhythmic sound of the waves. Throughout the day, take...
Makena Surf | E102 | Beachfront Resort
Makena Surf E102 is a prime oceanfront vacation condo that offers a perfect blend of luxury and natural beauty. This 1,510 square foot residence is centrally located within the resort, just a short stroll from the golden sands of Po'olenalena Beach. The condo features a...
Wailea Ekahi 52B | Resort Level Amenities!
With 34 acres of landscaped resort bordering one of Hawaii’s best beaches, Wailea Ekahi 52B is the ideal place to experience the very best of Hawaii. It’s affordable luxury that’s perfect for two couples wanting to share an island getaway. There’s a minimum stay...
Wailea Elua Village | 1502
Situated near the center of the resort, Wailea Elua 1502 is siutated near the putting green and central swimming pool. Just a short walk away is the oceanside Wailea Beach Walk where you can stroll along the shore for a few miles on a paved path and watch Hawaiian sea...
Lovely First Floor Townhome! A/C + W/D! Ekahi 25B
Welcome to Tutu’s House! Step into 25B and be transported back to the days as a child visiting your favorite Auntie or Tutu’s (grandma) home. Furnishings are new versions of classic Hawaiiana with bamboo chairs and bar stools and even a fun Queen Size Wall Bed that...
Wailea Ekolu Village | 1404
Wailea Ekolu 1404 is a beautifully appointed one-bedroom, two-bathroom vacation rental that offers an idyllic escape in Maui's popular town of Wailea. This elevated condo on the second floor boasts stunning ocean views and a serene ambiance.Upon entering, guests eyes...
REDECORATED! NEW OFFERING SUMMER 2025 - THE PALM COAST F202 OCEAN VIEW GRAND LUXE VILLA SLEEPS 8!
New Offering! Reservations are accepted now. An extensive redecoration is coming soon and F202 will be ready to greet guests as of October 2025.The Palm Coast F202 at Wailea Beach Villas recently joined Private Paradise Villas, and it will be fully refreshed with mostly...
WAILEA POINT Sweet 2 Bedroom/3 Bath Oceanview Condominium
Please call or email us about the dates for your visit. Free Car promotion! Want a mini-Cooper or similar ride while you're here on Maui - Ask us! New media posted! Check out the new photos and video. Make yourself home at Wailea Point Village 3003. A first-floor...
Palms at Wailea Villa 2203 Garden Deluxe 1 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- Spacious 473 square foot lanai- Bedroom with 1 king bed and master bathroom with shower- Queen sofa bed in sunken living room- 1022...
Palms at Wailea Ocean View Villas 1 Bedroom 2 Bath
Ocean View 1 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 2 bathrooms with shower/tub combo and 1 shower- 1 king bed or 1 queen bed- Queen sofa bed- 1022...
Palms at Wailea Ocean View Villas 2 Bedroom 2 Bath
Ocean View 2 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- Master bedroom with 1 king bed- Guest bedroom with 1 queen bed or 2 twin beds- Queen sofa bed in...
Palms at Wailea Villa 1805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- 473 square foot lanai- Master Bedroom with 1 king size bed and guest bedroom with Queen- Queen sofa bed in sunken living room- 1194...
Palms at Wailea Garden Deluxe Villas 1 BD 2 BA
Garden View Deluxe 1 Bedroom 2 Bath Villa- Full kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 1 king or 1 queen- Queen sofa bed- 1022 square feet / 95 square meters- Maximum 4...
Palms at Wailea Villa 301 Garden Deluxe 1 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- Spacious 473 square foot lanai- Bedroom with 1 king bed and master bathroom with shower/tub combo- Queen sofa bed in sunken living...
Palms at Wailea Garden Villas 2 Bedroom 2 Bath
Garden View 2 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- Master bedroom with 1 king or 1 queen- Guest bedroom with 1 queen or 2 twins- Queen sofa bed-...
Palms at Wailea Garden Deluxe Villas 2 BD 2 BA
Garden View Deluxe 2 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- Master bedroom with 1 king bed- Guest bedroom with 1 queen bed or 2 twin beds- Queen...
Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach
***Please note: This unit is under NEW ownership. The previous owner had a 10/10 rating with 67 reviews!LOCATION, LOCATION, LOCATION is everything at Ekahi Village! Ekahi Village is a premiere condo complex in beautiful Wailea, Maui. Unit 6E is perfectly situated within...
Palms at Wailea Villa 1210 Garden Deluxe 1 BD 2 BA
- Fully renovated 2nd floor walk-up unit - Renovated Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware - Spacious private 219 square feet lanai - Master bedroom with 1 king bed - No Sofa Sleeper - 2 fully...
Palms at Wailea Garden Villas 1 Bedroom 2 Bath
Garden View 1 Bedroom 2 Bath Villa- Full kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 1 king bed or 1 queen bed- Queen sofa bed- 1022 square feet / 95 square meters- Maximum 4...
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...
Chic Coastal Living in the Heart of Wailea
This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to Palms at Wailea 2206 | Your Perfect Hawaiian EscapeStep inside and be instantly captivated by breathtaking views that draw you out to the spacious private lanai....
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 473 square feet deck- Bedroom with 1 king- Queen sofa bed in living area- 1022 square feet / 95 square meters-...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503
Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...