Holiday houses in Wailea
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Wailea
Total holiday rentals
Explore 1,930 holiday rentals in Wailea
Nightly prices starting at
Wailea holiday rentals start at $113 AUD per night before taxes and fees
Verified guest reviews
Over 55,470 verified reviews to help you choose
Family-friendly holiday rentals
1,150 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 10 rentals that welcome pets
Holiday rentals with a pool
1,840 properties feature pools
Rentals with dedicated workspaces
1,130 properties have a dedicated workspace
Wi-Fi availability
1,930 of Wailea holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Wailea rentals
4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated holiday rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness and more.
Go Golfing from a Peaceful Apartment in a Beach Community
Unit #903 – Key Features Garden views, ground floor A/C (3 zones) Lanai seating Quiet Updated appliances; washer/dryer Primary: king bed Second: twins (convert to king) Sleeper sofa Kitchen TV, Wi-Fi Free U.S./Canada calls Amenities Beach chairs, umbrella, boards, cooler, towels Baby gear: Pack ’n Play Pool, hot tubs Location Wailea—near beaches, golf, shops, dining. Keawakapu Beach is a short walk. Guest Support On-island contact after booking. Parking Dedicated space + guest parking.
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Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Our condo is not suitable for children or infants.
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Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.
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Wailea Beauty - walk to the beach & shops
Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.
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Luxurious Wailea Ocean Vistas
Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.
FamilyValueSleep quality
Wailea Elua condo - Ocean Views | Gym | Pickleball
Welcome to your slice of Hawaiian paradise at Wailea Elua! Here, modern luxury meets breathtaking ocean vistas, creating a serene escape for relaxation. Imagine sipping your morning coffee as whales frolic in the distance. Whether you're strolling to nearby Wailea's shops or exploring the beaches, this stunning condo offers both adventure and tranquility. Luxe Maui Properties bring professional service and 24/7 support to your stay. Secure your unforgettable getaway today!
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*Last Minute Deal*Luxurious*2b/2b OceanView Wailea
This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!
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Wailea Hidden Gem
Aloha and welcome to The Palms at Wailea! Escape to paradise in this ground level unit, including a serene bedroom, two full bathrooms, full kitchen, living room with queen-sized easy-to-close Murphy bed, and complimentary parking space. This vacation condo is fully equipped with beach gear, in-unit laundry, free WIFI, covered patio and outdoor dining, pool accessibility and hot tub, and central location to all of Maui’s most beautiful destinations.
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Wailea Ekolu – Oceanview in the Heart of Wailea
PRICE REDUCED!! Wailea Ekolu #207 is a luxurious accommodation located in the heart of Wailea, offering breathtaking views of the Pacific Ocean. The name “Ekolu” holds significance as it means “three” in Hawaiian, representing the fact that it was the third complex built in Wailea back in 1979. The suite itself provides stunning views of the three islands: Molokini, Kaho'olawe, and Lanai, further embodying the essence of “Ekolu”.
ValueLocationParking
Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at the beautiful ocean, serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)
LocationFamilyParking
Wailea Surf Shack: Beaches, Shops & Golf!
Welcome to Wailea Surf Shack, a beautifully renovated Maui retreat in the heart of Wailea. Book with confidence knowing that we live on the island, personally manage and care for the condo, and truly treat our guests like family. We go above and beyond to make sure your stay is comfortable, relaxing, and filled with wonderful Maui memories.
LocationValueBeach
Luxurious Tropical Retreat with Oceanview
Welcome to your luxurious 1-bedroom, 1-bathroom tropical oasis in the prestigious Wailea area of Maui, where modern design meets tropical paradise. This stunning retreat offers an upscale, contemporary living experience with stunning views of the Pacific Ocean and lush, manicured gardens.
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Popular amenities for Wailea holiday rentals
Other great holiday rentals in Wailea
Wailea Ocean View Escape
LocationValueOutdoor spaces
Wailea Escape/Golf Views, Beaches & Family Comfort
LocationValueBeach
Beach Front Luxury in Makena
LocationValueComfort
Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub
FamilyLocationKitchen
Stunning Wailea 2/2, AC, Upper Fl, walk to beach
LocationValueShared spaces
Wailea Elua 2401 | Wrap-Around Lanai & Ocean View
LocationPoolBeach
Gaze out at Panoramic Ocean Views from an Airy Coastal Oasis
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Newly Renovated High-end 1 bed 2 bath Wailea Condo
LocationFamilyPool
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $528 AUD | $558 AUD | $500 AUD | $442 AUD | $401 AUD | $404 AUD | $388 AUD | $374 AUD | $359 AUD | $383 AUD | $436 AUD | $515 AUD |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Wailea-Makena?
Wailea-Makena has a variety of vacation rentals, including oceanfront homes, condos, and properties near golf courses and beaches. Many neighborhoods provide easy access to local shops, restaurants, and outdoor activities.
What are the best things to do in Wailea-Makena with kids?
Children often enjoy swimming at sandy beaches, exploring tide pools, or joining marine life tours. Interactive cultural sites and family-friendly parks around Wailea-Makena are frequently suggested for a relaxed day out.
What are some of the best things to do in Wailea-Makena?
Wailea-Makena has sandy beaches, snorkeling opportunities, and scenic coastal walks. Visitors often explore local parks, enjoy golf courses, or join guided tours highlighting marine life and Hawaiian heritage.
How is the weather in Wailea-Makena?
Wailea-Makena has mild weather throughout the year, with winter temperatures averaging 53–68°F (12–20°C) and summer months reaching 59–76°F (15–24°C). Rain is more common in winter, while summers tend to be sunny and dry.
When is the best time to visit Wailea-Makena?
Late spring and summer are frequently suggested for warmer days near 75°F (24°C) and lower rainfall, making beach and outdoor activities popular. Winter, around 68°F (20°C), is also lively with more visitors, and brings occasional rain alongside mild temperatures.
What are the best places to visit in Wailea-Makena?
Visitors often explore sandy beaches, local parks, and scenic coastal paths in Wailea-Makena. Marine reserves and cultural centers highlight Hawaiian heritage, nature, and community events.
What are some hiking trails in Wailea-Makena?
Visitors can explore coastal trails, gentle walking paths through local parks, or routes winding near lava fields and scenic overlooks. Some areas have accessible hikes suitable for diverse abilities and interests.
What are some family activities we can do in Wailea-Makena?
Families can explore sandy beaches, try snorkeling in clear waters, or visit local parks with picnic spots. Cultural sites, marine life tours, and gentle hiking paths around the area are frequently suggested for visitors of all ages.
What are some of the best day trip ideas from Wailea-Makena?
Day trips can include exploring coastal hikes, visiting traditional markets, or discovering historic towns around the region. Nature reserves, scenic viewpoints, and cultural attractions frequently appeal to visitors seeking local experiences.
Are there any pet friendly accommodations available in Wailea-Makena?
Many vacation rentals in Wailea-Makena welcome pets, especially in neighborhoods near outdoor spaces or parks. Hosts often provide guidance on pet-friendly beaches and walking areas around town.
What are some local tips for visiting Wailea-Makena?
Respect beach etiquette, bring reef-safe sunscreen, and consider reusable shopping bags for local markets. Early mornings offer quieter outdoor experiences, and chatting with local hosts or vendors can reveal community traditions.
What is Wailea-Makena known for?
Wailea-Makena is known for its sandy beaches, distinct golf courses, and locally rooted hospitality. The area blends natural beauty, marine activities, and celebrated Hawaiian traditions throughout its neighborhoods.
What are the best hidden gems to explore in Wailea-Makena?
Wailea-Makena has secluded beaches, lesser-known lava rock pools, and small local markets. Off-the-beaten-path walking trails and traditional workshops offer quieter, locally rooted experiences.
What are the best foods to try in Wailea-Makena?
Local cuisine often features fresh seafood, poke bowls, and tropical fruits like papaya or mango. Try dishes rooted in Hawaiian traditions, including laulau, Loco Moco, or regional desserts made with coconut and taro.
What should I bring for a trip to Wailea-Makena?
Pack lightweight clothing, swimsuits, sun protection, and sturdy sandals for outdoor activities. Reusable water bottles, hats, and light rain jackets are useful for changing weather and exploring coastal or park areas.
What is the nightlife in Wailea-Makena like?
Wailea-Makena has a laid-back nightlife scene, with open-air lounges, live music at local venues, and casual beachside bars. Evening entertainment often blends local musicians, sunset views, and relaxed dining.
What are the most popular events or festivals in Wailea-Makena?
Annual events often include cultural celebrations, Hawaiian music festivals, and food gatherings during summer or late spring. Community events, arts fairs, and outrigger canoe races are frequently suggested for visitors seeking local traditions.
Are there family friendly vacation rentals in Wailea-Makena?
Wailea-Makena has a wide selection of family-friendly rentals, including spacious homes, condos with pools, and properties close to parks and beaches. Many hosts provide amenities like cribs, high chairs, and beach gear.
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- Maui Arts & Cultural Center
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- Maui Ocean Center
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