Holiday houses in Wailea
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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 $136 NZD 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 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.
Mana Kai Palms Oceanfront Condo: Keawakapu Beach
Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms
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A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views
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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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Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best PM in Maui, Tracy O'Reilly to take amazing care of you!
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MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!
This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!
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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 Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.
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*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini
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Grand Champions - King Bed - Close to Wailea Beach
We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course. Have fun with the whole family at this stylish place.
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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.)
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Maui Wailea Brand New Modern Spacious Condo
Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )
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Popular amenities for Wailea holiday rentals
Other great holiday rentals in Wailea
Beach Front Luxury in Makena
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Elua 1310 Oceanfront -Family Managed-Remodeled9/25
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Wailea Ocean View Escape
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Stunning Wailea 2/2, AC, Upper Fl, walk to beach
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Aloha Moon - The Honeymoon Hideaway
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Wailea Hidden Gem
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Beach Front Wailea, Full Ocean View A/C, ELUA102
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Wailea Escape/Golf Views, Beaches & Family Comfort
LocationFamilyLaundry
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $636 NZD | $671 NZD | $602 NZD | $532 NZD | $483 NZD | $486 NZD | $467 NZD | $450 NZD | $432 NZD | $461 NZD | $525 NZD | $620 NZD |
| 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.
Destinations to explore
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Maui Vista Condominium
- Wailea Beach
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Aston Mahana at Kaanapali
- Maui Ocean Center
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Hāmoa Beach
- Kahana Beach
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