Holiday rentals in Wailea

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Top-rated holiday rentals in Wailea

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern open-concept living area features a round wooden dining table in the foreground, surrounded by white chairs. In the background, a well-equipped kitchen displays sleek appliances. A cozy seating area with light-colored couches is visible, complemented by natural lighting from large sliding glass doors.
Apartment in Wailea
4.93 out of 5 average rating, 189 reviews

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 private lanai that overlooks the grass.King Master Bed with a private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel/take long tropical beach walk.BOOKINGS UP TO 365 DAY

Guest favourite
A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.
Apartment in Wailea
4.95 out of 5 average rating, 216 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

Top guest favourite
An open dining area features a round table made of natural wood, surrounded by woven chairs. A well-equipped kitchen with stainless steel appliances and quartz countertops is visible in the background. Large sliding glass doors provide unobstructed views of the ocean and nearby palm trees.
Apartment in Wailea
4.94 out of 5 average rating, 306 reviews

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

Top guest favourite
Apartment in Wailea
4.99 out of 5 average rating, 125 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Top guest favourite
A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.
Apartment in Wailea
4.99 out of 5 average rating, 180 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. 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 Not suitable for children or infants.

Top guest favourite
An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.
Guest suite in Wailea
4.99 out of 5 average rating, 128 reviews

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.

Guest favourite
A spacious living area is characterized by wood-paneled walls and natural light from large sliding glass doors. A comfortable queen-sized sleeper sofa and two accent chairs are arranged around a coffee table. A flat-screen smart television is mounted on the wall, adorned with complementary artwork.
Apartment in Wailea
4.89 out of 5 average rating, 104 reviews

Luxury Condo in Wailea Ekahi w/Direct Beach Access

Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

Top guest favourite
An open-concept living area showcases a modern kitchen island with a fruit bowl. A sectional sofa is positioned beside a Samsung Smart TV, with beach-themed artwork adorning the walls. Natural light floods the space, highlighting the neutral tones and inviting layout.
Apartment in Wailea
4.98 out of 5 average rating, 133 reviews

*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

Guest favourite
An inviting pool area is surrounded by lush tropical landscaping. The clear blue water of the pool is complemented by several lounge chairs and tables with umbrellas, providing shaded seating. A serene atmosphere is created by the vibrant greenery in the background.
Apartment in Wailea
4.91 out of 5 average rating, 119 reviews

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.

Guest favourite
A modern kitchen features sleek white cabinets and a spacious granite countertop, with stainless steel appliances. A decorative arrangement of tropical flowers is positioned on the counter. A sliding glass door leads to a private lanai with ocean views, furnished with a dining table and chairs.
Apartment in Wailea
4.96 out of 5 average rating, 182 reviews

Wailea Gem-Remodeled Ocean View

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

Top guest favourite
A comfortable living area features a light blue couch adorned with decorative pillows, accompanied by a wicker chair. A glass coffee table sits atop a textured area rug. Soft lighting is provided by two side lamps, and a decorative surfboard is mounted on the wall.
Apartment in Kihei
4.94 out of 5 average rating, 133 reviews

Top 5% Walk to Beach, Dining & Shops. Pool and AC

Wake up to tropical garden views and walk just steps to golden-sand Kamaole Beach, vibrant cafés, and sunset dining. This centrally located Kihei condo features stylish renovations, 1 full bathroom, a fully stocked kitchen, in-unit laundry, and all the beach gear you need. With pools, hot tubs, and free parking onsite, this is your perfect Maui home base.

Top guest favourite
A spacious studio room is shown, featuring a large bed with dark bedding. Two wall-mounted lights provide illumination beside the headboard, while faux plants are displayed on the wall. A comfortable chair is positioned to the right, and two doors lead to other areas.
Guest suite in Wailea
4.97 out of 5 average rating, 256 reviews

Studio with Large Private Patio!

Stay at a newly renovated studio with a large private patio and entrance. It is based in a quiet South Maui neighborhood, with all the amenities you might need. Your own refrigerator, Television, washer, dryer, microwave, and AC. The private patio is large and surrounded by nature, a perfect spot to unwind after a day of fun.

Popular amenities for Wailea holiday rentals

When is the best time to visit Wailea?

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Avg. price$448 SGD$452 SGD$456 SGD$399 SGD$359 SGD$371 SGD$354 SGD$341 SGD$327 SGD$333 SGD$359 SGD$417 SGD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Wailea-Makena?

    Four-legged friends are welcome in Wailea-Makena. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Wailea-Makena?

    Yes! Work meets play with ease at over 910 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do condo rentals in Wailea-Makena have a gym?

    Absolutely! We offer over 520 condo rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in condo rentals in Wailea-Makena?

    Experience the best of Wailea-Makena with our condo rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly condo rentals in Wailea-Makena?

    Wailea-Makena has more than 690 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Wailea-Makena have wifi?

    Absolutely! We offer over 1,260 condo rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • Are there Wailea-Makena condo rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 1,200 condo rentals with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Wailea-Makena have a bbq area?

    Absolutely! We offer over 590 condo rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Wailea-Makena have air conditioning?

    Absolutely! We offer over 1,220 condo rentals with air conditioning in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Condo Rentals in Wailea-Makena?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 590 homes with a bbq area, over 1,260 homes with wifi, over 520 homes with a gym, over 1,220 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Wailea

  • Total holiday rentals

    Explore 1,910 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 52,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,090 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    1,800 properties feature pools

  • Rentals with dedicated workspaces

    1,130 properties have a dedicated workspace

  • Wifi availability

    1,900 of Wailea holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Wailea rentals

  • 4.8 Average rating

    Wailea stays are highly rated by guests – averaging 4.8 out of 5!

Destinations to explore

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