Holiday houses 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
Condo 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.
Condo 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
A modern living area showcases a spacious L-shaped sofa adorned with blue accent pillows. A circular coffee table sits at the center, complemented by two stylish armchairs. Natural light floods the room through large windows, highlighting the green artwork mounted on the wall.
Condo in Wailea
4.95 out of 5 average rating, 165 reviews

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.

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, 134 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.

Top Guest favourite
A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.
Condo in Wailea
4.96 out of 5 average rating, 166 reviews

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

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.
Condo in Wailea
4.9 out of 5 average rating, 109 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
The living room features a comfortable gray sofa adorned with decorative pillows, a ceiling fan, and large sliding doors that open to a lanai with views of the ocean. A light wooden side table and a TV unit complement the space, enhancing a relaxing ambiance.
Condo in Kihei
4.98 out of 5 average rating, 192 reviews

180° Ocean views • Luxe condo • Steps to Beach

Enjoy panoramic ocean & sunset views year round from, Kihei Lani, a 5th floor luxury condo that artfully blends contemporary design, modern amenities and island style. Full, whisper quiet AC in all rooms! Ideally located in Kihei, the condo is right across the street from the best beaches on Maui and is walking distance to excellent restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Guest favourite
Home in Wailea
4.96 out of 5 average rating, 455 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Top Guest favourite
The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.
Townhouse in Wailea
4.97 out of 5 average rating, 136 reviews

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

Top Guest favourite
The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.
Condo in Wailea
4.98 out of 5 average rating, 150 reviews

130K Hawaiian Reno on Wailea Blue Golf *Ocean View

BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

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.
Condo in Wailea
4.96 out of 5 average rating, 188 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
Condo in Wailea
4.97 out of 5 average rating, 197 reviews

Ocean/Golf Course Views, Tropical Resort in Wailea

Breathe in and exhale slowly while gazing at 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.)

Popular amenities for Wailea holiday rentals

When is the best time to visit Wailea?

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Avg. price$508 AUD$513 AUD$517 AUD$453 AUD$408 AUD$421 AUD$402 AUD$387 AUD$371 AUD$396 AUD$452 AUD$533 AUD
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Frequently Asked Questions

  • What types of vacation rentals are available in Wailea-Makena?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Wailea-Makena. From over 50 house rentals to over 1,460 condo rentals, we've got you covered.

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

    Yes! Work meets play with ease at over 1,130 vacation rentals in Wailea-Makena featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Four-legged friends are welcome in Wailea-Makena. Choose from more than 10 vacation rentals for guests traveling with pets.

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

    Experience the best of Wailea-Makena with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 10 homes with a gym, over 20 homes with self check-in, over 120 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

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

    Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Wailea-Makena, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Wailea-Makena have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wailea-Makena have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 120 house rentals with a bbq area in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 10 house rentals with a gym in Wailea-Makena. Enjoy a tailored experience with all the comforts you desire.

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 $102 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    1,900 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!

Destinations to explore

  1. Airbnb
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  3. Hawaii
  4. Maui County
  5. Wailea