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 $139 NZD per night before taxes and fees

  • Verified guest reviews

    Over 55,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,140 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

    1,120 properties have a dedicated workspace

  • Wi-Fi availability

    1,930 of Wailea holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace 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.

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Top Guest favourite
Condo in Wailea
4.99 out of 5 average rating, 132 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 spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Condo in Maalaea
4.98 out of 5 average rating, 119 reviews

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

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, 193 reviews

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.

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, 142 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
Condo in Wailea
4.97 out of 5 average rating, 110 reviews

Modern Renovated Palms at Wailea Condo!

MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Top Guest favourite
A spacious living area featuring high vaulted ceilings and large windows offering ocean views. Comfortable seating arrangements include an oversized sofa and stylish armchairs. A dining table accommodates four, complemented by a decorative feature wall. Natural light enhances the airy atmosphere throughout the room.
Apartment in Wailea
5 out of 5 average rating, 103 reviews

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.

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.
Condo in Wailea
4.99 out of 5 average rating, 149 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
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
4.97 out of 5 average rating, 160 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
4.95 out of 5 average rating, 198 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
4.98 out of 5 average rating, 203 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.)

Top Guest favourite
A light-filled living room features a large gray sectional sofa and a 70-inch Smart TV mounted on the wall. Above the TV, a colorful 'ALOHA' sign is displayed. Sliding glass doors offer views of a spacious lanai overlooking lush green fairways.
Condo in Wailea
5 out of 5 average rating, 135 reviews

Wailea Surf Shack: Golf, shopping & beaches!

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.

Top Guest favourite
A vibrant sunset casts warm orange and yellow hues over the ocean, with waves gently lapping at the shore. Silhouetted palm trees and lush greenery frame the scene, while rocky outcrops jut into the water, creating a picturesque coastal landscape.
Condo in Wailea
4.99 out of 5 average rating, 182 reviews

Romantic, Luxury Condo with Spectacular Ocean View

Our luxury condo in the heart of Wailea is close to the beach and world class golf. You’ll love our condo because of the beautiful upgrades, the high ceilings, the kitchen, the comfy bed, the wonderful sea breezes and the spectacular ocean views. Our condo is romantic and great for couples.

Popular amenities for Wailea holiday rentals

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  3. Hawaii
  4. Maui County
  5. Wailea
  6. Wailea