Condo vacation rentals in Wailea

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Top-rated condo rentals in Wailea

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Top guest favorite
A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.
Condo in Wailea
4.99 out of 5 average rating, 211 reviews

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 an ideal location, right on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5 star resorts 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 Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

Top guest favorite
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.
Condo in Wailea
4.94 out of 5 average rating, 305 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 favorite
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 favorite
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 favorite
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 Wailuku
4.98 out of 5 average rating, 104 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.

Guest favorite
The spacious living area features vaulted ceilings with exposed beams and large glass doors that open to stunning ocean views. Comfortable seating includes two patterned armchairs and a cozy sofa. A coffee table is centered in the room, and the dining area is illuminated by pendant lights.
Condo in Wailea
4.97 out of 5 average rating, 117 reviews

Upscale and Elegant Vistas

Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

Guest favorite
A view from the second floor displays lush tropical landscaping with palm trees and vibrant greenery. The ocean is visible in the background, framed by a clear blue sky. The scene offers a serene outdoor ambiance typical of Wailea.
Condo in Wailea
4.9 out of 5 average rating, 116 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

Top guest favorite
A modern dining area features a polished wooden table surrounded by six chairs. Natural light floods the space, highlighting the contemporary kitchen with granite countertops in the background. Large sliding glass doors open to a scenic view of the ocean and lush surroundings.
Condo in Wailea
4.94 out of 5 average rating, 186 reviews

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.

Top guest favorite
A bright and airy studio space features a spacious bed with layered bedding and a decorative throw. A private lanai with seating is visible through expansive glass doors, providing views of surrounding tropical greenery. The room is equipped with modern comforts, including air conditioning.
Condo in Kihei
4.98 out of 5 average rating, 182 reviews

Steps to Beach, Shops & Dining w Views!

Exquisitely remodeled top floor studio condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches & restaurants and lounge in the multiple pools & hot tubs on property! Everything is recently remodeled and stocked with everything you'll need to feel right at home (including 2 beach chairs and a beach umbrella).

Top guest favorite
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, 143 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 favorite
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.
Condo 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 favorite
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, 181 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.

Popular amenities for Wailea condo rentals

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MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ1,219ﺩ.ﺇ1,267ﺩ.ﺇ1,263ﺩ.ﺇ1,102ﺩ.ﺇ962ﺩ.ﺇ988ﺩ.ﺇ955ﺩ.ﺇ922ﺩ.ﺇ889ﺩ.ﺇ914ﺩ.ﺇ1,003ﺩ.ﺇ1,146
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Quick stats about condo rentals in Wailea

  • Total vacation rentals

    Explore 1,260 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 40,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    690 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    1,200 properties feature pools

  • Rentals with dedicated workspaces

    690 properties have a dedicated workspace

  • Wi-Fi availability

    1,260 of Wailea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wailea rentals

  • 4.8 Average rating

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

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