Holiday rentals in Wailea

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Top-rated holiday rentals in Wailea

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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, 217 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, 310 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
A bright living area features sliding glass doors that open to a private lanai with ocean views. Comfortable seating options include a cozy sofa and armchair, complemented by a round coffee table and decorative pillows. Natural light fills the space, creating a welcoming ambiance.
Apartment in Kihei
4.97 out of 5 average rating, 154 reviews

Stunning Ocean Views

Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

Top guest favourite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Apartment in Kihei
4.99 out of 5 average rating, 249 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to 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
A serene lanai space is presented, featuring tiled flooring and tropical views. Two comfortable chairs with blue cushions are positioned alongside a small table. Sunlight filters through, highlighting vibrant greenery and swaying palm trees in the background, contributing to a relaxing atmosphere.
Apartment in Wailea
4.85 out of 5 average rating, 383 reviews

Enjoy while you can, Charming Wailea Studio

Legal, active studio in Wailea with charming views of palm trees and a sparkling blue pool. Our place is close to the beach, family-friendly activities, Shops of Wailea, many Wailea Hotels: Andaz, Fairmont, Marriott Four Seasons Hotel, etc., restaurants, golf courses, tennis court. You’ll love my place because of the comfy bed, big TV, the views, overlooking pool and palm trees with easy access straight down to pool/jacuzzi/BBQ from your lanai.

Guest favourite
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.
Apartment in Wailea
4.9 out of 5 average rating, 119 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.

Guest favourite
Home in Wailea
4.96 out of 5 average rating, 451 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
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.
Apartment in Kihei
4.98 out of 5 average rating, 184 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 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.
Apartment 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.

Superhost
A spacious living area is featured with comfortable seating, a large television, and natural light streaming through generous glass doors. A private lanai is highlighted with a dining table for four, surrounded by lush greenery. The bedroom showcases a king bed with calming decor, while a tranquil pool and palm trees are visible outside.
Apartment in Wailea
4.81 out of 5 average rating, 171 reviews

Last Minute Deal! Wailea Condo Oceanfront Complex

Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

Popular amenities for Wailea holiday rentals

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Quick stats about holiday rentals in Wailea

  • Total holiday rentals

    Explore 1,900 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at £51 per night before taxes and fees

  • Verified guest reviews

    Over 52,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,080 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

    1,890 of Wailea holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.8 Average rating

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

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