Have you decided on Wailea as the destination for your next Maui getaway? Then this selection of modern Wailea vacation rentals is for you.
Ten condominium resorts can be found in this chic coastal town, five of which are oceanfront. All have their own unique atmosphere, facilities, and amenities. Whether you’re looking for Wailea villas at a luxury resort or a quaint rental on a private residence, you’ll find it all here.
I hand-picked what I believe are the top Wailea Airbnb and Wailea VRBO listings. The result is a list of stylish Wailea rental condos and villas for all budgets.
Some are a short walk from the beach, but many of them are oceanfront or even beachfront stays. Let’s just say the choices truly are endless. You can take your pick from condos perfect for couples staying in Maui to some Wailea luxury rentals designed for families. All are gated, nicely manicured, and come with access to a resort swimming pool.
So, are you ready to discover the best vacation rentals in Wailea? Then let’s dive in!
In a nutshell
This article features a curated selection of modern condo rentals in Wailea. It has everything from affordable one-bedroom rentals to upscale Wailea condos on the beach. The article concludes with a FAQ section about Wailea vacation rentals.
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Short on time? Here’s a quick list of the top Wailea condo rentals
Wailea vacation rental in the featured image:
Ocean Blue Ohana
Best vacation rentals in Wailea for families:
Wailea Beach Villas Unit E-101 | Ho’olei Villas Unit 15-4
Best beachfront vacation rental in Wailea:
Wailea Elua Village Unit 1002
Best affordable Airbnb in Wailea:
Palms at Wailea Unit 1204
Best luxury Airbnbs in Wailea:
Andaz Maui Unit 8-13 | Ho’olei Villas Unit 15-4
A quick note on VRBO and Airbnb Wailea condos for rent
If you read my informative article on Maui rentals vs. hotels, then you know that I may use Airbnb as a catch-all for vacation rentals. However, I do prefer VRBO as a booking platform over Airbnb. That’s why this article on Wailea condos and villas links to far more VRBO listings than Airbnb listings.
Wailea is the island’s primary luxury resort community and is easily one of the best places to stay in Maui. Beautiful beaches, upscale hotels, fabulous swimming pools, fine dining, chic boutiques, world-class golf resorts, and fancy spas are all part of the fun.
You can learn more about the various things to do in Wailea and how to get around the resort town at the end of the post.
My selection of vacation rentals in Wailea Maui
For every Wailea vacation rental in this list, I have added all the essential details you need. This includes the number of rooms, the number of persons it sleeps, the license number, the average cost per night, and parking inclusions. That way you can see at a glance if the condo is spacious enough and fits within your budget.
Every Wailea rental in this list links out to the corresponding listing on VRBO or Airbnb. Simply read through the details, check the reviews, and set your preferred dates to get an exact breakdown of the costs. If you still like what you see, you can go ahead and make your online booking.
Now, without further ado, here’s my personal selection of the best vacation homes and condos for rent in Wailea Maui.
Psst… At the end of this article, you’ll find a map showing the location of all listings.
1. Spacious condo in the most coveted Wailea vacation rental resort
This contemporary condo is part of Wailea’s most sought-after community: Wailea Beach Villas. This luxury resort community connects to Wailea Beach and is located adjacent to The Shops at Wailea.
Two bedrooms and a sleeper sofa comfortably accommodate up to 6 guests. The open concept of this unit and the large sliding glass doors make it feel very spacious.
There’s a well-equipped kitchen and plenty of amenities to make you feel at home, from a welcome basket to a range of luxury toiletries. The beautiful wooden furniture creates a warm and homey feel.
The outdoor space is just as relaxing thanks to the generously sized covered lanai, comfy seating, and built-in Viking grill.
If that doesn’t sway your decision-making, maybe access to the resort’s heated pool with unforgettable views of Wailea Beach will.
Note that the PH units are the Wailea Beach Villas rentals situated in the Penthouse or Tower building but they’re not all actual top-floor units.
2. Exquisite Wailea beachfront rental for four
If panoramic ocean views and easy beach access are what you’re looking for, then this Wailea vacation rental is for you.
This oceanfront unit features a neutral-toned, modern interior. It forms the perfect canvas for those endless shades of Pacific blue. Two bedrooms and two bathrooms accommodate up to four guests.
The lanai comes with a separate seating and dining area. For those balmy afternoon sunsets overlooking Molokini Crater, head to the lanai with comfy chairs. This Maui condo rental in Wailea also overlooks the communal pool, so a refreshing dip is always on the cards.
In terms of location, Wailea Elua Village is truly blessed. The sprawling grounds of this resort are absolutely fabulous and open up directly to Ulua Beach. Facilities include two large saline swimming pools, a whirlpool spa, and a paddle tennis and pickleball court.
Wailea Elua Village is tucked between the upscale Andaz Maui and the family-friendly Wailea Beach Resort.
To make this Wailea beach vacation rental even more enticing, you’ll find The Shops at Wailea just around the corner.
3. Ground-floor Wailea Airbnb overlooking the fairways
This bright, modern, and sparkling clean ground-level unit overlooks the fairways and the Wailea coast. It’s nestled amidst the manicured grounds of the Wailea Grand Champion resort. This is a quiet and affordable corner of Wailea with a family-friendly setting.
Inside, you’ll find three well-appointed bedrooms, two full bathrooms, an open kitchen, and a living room equipped with a sleeper sofa. This comfortable condo directly overlooks the main pool and BBQ area.
The Wailea Grand Champions vacation rentals are situated along the fairways of the Wailea Blue Golf Course. Also located on-site is the Wailea Tennis Club.
This property is not beachfront but Wailea Beach is located within walking distance. You won’t even miss the beach too much with the resort’s pristine pool and hot tub at your beckoning call.
Many shops and restaurants are even closer. Guests can request a shuttle service to be taken to any destination within the Wailea area.
4. Corner unit with a huge lanai at a Wailea beachfront condo resort
This modern Wailea condo is a corner unit with a huge lanai, allowing you to take in the ocean views from sunrise to sunset. You can also embrace the expansive outdoors thanks to the floor-to-ceiling windows, which provide plenty of natural light for the lounge, kitchen, and dining room.
It has two bedrooms, two bathrooms, and an open kitchen and living area with a sleeper sofa. The elegant decor will make you feel right at home. Plenty of beach gear is provided to maximize family fun. The high-speed WiFi also means you can stream all your favorite shows for a lazy afternoon.
Wailea Ekahi counts as one of the most budget-friendly beachfront vacation rentals in Wailea. It fringes Keawakapu Beach, just south South Kihei and in the northernmost part of Wailea.
The communal area comprises a large pool as well as an outdoor kitchen and BBQ area. Shops and restaurants are just a short walk away.
5. Oceanview condo with high-end finishes
This beautiful unit has been stylishly designed in neutral tones with luxurious touches of leather and wood. There are two bedrooms, two spacious bathrooms, and an open-plan living area with a fully equipped kitchen.
A sliding door system connects the indoor to the outdoor space. The lanai of this well-appointed vacation rental directly overlooks Polo Beach. It’s equipped with plush seating, perfect for a little bit of ‘me time’ in the afternoons with a book in hand.
This Wailea condo is part of the Polo Beach Club resort community. Located in the southernmost part of Wailea, a bit away from the Wailea action and near Makena, this is the perfect place to stay for travelers seeking a more relaxed experience.
The Wailea Beach Path still provides easy access to South Maui’s best restaurants and entertainment. If you’ve gone a lengthy stroll along the beach, then a visit to the resort wellness center with a spa whirlpool may help soothe your muscles.
6. Entire floor of a Hawaiian pole home
Ocean Blue is an Ohana in a convivial residential community called Maui Meadows, just uphill from Wailea. It’s the perfect place to stay in Wailea for a more local experience.
This Wailea vacation rental comprises the entire first floor of a gorgeous Hawaiian pole home. It’s perched at treetop level and surrounded by a mature garden. Add the tapestry of color from the sunrise and sunset into the mix, and you’re in for a real treat.
Ocean Blue Ohana features two bedrooms equipped with luxurious Ritz-Carlton beds, two bathrooms, and an open-plan kitchen and living area with a queen sofa bed. The high beam ceilings and many wooden accents add to the Hawaiian charm.
Sliding glass doors lead to the huge private lanai, where you can find a grill and the most comfy seating arrangements. The jaw-dropping panoramic ocean views are nothing short of phenomenal.
If you prefer a more authentic experience over the typical hotel or condo vacation, then make this place your home. The beaches, shops, and entertainment of Wailea are just a short drive away.
7. Luxury resort penthouse with private jacuzzi at the Andaz Resort
If you like the facilities of a luxury resort on vacation but hate the prospect of being cramped up in a hotel room, then a luxury resort rental makes for the perfect compromise.
Hoomaha Kahakai is an exclusive residence on the site of the luxurious Andaz Maui Resort. It offers everything you need for the perfect trip to Maui.
This exclusive penthouse has three spacious bedrooms. Each comes with its ensuite bathroom with a rain shower and a large tub. The bright open-concept living area is finished with floor-to-ceiling glass doors. There’s also a chef’s kitchen that comes fully stocked.
The spacious lanai is a fabulous place to relax. It offers views over the sprawling resort grounds and the ocean. It’s equipped with a Hestan BBQ grill, an outdoor fridge, and a private hot tub for the true meaning of privacy.
Mokapu Beach is just steps away from this Wailea vacation rental. And to top it off, guests are free to enjoy all the luxury resort amenities of the Andaz Maui Resort. This includes activities like Lei making lessons and yoga or pilates classes, just to name a few.
8. Contemporary condo in Wailea Maui with beautiful views
This fully-stocked Wailea vacation home rental is one of the most affordable options on this list but you really couldn’t tell. The stylish design, excellent finishes, and high-quality appliances give it a fresh and welcoming feel.
It features two bedrooms as well as a queen sleeper sofa in the living room. There’s a spacious lanai that directly overlooks the verdant heart of this resort. Plus, the lanai has some lovely sun loungers for you to soak up some rays.
The condo is perfectly located between Ulua and Keawakapu Beach, so you can take your pick from either beach each day. The complimentary water-sport equipment also means a fun beach day is never far away.
This Mediterranean-style condo is part of the resort community of Palms at Wailea by Outrigger. It’s nestled in a beautifully landscaped tropical garden with ocean views. Palms at Wailea features resort-like common areas including a gorgeous pool and a whirlpool.
The south entrance to Keawakapu Beach is just a 10-minute stroll away.
9. Ho’olei Villa at the Grand Wailea Maui
Next on our list of amazing VRBOs and Airbnbs in Maui is this beautiful vacation home. It’s located in the Ho’olei Resort, a gated luxury villa complex across the street and uphill from the Grand Wailea, A Waldorf Astoria Resort. It offers unobstructed views of the resort area and Wailea Beach.
This prestigious resort complex comes with two pools, a Wailea lazy river, a restaurant, daily housekeeping, and on-site concierge services. The villa features three bedrooms and a total of four beds, sleeping up to eight people, and there are three-and-a-half baths. The indoor area has been tastefully decorated. Sliding glass doors connect the state-of-the-art kitchen and elegant dining area to a spacious lanai with a panoramic dining area and a built-in Wolf grill.
An elevator connects the one-car private garage and laundry room to the main floor.
But this villa’s service goes far beyond these facilities: It also includes access to the spectacular pool complex of the Grand Wailea Resort. That’s right. You can go all out on the pool slides, the swim-in-grotto, the whirlpools, the lazy river, and the waterfalls at no extra cost. It’s the perfect compromise between the lively water facilities of the Grand Wailea Resort and the peaceful setting of the Ho’olei Resort.
Note that not all Ho’olei Maui villas offer Grand Wailea Resort privileges. So, if this particular listing isn’t the right fit for you and you decide to browse through the other Ho’olei listings on VRBO, then be sure to read the fine print. The price point can be an indication.
10. Cozy one-bedroom Wailea Airbnb near the golf course
This modern and elegant ground-floor condo is a budget-friendly option for a couple or a small family. It comes with a spacious bedroom, two full bathrooms, a cozy living room with a sleeper sofa, and a clean and fully equipped open kitchen.
Thanks to the unit’s slightly elevated location, the lanai offers unobstructed views over the ocean and over the neighboring islands of Lanai, Molokini, and Kahoolawe.
Guests are welcome to enjoy the swimming pools and barbecue facilities of the resort community.
Wailea Ekolu Village is located uphill, between the base of the Haleakala Volcano and the Wailea Blue Golf Course. There are two swimming pools for guests to enjoy. The lush tropical foliage and beautiful views make it a wonderful place to retreat to after a day of exploration.
11. Stunningly designed condo with panoramic ocean views
Next on our list of best Wailea vacation rentals is this exquisite luxury condo. It features two meticulously appointed bedrooms, three resort-like bathrooms, a fully stocked open kitchen, and a living area that bathes in natural light. All finishes are top-notch. The postcard views are phenomenal. There’s also a beautiful lanai which is equipped with a BBQ grill.
This tastefully decorated unit is located at one of the most privileged locations in Wailea. Think of an ocean-view resort property tucked away between the Four Seasons Resort Maui and the Fairmont Maui Kea Lani, right in between Wailea Beach and Polo Beach.
Because the Wailea Point Village resort community imposes a 30-day minimum rental period, it’s often overlooked by the average visitor to Maui. But it’s one of the best options for long-term vacation rentals in Wailea Maui. This community is so exclusive that only about a handful of rentals are available on VRBO and Airbnb. This gorgeous gem is one of them.
Guests enjoy access to the luxurious facilities of this resort. There are three pools (one of which is a lap pool), cozy pool pavilions, tennis courts, paddle courts, a fitness center, and even a herb garden. There isn’t much more you could ask for from a long-term stay.
12. Luxurious ground-floor condo with private plunge pool
Let’s conclude this list of Wailea vacation rentals with one of the most stunning Wailea Beach Villas. If it’s the perfect blend of contemporary Mediterranean stay with accents of authentic Hawaiin finishings you seek, then this rental is for you
This ground-floor unit is perfect for families. It comes with a grassy area and a plunge pool in addition to the beautiful lanai. Plus, this is one of the villas closest to the family pool. The beach, restaurants, and shops are all within easy walking distance.
Inside, you’ll find three bedrooms, three bathrooms, and a cozy seating area with high-end, plush furniture. And let’s not forget the gourmet kitchen, which is sure to please the designated chef. This unit is very well-appointed with high-end finishes throughout.
You may be missing those expansive ocean views, but that’s a small compromise for the intimate setting provided by the lush garden. Besides, you can always take a short walk to the beach for those mesmerizing sunsets on the golden sands.
Map of all the listed VRBO & Airbnb rentals in Wailea Maui
For your convenience, I created this map showing the location of all listings by listing number.
What are the best things to do in Wailea Maui?
Before embarking on your journey to this stunning destination, why not plan some fun activities? Here’s a brief overview of some must-do activities in this luxurious resort area:
Wailea may lack the action, but you can find plenty of activities in the nearby South Maui towns of Kihei and Makena. Go on a snorkeling tour, swim with turtles, hike the Hoapili trail, or go horseback riding.
If you’re looking to explore more of Maui, then I’d strongly recommend renting a car. My go-to partner is Discount Hawaii Car Rental. Their booking process is effortless, with no booking fees, prepayment, or cancellation penalties!
General booking policies of Wailea Maui condos for rent
There are loads of cancellation and booking policy settings that VBRO and Airbnb renters can implement. So, to help protect you when booking your stay, it’s ideal to look for properties that have the following policies:
Wailea VRBO and Airbnb booking policies to look for
Wailea VRBO and Airbnb cancellation plans to look for
Which of these Wailea vacation rentals caught your eye?
Chances are that you’ve found your dream rental for that long-awaited Maui vacation. If not, then have a look at my other wish lists to discover even more amazing Maui vacation rentals.
Also, rest assured that all featured rental condos in Wailea are operating legally with the required county permits and that all suggestions are hand-picked and thoroughly researched.
Wailea vacation condos and house rentals FAQ
You may still have some pressing questions about Wailea vacation rentals. Here are all the answers to put your mind at ease.
