Wailea villas
We found 71 villas — enter your dates for availability
Explore Wailea villa rentals
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
~ This Is Wailea Living ~
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Stunning Ocean View Wailea Beach Villa- Book & Save
Sleeps 9 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Luxe Townhome, Ocean Views, Relax by the Pool
Sleeps 10 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
I.P.M PRESENTS: HOOLEI 93-1: 3 BEDROOMS + OFFICE. FLEXIBLE CANCELATION POLICY
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Top rated villa rentals - Wailea
The best location!
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
2024 Christmas Vacation to Maui
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Perfect for families
1010 out of 10
Exceptionalexceptional
120 reviews(120 reviews)
Big thumbs up!!
1010 out of 10
Exceptionalexceptional
55 reviews(55 reviews)
Perfect
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Great condo
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Maui Family Time
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
60th Birthday Celebration
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Find spaces that suit your style
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More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Are there any vacation villa rentals in Wailea?
Check out the 71 villa rentals in Wailea that offer more space than traditional hotel rooms, making them ideal for group or family vacations. Consider basing yourself in the sought-after neighborhood of Halama Street and then explore the city like a local.
How much does it cost to stay in a villa rental in Wailea?
A range of factors will determine the price of a villa rental in Wailea, such as the size of the property and how long and when you’re staying. All you need to do is enter your travel dates and any preferences to find a villa that fits your budget and style.
When is the best time to rent a villa in Wailea?
With average temperatures of between 25ºC (77ºF) and 27ºC (81ºF), August is when the majority of our guests book a villa rental in this corner of Kihei. If you plan to travel to Wailea at this popular time, book ahead for the best availability.
Where can I rent a Wailea villa with great views?
If you’re looking for a good way to relax after an action-packed day, put your feet up and gaze at the gorgeous views from your villa rental. Use our filters to tailor your search for properties that’ll add a little scenic wonder to your Wailea vacation. Our “Location” filter is an excellent place to begin.
Can I book a luxury villa in Wailea?
Featuring a range of amenities like private pools, beautiful courtyards and modern technology features, Vrbo’s luxury villa rentals in Wailea promise a sophisticated travel experience. Look forward to enjoying the finest in comfortable quality furnishings, plenty of room and an atmosphere that ensures a relaxing getaway for you and your guests.
What are the top things to do in Wailea?
One of the first things to do after locking in your villa rental is to fill your schedule with memorable activities. There’s plenty of them in Wailea, with some of the best family-friendly attractions including Wailea Beach, Maui Ocean Center and Kamaole Beach Park.
Why should I book my villa vacation with Vrbo?
With attentive customer support available 24/7, peace of mind is guaranteed when you book through Vrbo. From the second you lock in your villa rental to even after your trip is over, we’ll be by your side every step of the way. It’s all part of our Book with Confidence Guarantee. Plus, we also have a secure payment process and flexible cancellation policies