Maluaka Beach featuring landscape views, tropical scenes and a sandy beach

Wailea holiday rentals

We found 1,357 holiday rentals — enter your dates for availability

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Flexible dates

October 2025

November 2025

Find the perfect place for you stay in Wailea by choosing from 60 houses, 40 apartments and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Wailea

Showing deals for:16 Jan - 23 Jan

Exceptional

(81 reviews)

Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

Kihei, HI

15% off

for 7 nights, 1 apartment

AU$1,188 per night

includes taxes & fees

Exceptional

(147 reviews)

Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,147 per night

includes taxes & fees

Exceptional

(36 reviews)

Beachfront Condo E 303/ Incredible views/Pickleball/Great Snorkeling

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$2,296 per night

includes taxes & fees

Wonderful

(34 reviews)

Beautiful, Palms At Wailea Condo #608- 2BR/2BA,GREAT LOCATION OCT /Nov SPECIAL

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$869 per night

includes taxes & fees

Views of Kahoolawe & Molokini from 2nd story lanai.

Exceptional

(102 reviews)

NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA

Kihei, HI

7% off

for 7 nights, 1 home

AU$1,029 per night

includes taxes & fees

You'll love the lanai which is right near the sunken pool area, creating quiet

Exceptional

(46 reviews)

Maui Kamaole, 2 lanais, queen sofa beds, quiet, eco friendly, south Kihei condo

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$725 per night

includes taxes & fees

Adult Pool with Spectacular Views of the Pacific Ocean and Wailea Beach

Exceptional

(144 reviews)

The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!

Kihei, HI

8% off

for 7 nights, 1 apartment

AU$2,818 per night

includes taxes & fees

Exceptional

(41 reviews)

WOW!!! Great Winter Special Minutes from the Beach. NEW AC for your Perfect Stay

Kihei, HI

5% off

for 7 nights, 1 apartment

AU$745 per night

includes taxes & fees

Exceptional

(95 reviews)

D211 Quiet & Private 2br2ba near Wailea 2025 Discount 15% 7 nts or more.

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$758 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Wailea

Wailea Beach

Find the best place to stay - Wailea

Stunning views from entire dining/living area

Premier Host

Breathtaking Ocean Views! Beach Front Luxury Penthouse, Polo Beach 2 Bed/2 Bath

Sleeps 5 · 2 bedrooms · 2 bathrooms

Breathtaking view from the adults only Makai pool

Premier Host

Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

Sleeps 8 · 3 bedrooms · 3 bathrooms

The Serene Natural Adult Quiet Oceanside Pool & Spa at The Beach Villas

Premier Host

20% OFF 10/25-11/1/25 BEACHFRONT WAILEA PANORAMIC OCEAN VIEWS 4Bd 3BA 3892 s.f.

Sleeps 8 · 4 bedrooms · 3 bathrooms

Top rated rentals - Wailea

Keawakapu Beach - 1/4 mile from condo - 7 minute walk

Premier Host

Fabulous Maui

There are no words to describe how wonderful our stay was the condo was so beautiful and so Hawaiian the decor was amazing so much thought went into everything there was nothing that was lacking We have stayed in many condos in Maui but this one tops the list Thank you so much Rose for making our stay so perfect We can’t wait to come back

Roger L.

Stayed Nov 2023

Updated kitchen cabinets and countertops,

Wonderful stay in Maui

Fantastic property in a great location! Communicative, friendly hosts and clean, perfectly suited apartment in quiet, relaxing Grand Champions.

Alison T.

Stayed Apr 2023

Premier Host

Condo Luxury

I’m sure we are all concerned whether the property we rent will live up to the marketing hype and the clever photo shoot. This property is exactly as described. It’s extremely clean, spacious, very well appointed and was recently renovated to a very high standard. Faye (the owner) has set a standard that other property owners should aspire to achieve. Sadly, most don’t and are just full of excuses when their lackluster offerings are found to be wanting. Thanks Faye, you have a wonderful eye for detail...it was fantastic to stay at your property! Hopefully we will be able to come back next year. Cheers Michael and Jools

Michael G.

Stayed Aug 2022

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
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Frequently asked questions

What is the most popular type of holiday home accommodation in Wailea?

Condos are the most popular style of holiday home in Wailea, according to our data. Even if you have something a little different in mind, Stayz has properties in loads of sizes and shapes. Browse our many options to find your perfect match.

How much does it cost to rent a holiday home in Wailea?

The average price for a holiday home in Wailea is based on a number of factors, like time of year, length of stay and property type. Whether you prefer a sprawling villa with lots of bedrooms or a quaint cabin ideal for just you and the kids, just enter your dates of travel to view stays with great value.

How much does it cost to rent a beach house in Wailea?

The average price for a holiday home near the beach in Wailea depends on when you're visiting the area and the type and size of property you're searching for. You can easily and quickly find prices on Stayz by entering the dates you'll be travelling. Then use the handy filter tool to select the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday homes in Wailea?

You're in luck. There are. You can pick from 1 ,198 holiday homes that welcome pets in Wailea on Stayz. Our furry friends need a break too, so simply use our search function for pet-friendly holiday homes to book a perfect pad where your puppy dog can join in the fun.

Can I rent a house with a pool in Wailea?

Mark the "pool" box in our handy filter tool and select from 1 ,089 houses with private pools in Wailea on Stayz. Morning dip, sunset soak or midnight swim? Downtime is up to you when your holiday property comes with its own pool.

What are popular home amenities in Wailea?

The most popular home amenities people look for in Wailea include a fireplace, a chef and tennis. Whether you're on a trip with family, friends or even pets, Stayz holiday properties provide the best amenities for beginning new traditions with the people closest to you.

Are there large group holiday homes in Wailea?

Wailea has nine holiday homes that can fit 10 or more guests. These stays come with plenty of space to share good times with your favourite people.

Are there holiday homes in Wailea that welcome kids?

Wailea has 1 ,194 family-friendly holiday homes to pick from. And securing a stay that welcomes little ones is simple with Stayz's "Properties good for families" filter. As well as having the whole place to yourselves, you'll enjoy access to perks and amenities like dining rooms, kitchens and yards.

What are the top attractions for families in Wailea?

There are loads of fabulous things to do and see with the family in Wailea, such as:

Wailea Beach
Kamaole Beach Park
Keawakapu Beach North

Are there one-bedroom holiday homes in Wailea?

Yes, you'll find 361 one-bedroom properties in Wailea to pick from. A one-bedroom holiday home is a great choice if it's just you and your partner or if you're holidaying alone. Throw in more privacy, convenience and space compared to a regular hotel, and you've got the makings of a getaway to remember.

Can I find two-bedroom holiday homes in Wailea?

Gather your family and enjoy peace, privacy and comfort in one of the 630 two-bedroom holiday properties Wailea has to offer.

Are there holiday homes with WiFi in Wailea?

You'll find 603 holiday homes with WiFi in Wailea. If you'd like to disconnect from daily life on your trip, but still need to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Wailea?

Pick from 1 ,019 holiday homes with air conditioning in Wailea providing that cool, cool breeze and extra element of comfort. Enter your desired travel dates and then use our handy filter tool to find properties with air conditioning.

How old do you have to be to rent a holiday home in Wailea?

The minimum age is normally 16, 18 or 21. It can differ from one property to another on Stayz, so check the rules of your chosen Wailea holiday home before making a booking.

How long can I rent a holiday home in Wailea for?

The amount of time you can stay in a Wailea holiday home for is up to the property. Just enter your dates of travel to find options offering longer term stays. They come with all you require to make your extended getaway more enjoyable and convenient, like air conditioning and kitchens. Some holiday homes may also offer weekly or monthly discounts, so you can stay longer for less money.