Wailea holiday homes

We found 1,428 holiday rentals — enter your dates for availability

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October 2025

November 2025

Find the perfect place for you stay in Wailea by choosing from 61 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:2 Jan - 9 Jan

Wonderful

(7 reviews)

Wailea Luxury Retreat | Walk to Beach & Shops

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$1,866 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

NZ$1,184 per night

includes taxes & fees

Exceptional

(107 reviews)

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

Kihei, HI

13% off

for 7 nights, 1 apartment

NZ$2,508 per night

includes taxes & fees

Exceptional

(56 reviews)

Mana Kai 607 Great Ocean Views, Best Beach on Maui

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$1,636 per night

includes taxes & fees

Exceptional

(92 reviews)

5 Star Ocean View, Beach House Chic, Click the Video tour below!

Kihei, HI

7% off

for 7 nights, 1 villa

NZ$1,229 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

8% off

for 7 nights, 1 apartment

NZ$938 per night

includes taxes & fees

Welcome Basket with snacks and info for condo & property.

Exceptional

(64 reviews)

SPACIOUS LUXURY - OWNER DIRECT - OCEAN peek-a-VIEW

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$884 per night

includes taxes & fees

Exceptional

(91 reviews)

Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

Kihei, HI

7% off

for 7 nights, 1 home

NZ$2,021 per night

includes taxes & fees

Gorgeous views of the ocean and Maalaea Bay. Great for whale watching.

Exceptional

(106 reviews)

Upgraded unit with Panoramic Ocean and Mountain Views

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$1,067 per night

includes taxes & fees

Early evening glow before sunset from our lanai

Exceptional

(85 reviews)

Tropical Garden End Unit A/C with Ocean & sunset Views! Walk to Keawakapu Beach!

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$790 per night

includes taxes & fees

Exceptional

(131 reviews)

BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!

Kihei, HI

7% off

for 7 nights, 1 apartment

NZ$960 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

Premier Host

to be done again

We recently had the pleasure of staying at a beautiful property in Wailea. The place was immaculately presented, boasting cleanliness and abundant sunshine. The views were simply breathtaking, and the amenities provided were top-notch. The property’s location was incredibly convenient, being just a short stroll away from the beach, shops, and a variety of restaurants. Despite its central location, the place was peaceful and quiet, providing a serene retreat from the hustle and bustle. One of the highlights of our stay was the stunning sunset views from our balcony. It was truly a sight to behold and made our evenings all the more special. This place proved to be the perfect holiday spot for relaxation and quality time with friends and family. We couldn’t have asked for a better experience and highly recommend it to others looking for a memorable stay in Wailea.

Pablo G.

Stayed Apr 2024

Ocean view from your private lanai & outdoor dining

Premier Host

Perfect in every way

Fantastic location with beach, pools and garden at your doorstep. Plenty of room for two couples or a family. Walking distance to shops and restaurants. Great for the 3 Wailea golf courses nearby. Communication with host was prompt and very helpful. Highly recommended to all future holiday makers.

Louise O.

Stayed Sept 2023

Premier Host

Peace, quiet and comfort.

The Villa Paola was ideal for me travelling alone - if anything it was probably more than I needed but it had all the conveniences and the environment that I required. I will definitely be sharing my memories of this Villa with friends and family. Thank you Marcello for a wonderful stay.

Michael T.

Stayed Sept 2022

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
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
More space, more privacy, more amenities — more value

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, Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach. 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, Bookabach 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 Bookabach'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 Bookabach.

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 Bookabach, 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.