Wailea holiday rentals

We found 1,399 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Wailea by choosing from 51 houses, 28 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:23 Oct - 30 Oct

Image gallery for Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)

Tropical upper pool at Maui Kamaole
9.8 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)

Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)

Kihei

7% off
Price is AU$4,014
for 7 nights, 1 apartment
AU$573 per night
includes taxes & fees
Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)

Find spaces that suit your style

  • 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

Why visit Wailea

  • Scenic coastal trails: Enjoy the breathtaking views along the Wailea Coastal Walk and beach promenades.
  • Pristine beaches: Relax on immaculate sandy shores ideal for sunbathing and water activities.
  • Outdoor adventures: Engage in various sports and leisurely strolls in a family-friendly environment.
  • Art and culture: Discover local art galleries that add a vibrant touch to the neighbourhood.
  • Upscale retreat: Experience a tranquil escape with luxurious amenities and natural beauty.

Popular types of accommodation around Wailea

Wailea, nestled in Kihei, Hawaii, is renowned for its stunning beaches and luxurious resorts. This upscale neighbourhood offers a tranquil escape with a range of attractions, including pristine golf courses, beautiful coastal trails, and vibrant art galleries. Whether you prefer a condo with ocean views or a private holiday home, Wailea holiday rentals provide the perfect base to explore the breathtaking scenery and indulge in a variety of outdoor experiences. Discover the charm of Wailea and enjoy a memorable Hawaiian getaway.

  • Condos: The top choice for holidaymakers in Wailea, condos offer a blend of comfort and convenience, ideal for enjoying the local scenery.
  • Private Holiday Homes: A popular option for those seeking more space and privacy, these homes provide a home-like atmosphere for families and groups.
  • Apartments: Perfect for shorter stays, apartments offer essential amenities in a compact setting, catering to solo travellers and couples alike.
  • Villas: Offering luxury and spaciousness, villas are an excellent choice for those desiring an upscale experience during their holiday.
  • Cottages: Quaint and charming, cottages provide a delightful retreat for those looking for a more intimate and cosy holiday experience.**

Top attractions in and around Wailea

Wailea, nestled in Kihei, Hawaii, is a stunning destination perfect for beach and outdoor enthusiasts. Visitors can enjoy the scenic Wailea Beach Walk, explore the picturesque Wailea Jewel, and partake in various sports activities. The Wailea Coastal Walk offers breathtaking views, making it an ideal spot for sightseeing. With its blend of natural beauty and family-friendly experiences, Wailea promises a memorable holiday for all travellers.

  • Wailea Beach: A pristine stretch with quintessential beach vibes, perfect for leisurely strolls and sunbathing in Wailea.
  • Makena Beaches: A national state park offering stunning outdoor scenery and adventurous experiences, ideal for exploring nature within Wailea.
  • Kamaole Beach Park 3: An urban park 3km from Wailea, blending family-friendly outdoor fun with a touch of city ambience.

Things to do recommended for couples

Wailea offers a perfect romantic getaway. Enjoy a sunset beach walk along the golden sands of Wailea Beach or indulge in a couples' massage at a luxurious spa. For a unique experience, take a scenic helicopter tour over the stunning Hawaiian coastline.

Things to do recommended for families

Families will love the stunning beaches of Wailea, perfect for building sandcastles and swimming. Visit the nearby Maui Ocean Centre to explore fascinating marine life, or enjoy a family-friendly hike at the scenic Makena State Park for breathtaking views and a chance to spot local wildlife.

Things to do recommended for groups

Explore the stunning beaches of Wailea, indulge in a delightful luau experience, or embark on a group snorkelling adventure at Molokini Crater. Enjoy a scenic hike through the lush landscapes of Haleakalā National Park, where breathtaking views await.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Wailea

If you're travelling with a group, as a family, bringing your pets, or seeking longer stays, it's important to filter according to your key preferences. Here are some helpful booking tips for Stayz.

  • Traveling to Wailea with a group: Think about how many bedrooms you will require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Fortunately, you can easily refine your search for these options and many more on Stayz.
  • Traveling to Wailea with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Wailea: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea: If you're seeking holiday lets offering long-stay deals, you've come to the right place. By using the appropriate filters, you can effortlessly locate and save on monthly rentals. You might also consider including amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Wailea

Wailea offers a captivating retreat with pristine beaches and stunning coastal views. Ideal for a romantic and relaxing holiday, this neighbourhood boasts beautiful wailea beach and a vibrant wailea village. Stroll along the wailea cost and experience the charm of the local resort community. Enjoy an unforgettable maui holiday immersed in natural beauty and a family-friendly atmosphere, all within the serene embrace of Wailea.

  • Maui: Maui is a stunning island that beckons visitors with its breathtaking beaches and outdoor adventures. Located approximately 16km from Wailea, this tropical paradise offers a wealth of activities, from golfing on world-class courses to exploring vibrant shopping centres. The island is renowned for its picturesque landscapes, including family-friendly beaches and tranquil bays, making it an ideal spot for relaxation and exploration. Whether you're soaking up the sun or indulging in local cuisine, Maui promises a memorable experience for all travellers.
  • Kihei: As a vibrant city situated in close proximity to Wailea, Kihei is a hotspot for beach lovers and outdoor enthusiasts. The area is known for its stunning coastline, inviting visitors to engage in various water sports or simply bask in the sun. With numerous golf courses and well-equipped shopping centres, Kihei caters to both relaxation and recreation. Urban parks also add to the charm of this locale, providing green spaces for picnics and leisurely strolls. Kihei's lively atmosphere and beautiful scenery make it a must-visit destination.
  • South Maui: Located a mere 805m from Wailea, South Maui is a delightful area that offers a blend of family-friendly activities and natural beauty. This picturesque region is perfect for those seeking beach days and outdoor adventures, with an array of shopping centres and malls to explore. The local attractions, including scenic urban parks and stunning beaches, create an inviting environment for families and nature lovers alike. South Maui's charm and accessibility make it a fantastic addition to your holiday itinerary.

Best time to go to Wailea

If you're planning a trip to Wailea, it's a good idea to check both the weather and property rates. The warmest months are August and September. Peak season runs in January and March to April, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January72.7°F (22.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
February72.3°F (22.4°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.7°F (22.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April74.1°F (23.4°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May75.6°F (24.2°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
June76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageAverage
July77.9°F (25.5°C)No Rain (Dry)Mostly SunnyAverageAverage
August78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
September78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
October77.7°F (25.4°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
November75.7°F (24.3°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December73.8°F (23.2°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Stayz is a breeze

Looking to save on your next holiday? Consider remaining flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay may offer significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday accommodation.

Stayz Trips: Planning as easy as it gets

Stayz's inventive Trip Board offers you a dedicated area to craft new journeys, pick up where you last left off, or review and organise your plans. Properties you have previously saved or booked are now categorised under Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

The information above was last updated:

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.

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