Wailea holiday homes

We found 1,360 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Wailea by choosing from 52 houses, 29 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 Oct - 9 Oct

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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

    More space, more privacy, more amenities — more value

Why visit Wailea

  • Pristine Beaches: Enjoy the sun and surf on Wailea Beach and Keawakapu Beach, ideal for a relaxing seaside escape.
  • Scenic Coastal Walks: Stroll along miles of coastal paths and take in the breathtaking ocean views.
  • Urban Parks and State Parks: Explore lush parks offering family-friendly outdoor adventures and picnicking spots.
  • Wailea Village: Discover unique shops and diverse dining options in a vibrant local setting.
  • Romantic Atmosphere: Experience a tranquil and enchanting ambiance perfect for couples and families.

Top attractions in and around Wailea

Wailea in Kihei, Hawaii is a splendid coastal neighbourhood ideal for beach, outdoor, and scenic holidays. With its pristine beaches, urban parks, and state parks, the area offers an abundance of family-friendly experiences and serene outdoor adventures. It’s the perfect destination for travellers from New Zealand seeking a blend of relaxation and exploration in a vibrant yet tranquil setting.

  • Wailea Beach: Enjoy a laid-back beach vibe right in Wailea, perfect for soaking up the sun and taking refreshing dips in the clear Pacific waters.
  • Ahihi-Kinau Natural Area Reserve: Explore rugged coastal terrain with romantic excursions, offering a unique blend of nature and adventure within Wailea.
  • Kalama Beach Park: Experience a vibrant urban park with family-friendly outdoor activities, located 5km away, ideal for a day out in the city.

Things to do recommended for couples

Looking for a romantic escape in Wailea? Enjoy a scenic coastal drive to Kihei, savour local cuisine and explore charming art galleries. Experience authentic island life with a sunset walk along the beach. A perfect getaway for a couple seeking a relaxed and memorable holiday.

Things to do recommended for families

Families will relish kiwi-friendly adventures in Wailea, Kihei, enjoying scenic beaches and engaging local cultural activities, perfect for sparking the imagination of young explorers.

Things to do recommended for groups

Explore local flavours in Wailea, Kihei with group adventures. Savor the relaxed vibe, stroll beaches, and try native cuisine, all while discovering the island's rich culture and tales of Aloha spirit.

*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

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, ensure you use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Wailea with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Wailea with young kids: Traveling with little ones can be demanding. You have to prioritise their comfort and safety, and ensure there are age-appropriate facilities, like a private swimming pool. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Wailea: For many, a family holiday isn’t complete without the presence of their four-legged companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations supply feeding bowls and beds, ensuring that everyone feels right at home.
  • Planning for a long term stay visiting Wailea: If you're after holiday rentals offering discounts for month-long stays or more, you've come to the right spot. With the proper filter, you can effortlessly find and secure savings on monthly leases. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Wailea

Wailea, Kihei, Hawaii, offers an idyllic escape with stunning beaches like Wailea Beach and Keawakapu Beach, perfect for sunbathing and swimming. Stroll through Wailea Village for unique shops and dining, or explore miles of scenic coastal paths. This neighbourhood embodies a romantic and relaxing atmosphere, making it an ideal destination for couples and families alike. Experience the natural beauty and vibrant culture of Wailea for an unforgettable Maui getaway.

  • Maui: Known for its stunning natural beauty, Maui is an island paradise located approximately 16km from Wailea. Visitors flock to Maui for its pristine beaches and breathtaking scenery, offering a wealth of outdoor activities. Golf enthusiasts can enjoy several renowned golf courses, while shoppers can explore vibrant shopping centres. Local landmarks include beautiful beaches and picturesque bays, making it an ideal spot for family outings or relaxing by the sea.
  • Kihei: Kihei is a charming city where Wailea is situated, making it a convenient base for exploration. This coastal area is celebrated for its excellent beaches and scenic views, attracting travellers looking for outdoor adventures. Kihei offers a variety of activities, including golf and visits to local shopping centres. Notable attractions in the vicinity include lovely beaches, serene bays, and inviting urban parks, perfect for a family day out or a leisurely stroll.
  • South Maui: Just 0.8km from Wailea, South Maui is a delightful region that beckons visitors with its family-friendly experiences and stunning beaches. This area is a hub for shopping, with various shopping centres and malls, as well as top-notch golf facilities. Attractions in South Maui include beautiful beaches, scenic bays, and urban parks, making it an excellent spot for outdoor fun or simply soaking up the sun with loved ones.

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.

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

Booking with Vrbo is simple

Looking to cut costs on your next journey? Being flexible with your travel dates can help, as fares do change over time. Additionally, opting for a longer stay often brings significant savings. To discover the perfect Vrbo property that fits your budget, simply use our filters to sort by price, location, and holiday rental type.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient place to plan new adventures, manage your travel arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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.