Wailea holiday homes

We found 1,407 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Wailea by choosing from 49 houses, 853 flats 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.

  • 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

  • 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

When is the best time to visit Wailea for a holiday rental?
The best time to visit Wailea for a holiday rental is during the peak season from February to April, with March being particularly popular. This period attracts travellers seeking sun-soaked beaches and outdoor adventures, as the weather is pleasantly warm, typically ranging from 20 to 28 degrees Celsius. It's an excellent time for snorkelling, surfing, and exploring the stunning coastal scenery that Wailea is known for.During these months, you'll find a vibrant setting with numerous events and activities taking place, making it ideal for those looking to immerse themselves in the local culture while enjoying the natural beauty of Hawaii. The beaches are inviting, and the lush landscapes provide a great backdrop for relaxation and outdoor exploration.If you're considering a more budget-friendly option, October can be a lovely time to visit Wailea. This month often sees fewer tourists while still offering lovely weather, making it superb for enjoying the beaches and local attractions at a more leisurely pace. You can take advantage of lower rental rates and enjoy a quieter experience without sacrificing the beauty of the island.Ultimately, your choice of when to visit Wailea will depend on whether you prefer the lively option of peak season or the tranquil charm of the shoulder months.
What are the top attractions in Wailea, Hawaii, United States of America?
In Wailea, visitors can enjoy stunning attractions set against a backdrop of natural beauty. The picturesque Wailea Beach is a highlight, offering crystal-clear waters and soft sands, great for sunbathing and swimming. Close by, the luxurious Wailea Golf Club features three world-class courses with breathtaking ocean views, attracting golf enthusiasts from around the globe.For those interested in culture, the nearby Shops at Wailea provide a blend of upscale shopping and dining, with various boutiques and restaurants showcasing local cuisine. Additionally, the scenic Wailea Coastal Walk is a lovely pathway connecting several beaches and resorts, ideal for leisurely strolls and taking in the breathtaking views of the Pacific Ocean.Nature lovers will appreciate the proximity to the lush landscapes of Makena State Park, where you can explore beautiful hiking trails and enjoy the stunning views from Big Beach and Little Beach.
Are all fees included in the Wailea holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wailea holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Wailea with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wailea holiday homes?
You can find great discounts on holiday homes in Wailea on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wailea holiday home booking on Bookabach?
To find Wailea holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Wailea?
A long-stay holiday home in Wailea is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wailea holiday home?
Book your Wailea holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wailea?
Prices for holiday homes in Wailea vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Wailea to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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