Wailea holiday lettings

We found 1,427 holiday rentals — enter your dates for availability

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

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

Living area
10 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)

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

Kihei, HI

15% off
Price is £4,140
for 7 nights, 1 apartment
£591 per night
includes taxes & fees
Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

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Why visit Wailea

  • Stunning Beaches: Enjoy the sun on Wailea Beach, known for its golden sands and crystal-clear waters, perfect for relaxation and water sports.
  • Picturesque Boardwalk: Stroll along the scenic Wailea Boardwalk, offering breathtaking views and a family-friendly atmosphere.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking to snorkelling, set against Wailea's stunning natural backdrop.
  • Charming Neighbourhoods: Explore nearby towns, each with its unique charm, enhancing your Hawaiian experience.
  • Diverse Accommodation: Choose from an array of holiday rentals, from condos to luxurious resorts, catering to all tastes and budgets.

Popular types of accommodation around Wailea

At Vrbo, we offer a variety of accommodation options in Wailea, perfect for British travellers seeking sun-soaked relaxation. Popular choices include condos, houses, and apartments, catering to all preferences and budgets. Whether you're looking for Wailea hotels or luxurious resorts, our selection of Wailea vacation rentals ensures you find the ideal home away from home for your Hawaiian getaway.

  • Condos: The top choice for holidaymakers in Wailea, offering modern amenities and stunning views.
  • Houses: A fantastic option for families or groups seeking space and comfort during their stay.
  • Apartments: A practical selection for those wanting a self-catering experience in a vibrant area.
  • Villas: Elegant and spacious, perfect for a luxurious getaway with private facilities.
  • Cottages: Quaint and charming, ideal for a peaceful retreat close to nature.**

Top attractions in and around Wailea

Wailea offers a delightful blend of beach and outdoor activities, making it an ideal destination for a scenic holiday. Visitors can explore stunning attractions like Wailea Beach and the picturesque Wailea Boardwalk, perfect for families and outdoor enthusiasts alike. With its beautiful beaches and urban parks, Wailea promises a memorable experience for all who seek relaxation and adventure in this captivating Hawaiian locale.

  • Wailea Beach: This stunning beach offers soft sands and crystal-clear waters, perfect for sunbathing and swimming. The tranquil atmosphere enhances its beach vibes, making it an ideal spot for relaxation and leisure.
  • Makena State Park Beach: Known for its romantic vibes, this nudist beach offers seclusion and breathtaking views. It's a perfect getaway for couples seeking intimacy amidst natural beauty.
  • Kamaole Beach Park 3: Located 1.2km away from Wailea, this urban park features family-friendly amenities and scenic picnic spots, making it ideal for outdoor gatherings in a lively city setting.

Things to do recommended for couples

For a romantic getaway in Wailea, indulge in a relaxing treatment at Makena Kai Day Spa. Enjoy a delightful wine tasting at MauiWine, just 2.5km away, or visit Tedeschi Vineyards, 3.1km from Wailea, for a charming experience filled with romance and entertainment.

Things to do recommended for families

Families will delight in the excitement of Science City, an arcade adventure zone located 7.5km from Wailea. This vibrant venue offers a fantastic atmosphere for fun and adventure, ensuring a memorable experience for all ages.

Things to do recommended for groups

Groups visiting Wailea can enjoy a shopping spree at the Shops at Wailea, play a round at the scenic Wailea Gold Golf Course, or indulge in craft brews at Maui Brewing Co., located a mere 2.5km away, perfect for a memorable day out.

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

If you’re travelling with a group, as a family, with your pets, or seeking longer stays, it’s important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Wailea with a group: Think about how many bedrooms you require, as well as any amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and much more on Vrbo.
  • Traveling to Wailea with young kids: Traveling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you may want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wailea: For many families, a holiday wouldn’t be the same without their beloved pet by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Wailea

Wailea, a stunning neighbourhood in South Maui, offers a delightful blend of romantic beaches and outdoor adventures, making it an ideal spot for a family vacation. With its picturesque scenery and relaxing atmosphere, visitors can explore the enchanting Hawaiian Islands and enjoy various excursions. Nearby towns add to the charm, providing a perfect escape for those seeking both tranquility and excitement during their stay in this beautiful part of Hawaii.

  • Maui: Maui, a stunning island located approximately 6.2km from Wailea, is renowned for its breathtaking scenery and outdoor activities. Visitors flock to Maui to soak up the sun on its pristine beaches, explore lush landscapes, and enjoy thrilling adventures. The island boasts excellent golf courses, ideal for enthusiasts looking to tee off against a backdrop of stunning views. Shopping centres are scattered throughout, offering a variety of local and international goods. Key attractions include idyllic beaches, tranquil bays, and urban parks that provide a perfect setting for relaxation and exploration.
  • Kihei: Just 3.7km from Wailea, Kihei is a vibrant city popular with families and outdoor enthusiasts. With its beautiful beaches and welcoming atmosphere, Kihei offers a plethora of activities for all ages. Visitors can enjoy beach days, participate in water sports, or explore the nearby parks. Golf courses and shopping centres are easily accessible, making it convenient for those seeking leisure and retail therapy. Local highlights include family-friendly beaches and urban parks, perfect for picnicking or a leisurely stroll.
  • South Maui: Located a mere 311m from Wailea, South Maui is a picturesque area that captures the essence of Hawaiian beauty. Known for its stunning beaches and outdoor activities, it is an ideal destination for families and those looking to connect with nature. South Maui offers a range of popular golf courses and shopping centres, ensuring visitors have everything they need for a wonderful stay. Attractions include pristine beaches, scenic urban parks, and stunning bays, all inviting exploration and relaxation.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 Vrbo is simple

Are you keen to make the most of your travel budget? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, consider booking a longer stay, which can result in substantial discounts. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for you to plan new trips, resume your previous arrangements, or manage your travel itinerary. You'll discover your saved or booked properties neatly organised into categories: Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Wailea?
In Wailea, condos are the most popular type of holiday rental, with around 951 available in the area. These condos are typically located in luxurious beachfront complexes, offering stunning ocean views and easy access to the beautiful Wailea beaches. Most rooms come equipped with full kitchens, spacious living areas, and private lanais, allowing guests to enjoy the tropical surroundings.
Are there any beach house rentals in Wailea?
In Wailea, Hawaii, there are approximately 1,606 beach house holiday rentals available, making it a popular destination for those seeking a coastal escape. These rentals are primarily situated near stunning locations such as Wailea Beach, Makena State Park, and the luxurious resorts that dot the coastline. Visitors can expect a range of amenities, with most beach houses featuring spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, such as pools or patios, ideal for enjoying the warm Hawaiian climate. Many properties also offer breathtaking ocean views and direct access to the beach, enhancing the overall holiday experience. Find your rental near the beach in Wailea.
How much does it cost to rent a holiday home in Wailea?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wailea to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wailea holiday house rentals?
You can find great discounts on house rentals in Wailea on Vrbo, 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.
Are there any Wailea holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Wailea?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Wailea for a holiday rental?
The most popular time to visit Wailea for a holiday rental is during the peak season from February to April. This period is ideal for sun-seeking travellers who wish to bask in the warm Hawaiian sunshine while enjoying the pristine beaches and stunning ocean views. With temperatures averaging around 25-28°C, outdoor enthusiasts can delight in a range of activities, from snorkelling in crystal-clear waters to hiking scenic coastal trails.

March, in particular, stands out as a favourite month among visitors, as it offers a vibrant atmosphere with a plethora of events and cultural festivals. The pleasant weather encourages guests to explore Wailea's luxurious resorts and indulge in the many fine dining options available, ensuring a memorable stay.

For those looking for a more budget-friendly option, consider visiting in October. This month brings a quieter vibe, superb for travellers seeking relaxation without the bustling crowds. October often features pleasant weather as well, with temperatures still hovering in the low 27°C range, allowing for enjoyable beach days and leisurely strolls through Wailea's stunning landscapes.
Are there any remote work holiday rentals in Wailea?
In Wailea, Hawaii, there is an impressive selection of remote work holiday rentals, with around 1,077 options available. This beautiful coastal area is renowned for its stunning beaches, upscale resorts, and vibrant local culture, making it an attractive destination for those looking to blend work and leisure. Many of the properties designed for remote work come equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, ergonomic chairs, and sometimes even meeting rooms, ensuring a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wailea holiday rental?
Book your Wailea holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Wailea home rental booking on Vrbo?
To find Wailea holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Wailea holiday rental prices shown on Vrbo?
Vrbo 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.

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