Wailea vacation rentals

We found 1,430 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Wailea by choosing from 50 houses, 851 condos, and other vacation rentals. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the amenities you need and want, which might include parking and a fireplace. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Wailea

Showing deals for:Mar 27 - Apr 3

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

Kitchen Area
10 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)

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

Kihei

8% off
Price is $864
$6,050 for 7 nights
All fees included
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

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Find out more about Wailea

Why visit Wailea

  • Beautiful Beaches: Wailea boasts stunning beaches with soft sands and clear waters, perfect for swimming, sunbathing, and water sports.
  • Luxurious Resorts: Experience top-notch accommodations ranging from luxurious resorts to beachfront villas for a relaxing stay.
  • Outdoor Adventures: Enjoy a variety of outdoor activities, including hiking, snorkeling, and golfing in picturesque settings.
  • Cultural Experiences: Immerse yourself in local culture through art galleries, festivals, and traditional Hawaiian events.
  • Scenic Beauty: Marvel at breathtaking landscapes, including sunsets, coastal views, and lush greenery that define Wailea.

Popular types of accommodation around Wailea

Planning a getaway to Wailea? You’re in for a treat. Explore a variety of accommodations, from stunning Wailea condos to luxurious houses and beachfront villas. Whether you're seeking the amenities of Wailea resorts or the comfort of well-appointed apartments, you’ll find the perfect spot to unwind. Discover why Wailea is the ideal destination for your next vacation rental adventure.

  • Condos: The top choice among travelers in Wailea, offering modern amenities and stunning views.
  • Houses: A popular pick for families and groups, providing spacious living and a home-like atmosphere.
  • Apartments: Ideal for solo travelers or couples, these rentals offer convenience and comfort in a compact space.
  • Villas: Luxurious and spacious, perfect for those seeking an upscale getaway with added privacy.
  • Cottages: A charming option for a cozy escape, ideal for a romantic or peaceful retreat.**

Top attractions in and around Wailea

Wailea is the perfect destination for beach lovers and outdoor enthusiasts. Known for its stunning scenery, the area offers a variety of attractions, including beautiful beaches, urban parks, and even a nudist beach. Whether you're traveling with family or friends, you'll find plenty of activities to enjoy and explore in and around Wailea, making it an ideal spot for a memorable vacation experience.

  • Wailea Beach: This stunning beach offers a perfect blend of sun and surf, ideal for relaxation and water activities. With its soft golden sands and clear turquoise waters, it's a picturesque spot for swimming and sunbathing, providing a quintessential Hawaiian beach experience.
  • Makena State Park Beach: Known for its romantic vibes, this nudist beach offers a unique experience surrounded by natural beauty. The expansive shoreline and breathtaking views make it perfect for couples seeking privacy and intimacy.
  • Kamaole Beach Park 3: Located 2 miles from Wailea, this urban park is great for families. It features picnic areas, playgrounds, and easy access to the beach, making it an ideal spot for outdoor fun and relaxation in a vibrant setting.

Things to do recommended for couples

Experience romance in Wailea. Indulge in a rejuvenating treatment at Makena Kai Day Spa, then savor exquisite wines at MauiWine, just 4 miles away, or Tedeschi Vineyards, 5 miles away. Enjoy the perfect blend of relaxation and entertainment in this beautiful Hawaiian paradise.

Things to do recommended for families

Families will love visiting Science City, an exciting arcadeAdventureZone located 12 miles from Wailea. With its family-friendly atmosphere and thrilling activities, it's the perfect spot for fun and adventure together.

Things to do recommended for groups

Explore the Shops at Wailea for a mix of shopping and entertainment, tee off at the Wailea Gold Golf Course for some outdoor fun, and unwind with craft brews at Maui Brewing Co., located 4 miles away, perfect for a relaxed group outing.

*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 traveling with a group, family, or pets, or planning an extended stay, it's important to prioritize your search effectively. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Wailea with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Wailea with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with amenities that suit their age, like a private pool. Additionally, it’s wise to think about how close you are to attractions that are friendly for families.
  • Taking your pets with you to Wailea: For many families, a vacation just isn't the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Wailea: If you're searching for vacation rentals with 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 include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wailea

Wailea is a stunning Hawaiian getaway perfect for beach lovers and outdoor enthusiasts. This picturesque neighborhood offers a romantic and relaxing atmosphere, ideal for couples and families alike. Explore the beautiful Maui beaches, indulge in luxurious resorts, and take part in exciting excursions. Don't miss out on the vibrant local culture and breathtaking scenery that make a Wailea vacation truly unforgettable.

  • Maui: As one of the most breathtaking islands in Hawaii, Maui is located approximately 10 miles from Wailea. Visitors flock to this tropical paradise for its stunning outdoor scenery and pristine beaches. Whether you're teeing off at one of its renowned golf courses or exploring the local shopping centers, there's plenty to do. Maui also boasts beautiful beaches, serene bays, and urban parks that provide a perfect backdrop for relaxation and adventure. Don’t miss the chance to indulge in water sports like snorkeling and surfing, or simply enjoy a sunset view from the shore.
  • Kihei: Kihei is a vibrant city and the immediate neighbor of Wailea, known for its family-friendly atmosphere and beautiful beaches. This coastal city offers an array of outdoor activities, from golfing to beach outings. With a variety of shopping centers and urban parks, Kihei is the perfect spot for families to enjoy quality time together. Explore the sandy shores, visit the local playgrounds, or take part in beach activities that make this city a favorite among locals and tourists alike. Kihei truly embodies the laid-back Hawaiian lifestyle.
  • South Maui: Situated just half a mile from Wailea, South Maui is a paradise for beach lovers and outdoor enthusiasts. This area is renowned for its family-friendly beaches and vibrant parks, making it an ideal destination for visitors of all ages. South Maui offers plenty of opportunities for golf and shopping, all while being close to stunning bays and scenic landscapes. Whether you're looking to relax on the beach or embark on outdoor adventures, South Maui promises an unforgettable experience filled with the beauty of Hawaii.

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 hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the organizer definitely has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member savings and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly area where you can easily plan new trips, continue from where you last stopped, or manage and review your travel arrangements. You can find your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Paradise at Wailea vacation home rentals

Legend has is it that Wailea, ‘The Waters of Lea’, got its name when a goddess took the shape of a beautiful bird and flew over its magnificent shoreline. In World War 2 US Marines prepared for battle at Wailea, but now it's among Maui’s most tranquil beach resorts. Visitors can enjoy more than 1,500 acres of lush tropical gardens and parkland, 2 miles of sun-kissed beach, and captivating views of the Pacific Ocean. Make the most of Wailea’s serene setting and book a Wailea vacation rental to be near the picturesque beaches, ocean views and many other attractions.

Attractions near Wailea vacation rentals

Among Wailea's more elusive residents are Spinner Dolphins. These beautiful creatures are best glimpsed at Le Perouse Bay, a lava-shaped bay and one end of Maui's historic King's Trail. As the day draws to a close, head to scenic Keawakapu Beach and stake out a good spot to catch Maui's world-famous sunset. And if you want the complete Hawaiian experience, then check out the Grand Luau at Honua'ula. There you'll be treated to spectacular fire performers, Hula dancers, and a mouth-watering all-you-can-eat buffet, so you might want to let your belt out a notch or two!

Things to do near Wailea vacation homes

The sun shines year round in Wailea, so there's never a bad time to head down to Wailea Beach. Voted 'America's best beach' in 1999, it's the area's most popular spot to catch some rays, ride some waves or just frolic in the water. If it's some adventure you're after, then saddle up at Ulupalakua Ranch. Guided horseback tours wind through Maui's lush interior, and along its majestic shore, and cater to riders of all abilities. If golf's more your thing, then you'll not be disappointed either, as Wailea has 3 18-hole courses.

Local weather for your stay in Wailea vacation homes

Whatever else you do, pack sunscreen. Wailea's tropical climate means it's warm and sunny all year round. While July and August are the hottest months with temperatures soaring into the high 80s, all the other months of the year experience average highs in excess of 80 F. Rain showers are common, particularly in December and January, although they tend to short and light, and while it can be humid in Wailea, it's not as stifling as it can be in other tropical climes. With such pleasant year-round weather, there's never a bad time to book a Wailea vacation rental.

Best beaches near Wailea vacation homes

Wailea has gorgeous beaches suited to different activities and adventures. Vacation homes are available near places like Makena Alanui, a tranquil beach with clear waters for snorkeling and a native population of sea turtles, and Polo Beach Park, a white-sand beach with a natural backdrop and trails. You'll also like Molokini, a crescent islet with vibrant marine life to explore with snorkeling.

Couple's retreat near Wailea vacation rentals

The idyllic surrounds and fun-filled activities of Wailea make it ideal for a couple’s getaway. Vacation homes are available near places like Maui Tropical Plantation, a working farm with tours of sugarcane and pineapple fields, and Ali’I Kula Lavender, a sprawling lavender farm with tours and a gift shop with products. You'll also enjoy Ahihi-Kinau Natural Area Reserve, a protected coastal lava field with diverse wildlife, sandy beaches, and turquoise waters popular for diving and snorkeling.

Frequently asked questions

What is the most popular type of vacation rental in Wailea?
In Wailea, condos are the most popular type of vacation rental, with about 935 available throughout the area. These condos are typically located near stunning beaches and the Wailea Beach Path, offering easy access to the ocean and stunning sunset views. Most rooms come equipped with modern amenities, including fully equipped kitchens, spacious living areas, and luxurious outdoor spaces like balconies or patios for enjoying the tropical climate.

For those seeking more spacious rooms, there are roughly 71 villas and 48 vacation houses available, ideal for families or larger groups. These properties often feature multiple bedrooms, private pools, and expansive outdoor entertaining areas, allowing guests to relax and enjoy the beautiful surroundings.
Are there any beach house rentals in Wailea?
In Wailea, Hawaii, there are approximately 1,690 beach house rentals available, making it a prime destination for travelers seeking coastal accommodations. These beach houses are often located in scenic neighborhoods close to popular points of interest such as Wailea Beach, the Shops at Wailea, and the stunning Wailea Golf Club. Travelers can expect a variety of amenities, including spacious layouts with multiple bedrooms, fully equipped kitchens, private pools, and outdoor decks with ocean views. Find your rental near the beach in Wailea.
How much does it cost to rent a vacation home in Wailea?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Wailea?
In Wailea, popular vacation rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy the convenience of home. Many rentals also feature access to shared pools, great for relaxing and soaking up the sun after a day at the nearby beaches. Additional amenities often include blenders for making refreshing smoothies or cocktails, and coffee or tea makers to start the day off right.
Are there any family house rentals in Wailea?
In Wailea, Hawaii, there are numerous family-friendly house rentals available—around 830 options to choose from. This beautiful area is known for its stunning beaches and luxurious resorts, making it an ideal destination for families. Many of these homes feature spacious layouts, full kitchens superb for meal preparation, and outdoor spaces where children can play or where families can enjoy al fresco dining.

Visitors will appreciate amenities such as private pools, laundry facilities, and air conditioning, ensuring a comfortable stay. Wailea's proximity to attractions like the Wailea Beach Path and the Shops at Wailea adds to its appeal, providing opportunities for beach activities and shopping. With easy access to golf courses and scenic parks, travelers will find plenty to keep the whole family entertained. See all family-friendly rentals in Wailea.
Can I rent a vacation home with a pool or hot tub in Wailea?
In Wailea, there are plenty of vacation homes available for rent that come with pools and hot tubs, with approximately 1,053 options featuring pools and around 569 offering hot tubs. This upscale neighborhood on the island of Maui is known for its luxurious feel and stunning ocean views, making it a sought-after destination for travelers.

Many properties in Wailea boast a range of amenities, including private swimming pools, relaxing hot tubs, spacious outdoor patios, and well-equipped kitchens superb for entertaining. Guests can also look forward to lush tropical landscaping, outdoor dining areas, and sometimes even direct access to pristine beaches.

Wailea is also home to several world-class golf courses and upscale shopping, providing a superb blend of relaxation and leisure activities. Find your rental in Wailea with a pool or a hot tub.
Are there any Wailea vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Wailea with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Wailea?
Yes, you can book pet-friendly vacation rentals in Wailea, where a variety of options are available. This beautiful area in Maui is known for its stunning beaches, upscale resorts, and lush landscapes. Many vacation rentals in Wailea come equipped with amenities such as private pools, spacious patios, and fully equipped kitchens, making them ideal for families or groups looking for both comfort and convenience.

The neighborhood offers easy access to several pet-friendly points of interest, including the picturesque Wailea Beach, which is great for leisurely strolls with your furry friend. Additionally, nearby parks and scenic walking trails provide opportunities for outdoor activities and exploration. Some rentals may even feature outdoor spaces designed for pets, ensuring a welcoming environment for your four-legged companions. See all pet-friendly rentals in Wailea.
Can I find long-stay vacation rentals in Wailea?
A long-stay vacation rental in Wailea is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Wailea for a vacation rental?
The best time to visit Wailea for a vacation rental is during the peak season from February to April, with March being particularly popular among travelers. This timeframe draws visitors eager to bask in the sunny weather and enjoy the stunning beaches, lush landscapes, and vibrant local culture that Wailea offers.

During these months, you can expect warm temperatures averaging in the low to mid-80s Fahrenheit. This climate is ideal for outdoor activities such as snorkeling, swimming, and exploring the scenic coastline. The pleasant weather also allows for convenient sightseeing, with nearby attractions like the scenic Road to Hana and Haleakalā National Park easily accessible.

If you're looking for a more budget-friendly option, consider visiting in October. This month often features fewer crowds, allowing for a more relaxed experience while still enjoying beautiful weather.
Are there any remote work vacation rentals in Wailea?
In Wailea, Hawaii, there is a robust selection of remote work vacation rentals, with approximately 1,045 options available for travelers. This beautiful area is known for its stunning beaches, upscale resorts, and vibrant local culture, making it an ideal place for those looking to blend work and leisure. Many of the vacation rentals feature dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable environment for productivity. High-speed Wi-Fi is commonly available, along with other amenities such as laptop workspaces and safe storage for valuables.

Travelers can enjoy the breathtaking landscapes and outdoor activities Wailea has to offer, including nearby golf courses and hiking trails along the coastline. Additionally, the area is home to luxury shopping and exquisite dining options, providing an enriching experience after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Wailea vacation rental?
Book your Wailea vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Wailea?
In Wailea, visitors can enjoy stunning beaches and luxury resorts, with the Wailea Beach being a highlight for sunbathing and water activities. The area is known for its upscale shopping and dining at the Shops at Wailea, where travelers can find a variety of boutiques and restaurants. For natural beauty, the nearby Makena State Park offers picturesque landscapes and opportunities for snorkeling at Big Beach. Golf enthusiasts can explore several world-class golf courses located in the region, providing breathtaking ocean views.
Can I change or cancel my Wailea home rental booking on Vrbo?
To find Wailea vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wailea vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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