Wailea vacation rentals

We found 1,423 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Wailea by choosing from 49 houses, 854 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:Jun 5 - Jun 12

Image gallery for LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B

This is our beach entry stairwell down to the beach. Need an access code.
9.8 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)

LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B

Kihei

8% off
Price is $522
$3,657 for 7 nights
All fees included
LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B

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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 vacation rental option, with about 983 available across this beautiful coastal area. Many of these condos are situated in prime locations near the stunning beaches and world-class golf courses, offering breathtaking ocean views. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and access to resort-style pools and fitness facilities.

For those seeking more space, around 77 villas are available, typically featuring luxurious amenities like private pools, outdoor dining areas, and expansive terraces to enjoy the tropical climate. Additionally, approximately 48 vacation houses are scattered throughout Wailea, often providing multiple bedrooms, private gardens, and easy access to local attractions.
Are there any beach house rentals in Wailea?
In Wailea, there are approximately 1,841 beach house rentals available, making it a popular destination for travelers seeking a coastal getaway. These rentals vary greatly in size and style, suiting different preferences and group sizes. Many of the beach houses come equipped with modern amenities such as fully stocked kitchens, spacious living areas, private pools, and outdoor spaces great for enjoying the stunning Hawaiian sunsets. Additionally, many properties provide easy access to beautiful beaches and nearby attractions, including the Wailea Beach Path and luxury shopping at The Shops at 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 rentals offer a range of amenities that cater to travelers looking for comfort and convenience. Many rentals come equipped with fully functional kitchens, allowing guests to prepare their own meals with ease. Outdoor spaces like decks or patios are common, providing a great setting for enjoying the beautiful Hawaiian weather. Onsite parking is also a typical feature, making it convenient for those who wish to explore the area by car. Additionally, many properties include coffee and tea makers for that morning boost, and shared pools are prevalent, offering a refreshing spot to relax and socialize.
Can I find family house rentals in Wailea?
In Wailea, Hawaii, there are numerous family-friendly house rentals available—around 794 to choose from. This beautiful area is known for its stunning beaches, luxurious resorts, and outdoor activities, making it an ideal destination for families. Many of these homes boast spacious living areas, fully equipped kitchens great for preparing meals together, and outdoor spaces where children can play or families can gather for barbecues.

Amenities often include private pools, hot tubs, and laundry facilities, ensuring a comfortable stay for all. Families can also enjoy proximity to local attractions, such as the Wailea Beach Path, which offers scenic views and access to some of the best beaches in Maui. Nearby, you'll find shops, dining options, and activities like snorkeling and whale watching, suiting both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Wailea?
In Wailea, Hawaii, there are plenty of vacation homes available for rent that feature both pools and hot tubs, with around 1,064 options offering pools and 704 providing hot tubs. This beautiful area is known for its luxurious beachfront properties and stunning ocean views, primarily located in neighborhoods like Wailea Beach and Makena.

Travelers can expect a range of amenities in these rentals, including private infinity pools, spacious outdoor decks for sunbathing, and hot tubs superb for relaxation after a day of exploring. Many homes also come equipped with modern kitchens, air conditioning, and comfortable living spaces, making them ideal for families or groups seeking a tropical getaway.
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.
Can I book pet-friendly vacation rentals in Wailea?
In Wailea, travelers can find a variety of pet-friendly vacation rentals, with around 14 options available. This beautiful area is known for its stunning beaches, upscale resorts, and gorgeous ocean views. Many of the vacation rentals here offer amenities such as private pools, outdoor patios, and fully equipped kitchens, making them great for families or groups looking for a comfortable stay.

Wailea is also home to several pet-friendly points of interest, including the scenic Wailea Coastal Path, which provides a wonderful opportunity for walks with pets while enjoying breathtaking ocean vistas. Additionally, local parks, like the nearby Kihei Community Park, offer green spaces for pets to play.
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 book a vacation rental in Wailea is during the peak season from February to April, when travelers flock to this stunning Hawaiian destination to soak up the sun and enjoy the vibrant local culture. March, in particular, stands out as a popular month, offering visitors idyllic weather and a plethora of outdoor activities, superb for those looking to relax on pristine beaches or explore the lush landscape.

During this peak period, temperatures typically range from the mid-70s to low 80s Fahrenheit, creating a comfortable atmosphere for sunbathing, snorkeling, and hiking the scenic trails in the area. The beautiful beaches and picturesque views make Wailea an ideal spot for families and couples seeking both adventure and relaxation.

If you're looking for a more budget-friendly option, consider visiting Wailea in October. While this month is outside the high tourist season, it still boasts pleasant weather and fewer crowds, allowing for a more tranquil experience. October offers opportunities for enjoying the stunning sunsets and exploring the local dining scene without the hustle and bustle of peak season.

Ultimately, the best time to visit Wailea depends on your preferences—whether you want to immerse yourself in a lively option filled with activities or prefer a quieter getaway to enjoy the natural beauty of Hawaii.
Are there any remote work vacation rentals in Wailea?
In Wailea, Hawaii, there are ample remote work vacation rentals available, with around 1,118 options to choose from. This beautiful area is known for its stunning beaches, upscale resorts, and lush landscapes, making it an idyllic setting for those looking to combine work and leisure. Many of the rentals feature essential remote work amenities such as free Wi-Fi, providing reliable internet access to facilitate productivity.

Travelers can expect a variety of accommodations ranging from luxurious condos to spacious homes, often equipped with comfortable workspaces, views of the ocean, and access to resort-style amenities such as pools and fitness centers. Additionally, the proximity to beautiful beaches like Wailea Beach and Makena Beach offers excellent opportunities for relaxation 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, Hawaii, United States of America?
Wailea is known for its stunning beaches and luxurious resorts, making it a prime destination for travelers. One of the top attractions is Wailea Beach, a beautiful stretch of golden sand great for sunbathing and swimming. Nearby, the Wailea Beach Path offers scenic views along the coastline and connects several beaches and resorts, making it ideal for leisurely strolls or jogging.

Another highlight is the Shops at Wailea, an upscale shopping center featuring a variety of boutiques, art galleries, and dining options, where visitors can enjoy both shopping and gourmet meals. For those interested in golf, the Wailea Golf Club boasts three championship courses with breathtaking ocean views, attracting golf enthusiasts from around the world.

Additionally, the area is close to the stunning Makena State Park, which offers access to some of Maui's most pristine beaches. Travelers can also explore the nearby Molokini Crater, a famous snorkeling destination, easily accessible by boat tours departing from Wailea.
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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