Wailea vacation rentals

We found 1,432 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

10% off
Price is CA $983
CA $9,539 total
includes taxes & fees
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

  • Stunning Beaches: Wailea boasts beautiful beaches like Ulua Beach and Wailea Beach, perfect for sunbathing and swimming.
  • Outdoor Adventures: Explore scenic hiking trails and engage in exciting water sports for a thrilling experience.
  • World-Class Golf: The Wailea Golf Club offers fantastic golfing opportunities with breathtaking ocean views.
  • Family-Friendly Activities: Enjoy a variety of family-oriented experiences, ensuring fun for all ages.
  • Diverse Accommodation: Choose from luxurious resorts, private vacation homes, and cozy condos for a perfect stay.

Popular types of accommodation around Wailea

If you're curious about the types of accommodations available in Wailea, you're in for a treat. Our most popular options include stunning condos, houses, and cozy apartments, perfect for your getaway. Whether you're looking for a Wailea resort experience or the comfort of a Wailea vacation rental, we've got you covered with transparent information and great savings to ensure a memorable stay.

  • Condos: The top choice for vacation rentals in Wailea, offering comfortable amenities and stunning ocean views for a perfect getaway.
  • Houses: Ideal for families or groups, these homes provide spacious living areas and a sense of privacy during your stay.
  • Apartments: A convenient option for couples or solo travellers seeking a home-like atmosphere with easy access to local attractions.
  • Villas: Luxurious spaces that combine elegance and relaxation, perfect for an upscale experience in Wailea.
  • Cottages: Quaint and charming, these cozy retreats offer a serene escape amidst the beauty of Hawaii.**

Top attractions in and around Wailea

Wailea, nestled in Kihei, Hawaii, is perfect for those seeking beach, outdoor, and scenic vacations. With attractions like Ulua Beach, Wailea Beach Walk, and the Wailea Golf Club, there's something for everyone. Families can enjoy a variety of experiences, including the stunning Wailea Beach and exciting Maui adventures. Whether you're a solo traveller or with loved ones, Wailea offers a delightful blend of relaxation and adventure.

  • Wailea Beach: Known for its stunning sunsets and soft sands, Wailea Beach offers a perfect spot for relaxation and water activities, embodying the quintessential Hawaiian beach vibes.
  • Makena State Park Beach: This secluded nudist beach is ideal for couples seeking romance, featuring breathtaking views and a serene atmosphere, perfect for unwinding together.
  • Kamaole Beach Park 3: Located 3.2km from Wailea, this urban park is great for families, providing ample space for picnics and outdoor activities amidst the vibrant city vibes.

Things to do recommended for couples

For a romantic getaway in Wailea, indulge in a rejuvenating treatment at Makena Kai Day Spa. Then, experience the charm of MauiWine and Tedeschi Vineyards, both a short drive away, where you can sip delightful wines and soak in the enchanting ambiance together.

Things to do recommended for families

Experience the excitement of Science City, an arcadeAdventureZone located 19.3km from Wailea. This family-friendly destination offers thrilling activities suitable for all ages, ensuring memorable moments for everyone in the family.

Things to do recommended for groups

Groups visiting Wailea can enjoy shopping at the Shops at Wailea, tee off at the Wailea Gold Golf Course, and unwind with craft brews at Maui Brewing Co., located a short drive away. These experiences offer a blend of relaxation, entertainment, and outdoor fun.

*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 planning a trip with friends, family, pets, or seeking extended stays, be sure to use the appropriate filters to prioritize your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Wailea with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group activities. Thankfully, you can easily refine your search to include these options and more on Vrbo.
  • Traveling to Wailea with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities, like a private pool. Additionally, considering your closeness to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to Wailea: For many, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most 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 in search of vacation rentals that offer 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 features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Wailea

Wailea, located in Maui, offers a stunning blend of beachside relaxation and outdoor adventures, perfect for a Hawaiian holiday. This vibrant neighbourhood is ideal for romantic getaways and family-friendly excursions alike. Explore the breathtaking scenery, indulge in local cuisine, and soak in the sun at pristine beaches. Whether seeking tranquil moments or exciting activities, Wailea promises an unforgettable island getaway for every traveller.

  • Maui: Maui is a stunning island located approximately 16.1km from Wailea, renowned for its breathtaking outdoor scenery. Visitors are drawn to Maui for its mesmerizing beaches and vibrant landscapes, ideal for a variety of outdoor activities. You can enjoy a round of golf at one of the many exquisite golf courses, indulge in shopping at local centres, or simply take in the beautiful views at urban parks. Key attractions include pristine beaches and picturesque bays, making Maui a perfect destination for those seeking adventure and relaxation.
  • Kihei: Sitting adjacent to Wailea, Kihei is a charming city that embodies the spirit of Hawaiian beach life. Visitors flock to Kihei for family-friendly outdoor experiences, including its stunning beaches and urban parks. The area offers ample opportunities for golf enthusiasts and shopping aficionados alike. Local landmarks feature family beaches that provide a safe and enjoyable environment for all ages, making Kihei a great spot for both relaxation and recreation.
  • South Maui: Located a mere 805m from Wailea, South Maui is a vibrant area that attracts visitors with its inviting beaches and family-oriented atmosphere. This region offers a plethora of activities, from golfing to shopping, ensuring a fulfilling experience for every traveler. With its beautiful beaches, urban parks, and scenic bays, South Maui promises a delightful exploration for those looking to soak in the sun and enjoy quality time 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. 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 some money on your next adventure? Being flexible with your travel dates can really make a difference, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits 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 best options for your Canadian getaway.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, refine your existing travel arrangements, or manage your bookings with ease. All of the properties you’ve saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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 approximately 951 available throughout the area. These condos are typically located in upscale, beachfront complexes, offering stunning ocean views and easy access to the beautiful Wailea Beach. Most rooms come equipped with modern amenities, including fully fitted kitchens, spacious living areas, and private balconies, 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 rentals available, making it a popular destination for those seeking a coastal getaway. These beach houses are situated in picturesque neighbourhoods close to stunning beaches like Wailea Beach and Makena Beach, as well as the scenic Wailea Coastal Walk. 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 travelling 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.
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.
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 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 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. 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 vacation rental?
March is the most popular month to visit Wailea, Hawaii, as it falls within the peak season from February to April. This period is especially appealing to travellers seeking sun-soaked beaches and vibrant outdoor activities. With the gentle trade winds and average temperatures ranging from 22 to 28 degrees Celsius, the weather is great for exploring the stunning coastline, diving in crystal-clear waters, or simply relaxing under the warm Hawaiian sun.

During this peak season, you can expect a lively atmosphere, with plenty of opportunities for water sports, hiking along scenic trails, and enjoying the local culture at various festivals and events. The stunning beaches of Wailea, including the famous Wailea Beach, create an idyllic backdrop for outdoor adventures and sightseeing.

For those looking for a more budget-conscious option, consider visiting in October. This month offers a quieter experience, with fewer crowds while still retaining the beauty of Wailea. You'll have the chance to enjoy the warm weather and tranquil beaches without the hustle and bustle of peak season.
Are there any remote work vacation rentals in Wailea?
In Wailea, Hawaii, there are a substantial number of remote work vacation rentals available—approximately 1,077 properties suiting those looking to blend work and leisure. This picturesque area is known for its stunning beaches, luxury resorts, and vibrant ocean views, making it an ideal location for a working vacation.

Travellers can expect a range of amenities designed for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, and ergonomic chairs. Many rentals also feature additional conveniences such as computer monitors and safe storage options, ensuring a productive environment. 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.
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 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 cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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