Vacation rentals near Wailea Beach

We found 4,847 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals within easy reach of Wailea Beach that provide the perfect home base for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include parking and a fireplace. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Wailea Beach

Showing deals for:Jul 24 - Jul 31

Image gallery for Privacy in Paradise! 2nd Flr, updated,across from Beach! Smaller 6 unit complex

Hale Wailana Resort building
8.6 out of 10, Excellent, (91 reviews)
Excellent
(91 reviews)

Privacy in Paradise! 2nd Flr, updated,across from Beach! Smaller 6 unit complex

Kihei

10% off
Price is $277
$1,939 for 7 nights
All fees included
Privacy in Paradise! 2nd Flr, updated,across from Beach! Smaller 6 unit complex

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Find out more about Wailea Beach

Why visit Wailea Beach

  • Stunning Beaches: Enjoy the beautiful sands and crystal-clear waters of Wailea Beach, perfect for sunbathing and swimming.
  • Luxurious Accommodations: Choose from upscale resorts and cozy vacation rentals that offer breathtaking views and amenities.
  • Outdoor Adventures: Engage in various activities like snorkeling, hiking, and exploring local parks, ensuring fun for all ages.
  • Charming Wailea Village: Discover local shops, dining options, and a vibrant atmosphere that enhances your Hawaiian experience.
  • Family-Friendly Excursions: Enjoy a range of activities suitable for families, making it a perfect destination for everyone.

Popular types of accommodation around Wailea Beach

Discover the perfect getaway with our vacation rentals in Wailea Beach. Whether you're seeking a cozy condo, a spacious private vacation home, or a modern apartment, we have options to suit every traveler. Wailea Beach Resort offers stunning views and luxurious amenities, making it a top choice for visitors to Maui. Explore your ideal Wailea condo or resort today and experience the beauty of Wailea Beach firsthand.

  • Condos: The top choice for visitors, offering convenient amenities and stunning views, perfect for a relaxing getaway in Wailea Beach.
  • Houses: Ideal for families or groups seeking spacious accommodations with a home-like atmosphere.
  • Apartments: A great option for those looking for a cozy place with essential amenities, close to the beach.
  • Villas: Luxurious and spacious, these rentals provide an upscale vacation experience with private settings.
  • Cottages: Charming and quaint, these options offer a more intimate atmosphere for a peaceful retreat.**

Top attractions near Wailea Beach

Wailea Beach in Kihei, Hawaii, offers a delightful mix of attractions for beach lovers and outdoor enthusiasts. Visitors can enjoy the sun at the beautiful beach, explore local urban parks, or even visit nearby nudist beaches. Whether you're traveling with family or seeking adventure, Wailea Beach provides a perfect setting for a memorable vacation filled with relaxation and fun activities.

  • Kamaole Beach Park: A beautiful beach offering classic Hawaiian vibes, perfect for sunbathing, swimming, and beach volleyball. Its soft sands and clear waters provide a relaxing atmosphere for visitors looking to soak up the sun.
  • Kamaole Beach Park 3: A family-friendly urban park with spacious green areas, picnic spots, and outdoor activities. This park combines city vibes with a tranquil environment, making it ideal for families to enjoy a day out.
  • Makena State Park Beach: A secluded nudist beach that exudes romance and intimacy. With stunning views and a serene atmosphere, it’s a perfect spot for couples looking to connect with nature and each other.

Things to do recommended for couples

For a romantic getaway in Wailea Beach, indulge in relaxation at Makena Kai Day Spa, just 2 miles away. Enjoy a delightful wine tasting at MauiWine, 4 miles away, or visit Tedeschi Vineyards, 5 miles away, for a charming atmosphere filled with love and entertainment.

Things to do recommended for families

Families visiting Wailea Beach can experience the excitement of Science City, an arcade adventure zone located 12 miles away. This vibrant spot offers a variety of fun activities perfect for kids, ensuring a memorable day filled with family-friendly entertainment.

Things to do recommended for groups

Groups visiting Wailea Beach can enjoy shopping at the Shops at Wailea, just 0.4 miles away, play a round at Wailea Blue Golf Course, 0.6 miles away, or savor craft brews at Maui Brewing Co., located 5 miles from the beach, perfect for fun and relaxation.

*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 Beach

When traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wailea Beach with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Wailea Beach with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, considering your location relative to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Wailea Beach: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea Beach: If you're in search of vacation rentals offering discounts for month-long stays, 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 parking, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Wailea Beach

Wailea Beach offers a perfect blend of romance and relaxation, making it an ideal destination for your Maui getaway. Explore the charming Wailea Village, indulge in family-friendly excursions, and bask in the sun at stunning Maui beaches. This vibrant area is known for its luxurious atmosphere, where you can enjoy both tranquil moments and exciting adventures. Whether you're seeking a romantic escape or a family vacation, Wailea Beach has something for everyone.

  • Maui: Maui is a stunning island located 11 miles from Wailea Beach, renowned for its breathtaking outdoor experiences and pristine beaches. Visitors flock to Maui for its picturesque scenery, where you can indulge in activities such as golfing at world-class courses, shopping at local centers, and exploring beautiful coastal bays. The island is also home to a variety of urban parks perfect for picnics and leisurely strolls, making it an ideal escape for nature lovers and adventure seekers alike.
  • Kihei: Kihei is the vibrant city that houses Wailea Beach, offering visitors an inviting atmosphere filled with family-friendly activities. Known for its gorgeous beaches and outdoor adventures, Kihei is perfect for families looking to enjoy sun-soaked days. Popular attractions include local golf courses and shopping centers that cater to various tastes. With its scenic beachfront parks and family-friendly beaches, Kihei ensures a memorable experience for all ages.
  • Wailea: Wailea is an upscale neighborhood that encompasses the famous Wailea Beach, attracting travelers seeking a blend of relaxation and outdoor activities. Known for its stunning beach views and luxurious resorts, Wailea offers an array of activities, including golfing and shopping at high-end boutiques. Local landmarks, such as the beautiful bay and urban parks, invite visitors to unwind and enjoy the natural beauty of Hawaii. Whether you're lounging on the beach or exploring the scenic surroundings, Wailea is a perfect destination for those looking to soak in the sun.

Best time to go to Wailea Beach

If you're planning a trip to Wailea Beach, 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, March and July, while off-peak times, like August to October 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 SunnyAverageAverage
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 SunnySlightly HighAverage
August78.4°F (25.8°C)No Rain (Dry)Mostly SunnySlightly LowAverage
September78.4°F (25.8°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
October77.7°F (25.4°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
November75.7°F (24.3°C)No Rain (Dry)Mostly SunnyAverageAverage
December73.8°F (23.2°C)Light RainMostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Plus, extending your stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you become a part of our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin your savings journey.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board feature is designed to help you plan your travels effortlessly. It provides a convenient space for you to create new trips, pick up right where you left off, and organize all your travel plans in one place. You can easily access properties you've saved or booked, which are categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Wailea Beach?
The best vacation rentals near Wailea Beach are primarily located in the beautiful Wailea neighborhood of Kihei, Hawaii. You will find a great selection here, with condominiums being the most common style of home, alongside apartments. These properties offer convenient access to the beach and local attractions. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties and the best vacation rentals near Wailea Beach.

Many of these vacation rentals feature amenities like shared pools or private pools, as well as decks or patios for outdoor enjoyment. These homes are ideal for solo travelers, couples or small families looking for a relaxing escape.
Are there any cheap vacation rentals near Wailea Beach?
There are several affordable vacation rentals near Wailea Beach, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around $355 per night. You might find good deals in September and October. These rentals often include free amenities such as WiFi, toiletries, and self-parking, so you can have a comfortable stay.

To get the best value, consider staying slightly outside the immediate Wailea area. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. Many vacation rentals near Wailea Beach offer great value, providing a cozy and efficient base for your time in Hawaii.
What are the best pet-friendly vacation rentals near Wailea Beach?
There are dozens of pet-friendly vacation rentals near Wailea Beach, with 49 properties specifically welcoming pets. Many of these are condos and apartments located in the Wailea area, offering amenities that cater to both guests and their animal companions. You can expect features such as comfortable living spaces, fully equipped kitchens, and often private lanais for enjoying the Hawaiian breeze. These properties ensure a relaxing stay for everyone in your party.

When searching for the best pet-friendly vacation rentals near Wailea Beach, always review individual house rules for any specific pet policies, including potential size restrictions or additional fees. Wailea Beach itself is generally welcoming to pets, particularly in less crowded sections, providing ample space for walks along the shore.
What are the top vacation rentals with pools near Wailea Beach?
There are over 3,100 vacation rentals near Wailea Beach that offer access to swimming pools, with options ranging from private backyard pools to shared community facilities. These properties are predominantly found in the Wailea area, with many condominium and apartment homes providing various pool types. Many of these homes come equipped with standard amenities such as full kitchens, Wi-Fi, and comfortable living spaces, making them suitable for families or groups seeking both relaxation and adventure.

When selecting your ideal home, consider the benefits of different pool types. Private pools offer an exclusive experience, superb for families desiring seclusion, while shared pools often come with additional amenities like hot tubs or fitness centers. Given the pleasant climate, outdoor pools are a popular choice. For a truly enhanced stay, consider properties with heated pools during cooler evenings.
What are the best family vacation rentals near Wailea Beach?
There are over 2568 family-friendly vacation homes available near Wailea Beach, primarily in the Wailea area, offering ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, full kitchens for meal preparation, and outdoor play areas like patios, gardens, or secured yards. Many also include convenient amenities such as washer/dryers, and entertainment options like WiFi and video games.

When selecting the ideal family vacation rental, look for homes that provide separate areas for adults and children to ensure everyone has space to relax. Prioritize properties with practical amenities like a fully equipped kitchen to simplify meal times and laundry facilities to keep clothes fresh. Staying close to Wailea Beach means less travel time and more opportunities to enjoy the beautiful surroundings.
Are there any luxury vacation rentals near Wailea Beach?
Near Wailea Beach, guests can find several luxury vacation rentals that combine the natural scenery with modern comfort. These properties often feature amenities such as private pools, golf course access, infinity pools, deep soaking bathtubs, and stunning sea views. Many homes also boast gourmet kitchens, designer toiletries, and rainfall showerheads, ensuring a high-end stay.

These homes are ideal for families or larger groups, offering amenities like air conditioning and premium bedding. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Wailea Beach?
Vacation rentals near Wailea Beach offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties, such as simple apartments, typically start around $355 per night, providing an affordable option. Mid-range rentals, including private homes with standard amenities, are generally around $605 per night, offering more comfort and privacy. Upscale options can cost $885 or more per night, especially for properties with premium features or prime locations.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Wailea Beach?
When visiting Wailea Beach, several areas offer excellent vacation rental options. The immediate Wailea area provides properties within close proximity to Wailea Beach, making it ideal for those who prioritize beach access and stunning ocean views. You'll find a range of luxurious homes and apartments here.

As another option, properties in nearby Kihei offer a more laid-back vibe and are a short drive from Wailea Beach. Kihei provides a selection of vacation rentals that are often closer to local eateries and shops.

Further south, the Makena area offers secluded properties for a more private retreat, while still providing convenient access to Wailea Beach with a short drive.
What is the cheapest month to stay near Wailea Beach?
The cheapest time to find vacation rentals near Wailea Beach is typically during the late Summer to early Autumn (September to October). September is frequently the single cheapest month, often providing the best deals on homes and condos, with rates often 20% less compared to peak season. Guests can often find various savings during these months, along with greater availability.
Are there any top beachfront vacation rentals near Wailea Beach
Beachfront vacation rentals near Wailea Beach are concentrated along the immediate shoreline, offering guests properties with direct access to the sand and breathtaking ocean-view balconies. While some properties are within walking distance of lively dining and shopping areas, quieter spots nearby provide a more relaxed environment for those seeking tranquility.

Guests staying at these properties can often enjoy amenities such as beach chairs, umbrellas, and oceanfront pools. Accommodation types range from ocean-facing rooms and suites to multi-bedroom units, many featuring private terraces or ample living space, suitable for various group sizes.
Are there any monthly vacation rentals near Wailea Beach?
Vrbo offers excellent options for monthly vacation rentals near Wailea Beach, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Wailea Beach.
Are there any last-minute vacation rentals near Wailea Beach?
Vrbo makes it simple to find last-minute vacation rentals near Wailea Beach that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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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