A wooden sign for Keawa'i Church with a stone building and palm trees in the background.

Wailea-Makena vacation rentals

We found 4,985 vacation rentals — enter your dates for availability

Escape to the breathtaking shores of Wailea-Makena, where golden beaches meet azure waters and adventure awaits at every turn. Immerse yourself in the serene atmosphere of Wailea Beach and the family-friendly charm of Kamaole Beach Park, perfect for sun-soaked days. With a variety of luxurious vacation rentals—ranging from upscale condos to spacious homes—your group will find the ultimate comfort and convenience, ensuring a memorable Hawaiian getaway that feels just like home.

Holiday rentals with weekly discounts - Wailea-Makena

Showing deals for:Feb 12 - Feb 19

Hotel Zoned! Steps to the Beach, Dining and Shopping! Fall Specials! Inquire

Beach

Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!

Pool

Kihei Ocean View Haven | 1BR • AC • Pool • Kitchen

Enjoy stunning coastal views even while fixing a snack. The thoughtful, seamless layout flows effortlessly from the kitchen directly into the living space and out to your private oceanfront balcony.

10% off 7 days-Condo Ocean View 2BR, CENTRAL AC, Beach, Pool, Tennis, Pickleball

Ocean view condo

🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets

Property grounds

Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach

Living area

Maui Sunset B201: Beautiful 2 Bedroom, 2 Bath, Kihei Condo. Sleeps up to Six

Living Room

Fully Remodeled Modern Island Style!

Clubhouse pool and hot tub

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Find properties near top attractions in Wailea-Makena

A beach with palm trees, a row of beach umbrellas, and a green boat on the grass.

1

Wailea Beach

A beach with palm trees, a hotel, and the ocean.

2

Keawakapu Beach North

A beach with clear turquoise water, a person in the water, and a mountain in the background.

3

Maluaka Beach

A beach with clear blue water, a sandy shore, and a mountain in the background.

4

Kamaole Beach Park 3

A coastal landscape with a sandy beach, turquoise waters, and a hill with dense vegetation.

5

Makena State Park Beach

A dessert on a white plate with a strawberry and mint garnish.

6

Shops at Wailea

A beach with lush greenery, palm trees, and a clear blue ocean.

7

Polo Beach

A calm sea with a rainbow, palm trees, and a cloudy sky.

8

Ulua Beach

A beach with people sunbathing, umbrellas, and waves.

9

Little Beach

A coastal area with rocky shores, clear blue water, and lush greenery.

10

Makena Landing Park

Find the best place to stay - Wailea-Makena

Aston Maui Hill

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Sleeps 4

Wailea Ekahi - CoralTree Residence Collection

Image of Wailea Ekahi - CoralTree Residence Collection

Sleeps 2 · 1 bedroom

Upgraded unit with Panoramic Ocean and Mountain Views

Image of Upgraded unit with Panoramic Ocean and Mountain Views

Premier Host

Sleeps 5 · 2 bedrooms · 2 bathrooms

Makena Surf - CoralTree Residence Collection

Image of Makena Surf - CoralTree Residence Collection

Grand Champions by KBM

Image of Grand Champions by KBM

Sleeps 4 · 1 bedroom

Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Image of Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Premier Host

Sleeps 6 · 3 bedrooms · 2 bathrooms

Top rated rentals - Wailea-Makena

Spacious South Maui Vacation Rental with AC and Private Tropical Lanai

Image of Spacious South Maui Vacation Rental with AC and Private Tropical Lanai

Kihei Ali'i Kai Condos with Free Parking

Image of  Kihei Ali'i Kai Condos with Free Parking

Wonderful South Maui Beach Condos

Image of Wonderful South Maui Beach Condos

Awesome Maui Vista Beach Suite

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Find out more about Wailea-Makena

Why visit Wailea-Makena

Popular types of accommodation around Wailea-Makena

If you're planning a getaway to the stunning Wailea-Makena area, you're in for a treat. The most popular types of vacation rentals here include condos, houses, and apartments, all designed to enhance your Maui experience. From luxurious Wailea Resort options to charming Makena rentals and breathtaking oceanfront properties, including Wailea Beach Villas, you'll find the perfect accommodation for a memorable stay on the beautiful shores of Maui.

Top attractions near Wailea-Makena

Wailea-Makena, Hawaii, offers a perfect blend of beach, outdoor adventures, and stunning scenery, making it ideal for various travelers, including families. Explore its beautiful beaches, relaxing urban parks, and even nudist beaches for a unique experience. Whether you're looking to unwind by the ocean or enjoy family-friendly activities, Wailea-Makena has something for everyone to enjoy during your vacation.

Things to do recommended for couples

For a romantic getaway in Wailea-Makena, indulge in a soothing treatment at Makena Kai Day Spa, only 2 miles away. Savor delightful wines at MauiWine and Tedeschi Vineyards, both within 3 and 4 miles, offering enchanting settings perfect for couples to unwind and connect.

Things to do recommended for families

Families can have a blast at Science City, an exciting arcade and adventure zone located 12 miles from Wailea-Makena. With its fun and adventurous atmosphere, it's the perfect spot for kids to enjoy games and activities while creating lasting memories together.

Things to do recommended for groups

Your group can enjoy shopping and entertainment at the Shops at Wailea, just 1 mile away. For outdoor fun, play a round at the Wailea Gold Golf Course, only 0.3 miles away. Don't miss the Maui Brewing Co. for a taste of local craft beers, located 6 miles from your stay.

*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-Makena

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful booking tips for Vrbo to assist you.

Where to stay near Wailea-Makena

Wailea-Makena is a tropical paradise perfect for those seeking a beach vacation or outdoor adventures. With stunning Wailea Beach as a highlight, visitors can enjoy romantic sunsets and family-friendly activities. Explore the secluded beauty of Makena, indulge in a Maui getaway, and experience the charm of vacation homes in the Hawaiian Islands. Whether you're looking for relaxation or excursions, this region offers an unforgettable escape filled with breathtaking scenery.

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can help, as prices often vary. Additionally, booking a longer stay typically offers significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for planning your travels. You can easily start new trips, resume planning from where you last stopped, or review and arrange your travel details. Your saved or booked properties will be neatly organized into categories like Potential, Upcoming, and Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently Asked Questions

What is the most popular type of vacation rental accommodation in Wailea-Makena?

Condos are the most popular kind of vacation rental in Wailea-Makena, according to our data. Even if you've got something else in mind, Vrbo has properties in many sizes and shapes. Browse our many options to find your perfect pad.

How much does it cost to rent a vacation rental in Wailea-Makena?

Different things can determine what you'll pay for a vacation rental in Wailea-Makena, like the season, type of property and length of stay. Still, all of our vacation homes have something in common — amazing value. Simply enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Wailea-Makena?

Prices for beach houses in Wailea-Makena differ depending on the style and size of the property and when you plan to travel. All you have to do is enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use the filters to narrow your search results by nearby activities, ratings, amenities and more.

Are there pet-friendly vacation rentals in Wailea-Makena?

With three vacation rentals that welcome four-legged guests, your furry companion can join in the fun on your Wailea-Makena vacation. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.

Are there large group vacation rentals in Wailea-Makena?

With 46 properties that can host 10 or more people in Wailea-Makena, there's no need to keep your invite list short. From extended family vacations to special events like birthday and Christmas parties, Vrbo will help you find a large group rental that fits the occasion.

What are the top attractions for families in Wailea-Makena?

Keeping the kiddos entertained during your vacation in Wailea-Makena is child's play with these exciting family-friendly attractions:

Are there one-bedroom vacation rentals in Wailea-Makena?

Yes, you'll find 1,039 one-bedroom properties in Wailea-Makena to choose from. A one-bedroom vacation rental is a superb choice if it's just you and your other half or if you're flying solo. Add in more privacy, convenience and space than a standard hotel, and you have yourself an unforgettable getaway.

Can I find two-bedroom vacation rentals in Wailea-Makena?

Wailea-Makena has 975 two-bedroom properties to choose from. Go for a vacation home with all the comfort and privacy you want at an attractive price on Vrbo.

Are there vacation rentals with WiFi in Wailea-Makena?

Choose from 1,164 vacation rentals with WiFi in Wailea-Makena. If you want to disconnect from daily life during your trip, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Wailea-Makena?

Select your dates and then make use of our filters to search for vacation rentals with air conditioning in Wailea-Makena on Vrbo. With 2,043 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.

How old do you have to be to rent a vacation rental in Wailea-Makena?

The minimum age is normally 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your preferred Wailea-Makena stay before making a booking.

How long can I rent a vacation rental in Wailea-Makena for?

It all depends on the Wailea-Makena property. To view a list of options offering extended stays, simply type your travel dates and number of people into Vrbo's search page. You can enjoy having the entire place to yourself, as well as amenities such as air conditioning, a kitchen and a yard where your little ones can play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

Does Vrbo offer discounts for vacation homes in Wailea-Makena?

In Wailea-Makena, you'll find amazing deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a weekend getaway or a few weeks away, we've got a variety of options to suit your style.

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