Wailea-Makena vacation rentals

We found 4,751 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:Nov 6 - Nov 13

Lobby
View on the pool
Salt water pool
Lobby
Exceptional
(253 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

9% off
$560
$3,917 for 7 nights
All fees included
Mana Kai Maui Condo - Right on the Beach!
Living Room from Master Bedroom Railing
Lower Swimming Pool
Living Room
Entry Sign by Kihei Rd
Exceptional
(95 reviews)

D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.

Kihei

6% off
$441
$3,090 for 7 nights
All fees included
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Property grounds
Room
Pool
Exterior
Wonderful
(17 reviews)

Charming Studio at Maui Banyan Resort - Walk to Beach, Pools, AC, Beach Gear

Kihei

8% off
$161
$1,128 for 7 nights
All fees included
Charming Studio at Maui Banyan Resort - Walk to Beach, Pools, AC, Beach Gear
View from lanai towards ocean
View from lanai before sunrise coming up over Haleakala
Kamaole Sands panorama
Pool area looking towards ocean
Exceptional
(92 reviews)

Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1

Kihei

8% off
$504
$3,526 for 7 nights
All fees included
Unbeatable Location at Kamaole III Beach - Kam Sands Bldg. 1
Property grounds
Outdoor dining
Living area
Pool
Exceptional
(51 reviews)

Ekahi 27A: Priceless Ocean View from a Private Lanai

Kihei

13% off
$518
$3,625 for 7 nights
All fees included
Ekahi 27A: Priceless Ocean View from a Private Lanai
Lanai view
Exterior
Great bedroom with king bed
Living area
Exceptional
(110 reviews)

Oceanview Top Floor Condo, with Internet Access.

Kihei

8% off
$211
$1,475 for 7 nights
All fees included
Oceanview Top Floor Condo, with Internet Access.
Parking at the Maui Banyan is convenient and covered
Maui Tropical Plantation.
Freds Mexican Cafe & Moose's is located just across the street from Kamaole II.
Just one of Maui's great golf courses to test you skills.
Exceptional
(29 reviews)

TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b

Kihei

10% off
$210
$1,472 for 7 nights
All fees included
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Kamaole Sands resort amenities include pools, hot tubs, gym and tennis.
Relax in your private lanai and enjoy the ocean view. This is paradise!
Feel right at home in this fully-equipped kitchen with granite countertops.
Pool
Exceptional
(89 reviews)

Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!

Kihei

8% off
$289
$2,025 for 7 nights
All fees included
Maui Escape - Oceanview 70 Yds to Beach, GND Flr, Bldg10 - Everything You Need!
Grounds outside our Lanai
View from Lanai
Lower Swimming {Pool from our Lanai
Lower Swimming Pool
Exceptional
(59 reviews)

# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach

Kihei

7% off
$247
$1,732 for 7 nights
All fees included
# 107 Lovely Grnd Flr King bed Unit, accross the street is a white sand beach
view from lanai over the complex grounds
Property grounds
Living area
Private kitchen
Exceptional
(164 reviews)

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kihei

8% off
$335
$2,346 for 7 nights
All fees included
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Kamaole Sands grounds
Our beloved 5 Palms is gone but new restaurant slated to open here December 2023
Outdoor dining
Living area
Exceptional
(89 reviews)

Beautifully renovated luxury condo steps from the sand on premier Kihei beach!

Kihei

8% off
$232
$1,622 for 7 nights
All fees included
Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
Living area
Property grounds
Beach
Pool
Exceptional
(64 reviews)

Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout

Kihei

8% off
$220
$1,540 for 7 nights
All fees included
Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout
Miscellaneous
Close to the swimming pool with Jacuzzi and BBQs
Living room
Master Bedroom on golf course with ocean view
Wonderful
(101 reviews)

Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.

Kihei

9% off
$266
$1,865 for 7 nights
All fees included
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Exterior
Appreciate the easy beach access from the pavilion pool.  (1 of 4 pools)
Golf
Ocean View from the front door!
Exceptional
(93 reviews)

Wailea Ekahi 54A: Remodeled & Panoramic Ocean View.

Kihei

8% off
$688
$4,814 for 7 nights
All fees included
Wailea Ekahi 54A: Remodeled & Panoramic Ocean View.
Property grounds
Property grounds
Living area
Interior
Exceptional
(55 reviews)

Updated Designer Condo w/ Ocean Views within five minutes to the beach

Kihei

8% off
$330
$2,308 for 7 nights
All fees included
Updated Designer Condo w/ Ocean Views within five minutes to the beach
Kitchen
Property grounds
Bar area and front door
Dining area
Exceptional
(14 reviews)

NEWLY REMODELED! Partial Ocean View condo along the golf course

Kihei

8% off
$686
$4,805 for 7 nights
All fees included
NEWLY REMODELED! Partial Ocean View condo along the golf course
Pool
Outdoor dining
Living area
Interior
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

8% off
$386
$2,703 for 7 nights
All fees included
Kihei Getaway in Paradise
Pool
Living Room
Kitchen
Living Room
Exceptional
(168 reviews)

Wailea 1 BR Condo, close to everything, good pricing

Kihei

8% off
$278
$1,948 for 7 nights
All fees included
Wailea 1 BR Condo, close to everything, good pricing
Kitchen bar view
Clubhouse pool and hot tub
Common Garden area
Kitchen
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

8% off
$648
$4,538 for 7 nights
All fees included
Fully Remodeled Modern Island Style!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Wailea-Makena

Why visit Wailea-Makena

  • Stunning Beaches: Enjoy the breathtaking Wailea Beach, perfect for sunbathing, swimming, and picturesque sunsets.
  • Outdoor Adventures: Explore the diverse outdoor activities, from hiking trails to water sports, ideal for adventure seekers.
  • Family-Friendly Activities: Engage in various attractions and parks suitable for visitors of all ages.
  • Unique Experiences: Discover secluded spots in Makena, including nudist beaches for a one-of-a-kind experience.
  • Luxurious Accommodations: Choose from elegant condos and oceanfront properties that enhance your Maui getaway.

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.

  • Condos: The top choice for travelers in Wailea-Makena, offering convenient amenities and stunning views.
  • Houses: A great option for families or groups, providing spacious living and a home-like atmosphere.
  • Apartments: Ideal for those seeking a comfortable and affordable stay with easy access to local attractions.
  • Villas: Luxurious accommodations with upscale features, perfect for those wanting an indulgent getaway.
  • Cottages: Quaint and charming, these provide a cozy escape for a romantic or peaceful retreat.**

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.

  • Wailea Beach: A picturesque stretch of golden sand, Wailea Beach offers a serene atmosphere perfect for sunbathing and swimming. Its calm waters and stunning sunsets create an idyllic setting for relaxation and beach vibes.
  • Makena State Park Beach: Known for its romantic vibes, this clothing-optional beach invites you to enjoy the sun and surf in a liberating environment. The breathtaking scenery and secluded feel make it a unique getaway.
  • Kamaole Beach Park 3: A family-friendly urban park featuring soft sand and gentle waves, Kamaole Beach Park 3 is perfect for picnics and outdoor activities. Its vibrant atmosphere caters to both relaxation and fun.

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.

  • Traveling to Wailea-Makena with a group: Think about how many bedrooms you require, along with additional features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search on Vrbo to include all of these options and more.
  • Traveling to Wailea-Makena with young kids: Traveling with young kids can be quite a task. It's essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wailea-Makena: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Wailea-Makena: 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 options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

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.

  • Maui: Maui is a stunning island known for its breathtaking natural beauty and diverse outdoor activities. Located 11 miles from Wailea-Makena, this tropical paradise attracts visitors with its pristine beaches, scenic landscapes, and vibrant culture. Explore world-class golf courses, indulge in shopping at local centers, or relax at serene beaches and picturesque bays. Maui’s urban parks offer a great place for families and friends to enjoy picnics and outdoor fun, making it an ideal destination for nature lovers and adventure seekers alike.
  • Kihei: Kihei is a charming city situated just 7 miles from Wailea-Makena, offering a warm, family-friendly atmosphere. Known for its beautiful beaches and outdoor spaces, Kihei is perfect for sunbathing, swimming, and beachside activities. The city features several golf courses and shopping centers, making it easy for visitors to enjoy leisure time. With its inviting family beaches and urban parks, Kihei is a great spot for those looking to create lasting memories with loved ones while soaking up the sun in this tropical setting.
  • Wailea: Wailea is an upscale neighborhood located merely 1 mile from Wailea-Makena, renowned for its luxurious resorts and stunning ocean views. This picturesque area is famous for its beautiful beaches and lush landscapes, attracting travelers seeking relaxation and outdoor adventures. Visitors can enjoy top-notch golf courses, shopping, and fine dining options. With easy access to urban parks and scenic bays, Wailea offers a perfect blend of tranquility and excitement for those looking to enjoy Hawaii’s natural beauty.

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.

Find the perfect vacation rental for your Wailea-Makena getaway

Learn about the unique charm of Wailea-Makena with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Haleakala National Park and Wailea Beach are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Wailea-Makena

Are you looking for things to do during your stay? Venture out of your cozy vacation rental and experience everything that Wailea-Makena has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Maui Nui Golf Club (5.6 mi / 9 km)
  • Maui Spa Retreat (14.3 mi / 23 km)
  • Wailea Emerald Golf Course (0.3 mi / 0.4 km)
  • Wailea Gold Golf Course (0.3 mi / 0.5 km)
  • Wailea Blue Golf Course (0.4 mi / 0.7 km)
  • Makena South Course (1.6 mi / 2.6 km)

Exploring the natural features in Wailea-Makena

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Wailea-Makena is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Haleakala National Park (18.3 mi / 29.4 km)
  • Wailea Beach (0.9 mi / 1.5 km)
  • Polo Beach (0.6 mi / 1 km)
  • Maluaka Beach (1.6 mi / 2.6 km)
  • Ulua Beach (1.6 mi / 2.6 km)
  • Keawakapu Beach North (2.5 mi / 4 km)

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:
  • Keawakapu Beach North
  • Makena State Park Beach
  • Wailea Beach
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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