Wailea-Makena vacation rentals

We found 4,761 vacation rentals — enter your dates for availability

Holiday rentals with weekly discounts - Wailea-Makena

Showing deals for:Dec 11 - Dec 18

Living area
Private kitchen
Fitness facility
Pool
Exceptional
(76 reviews)

Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!

Kihei

5% off
CA $1,500
CA $14,556 total
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Dining
Outdoor dining
Living area
Pool
Exceptional
(40 reviews)

Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling

Kihei

8% off
CA $1,459
CA $14,021 total
Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling
Guest room with XL twins or king—great for couples, kids, or friends.
Relax in oceanfront luxury with beach views, sunsets, and breezy lanai mornings.
Your expansive indoor outdoor lanai has a beautiful Maui view
Wake up to island beauty with local art and tropical Maui-inspired style.
Exceptional
(93 reviews)

Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles

Kihei

7% off
CA $1,149
CA $11,124 total
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
Living area
Beach
Exterior
Private kitchen
Exceptional
(44 reviews)

Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

Kihei

5% off
CA $245
CA $2,769 total
Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
Lobby
View on the pool
Spacious lanai with enough seating for the whole family.
Lobby
Exceptional
(256 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

10% off
CA $646
CA $6,220 total
Mana Kai Maui Condo - Right on the Beach!
Dining
Beach
Pool
Room
Exceptional
(15 reviews)

Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC

Kihei

5% off
CA $557
CA $5,727 total
Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC
Interior
Property grounds
Outdoor dining
Interior
Exceptional
(31 reviews)

Hale Hui Kai 106 - Beautiful Ground Floor Unit, on Keawakapu Beach, Split AC!

Kihei

5% off
CA $608
CA $6,239 total
Hale Hui Kai 106 - Beautiful Ground Floor Unit, on Keawakapu Beach, Split AC!
Beach
Property grounds
Interior
Pool
Exceptional
(97 reviews)

Mana Kai 410 - The Ultimate Maui Beach Condo Experience - Renovated - Split AC

Kihei

5% off
CA $686
CA $6,874 total
Mana Kai 410 - The Ultimate Maui Beach Condo Experience - Renovated - Split AC
Miscellaneous
Close to the swimming pool with Jacuzzi and BBQs
Master Bedroom on golf course with ocean view
View of the 2nd hole
Wonderful
(101 reviews)

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

Kihei

10% off
CA $311
CA $2,968 total
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Pool
Living area
Exterior
Property grounds
Exceptional
(91 reviews)

Maui Kamaole G-202 - Spectacular Views, Updated and Elegant, Wi-Fi & Split-AC!

Kihei

5% off
CA $502
CA $5,317 total
Maui Kamaole G-202 - Spectacular Views, Updated and Elegant, Wi-Fi & Split-AC!
Interior
Room
Pool
Property grounds
Exceptional
(53 reviews)

Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!

Kihei

5% off
CA $605
CA $6,208 total
Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!
Barbeque Area in Gazebo and near pool area
Oasis Pool with waterfall, Cabana, Kitchen, additional BBQs and Restrooms
Dining
Entrance to Pool Area
Exceptional
(177 reviews)

Maui Kamaole CONDO M102 TOTALLY RENOVATED

Kihei

10% off
CA $279
CA $2,917 total
Maui Kamaole CONDO M102 TOTALLY RENOVATED
Living area, dining, and kitchen
Granite countertop, living area
Living area looks out to lanai and lush landscaping
Dining area, kitchen
Exceptional
(140 reviews)

Kihei, Maui Ground Floor Tropical Getaway - Across street from beach

Kihei

10% off
CA $242
CA $2,441 total
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Pool
Outdoor dining
Property grounds
Beach
Exceptional
(32 reviews)

Hale Hui Kai 202 - Keawakapu Beach, Garden Views, Steps to the Beach, Split AC!

Kihei

5% off
CA $611
CA $6,260 total
Hale Hui Kai 202 - Keawakapu Beach, Garden Views, Steps to the Beach, Split AC!
Pool
Property grounds
Living area
Property grounds
Exceptional
(46 reviews)

Experience Kamaole Sands 6-202, Stunning Renovation, Ocean View, Wi-Fi, Split AC

Kihei

5% off
CA $283
CA $3,286 total
Experience Kamaole Sands 6-202, Stunning Renovation, Ocean View, Wi-Fi, Split AC
Private kitchen
Living area
Living area
Living area
Exceptional
(169 reviews)

Beautiful Kamaole Beach Park two bed two bath Condo

Kihei

5% off
CA $361
CA $3,585 total
Beautiful Kamaole Beach Park two bed two bath Condo
Custom Made Built-in TV Closet System
Dine and Enjoy the Ocean View
Sofa and Comfy Chair
Living area
Exceptional
(167 reviews)

Freshly Renovated Corner Studio With View of the Ocean

Kihei

5% off
CA $262
CA $2,644 total
Freshly Renovated Corner Studio With View of the Ocean
Living area
Outdoor dining
Exterior
Private kitchen
Exceptional
(109 reviews)

Maui Parkshore 307 - Stunning Ocean View 2bd / 2ba Overlooking Kamaole III Beach

Kihei

5% off
CA $371
CA $4,007 total
Maui Parkshore 307 - Stunning Ocean View 2bd / 2ba Overlooking Kamaole III Beach
Sport court
Pool
Living area
Beach
Exceptional
(58 reviews)

Maui Kamaole J-104 - Renovated, Private Ground Floor Unit, Two Lanais, Split AC!

Kihei

5% off
CA $289
CA $3,281 total
Maui Kamaole J-104 - Renovated, Private Ground Floor Unit, Two Lanais, Split AC!
Dining
Outdoor dining
Exterior
Pool
Exceptional
(5 reviews)

Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC

Kihei

5% off
CA $535
CA $5,429 total
Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC
Pool
Interior
Exterior
Living area
Exceptional
(58 reviews)

Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!

Kihei

5% off
CA $542
CA $5,741 total
Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!
View from Keawakapu Beach
Outdoor dining
Private kitchen
View from the heated pool.
Exceptional
(79 reviews)

Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned

Kihei

10% off
CA $807
CA $7,309 total
Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned
Fitness facility
Property grounds
Outdoor dining
Exterior
Exceptional
(128 reviews)

Kamaole Sands 10-307, Ocean View, Large Lanai, Twin Murphy Beds, Split-AC, Wi-Fi

Kihei

5% off
CA $389
CA $4,253 total
Kamaole Sands 10-307, Ocean View, Large Lanai, Twin Murphy Beds, Split-AC, Wi-Fi
Living area
Pool
Dining
Interior
Exceptional
(28 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

10% off
CA $1,863
CA $16,497 total
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Find out more about Wailea-Makena

Why visit Wailea-Makena

  • Stunning beaches: Enjoy the pristine sands of Wailea Beach and Makena Beach, perfect for relaxation and sunbathing.
  • Scenic pathways: Stroll along the picturesque Wailea Beach Path, offering breathtaking ocean views.
  • Outdoor activities: Explore urban parks and secluded coves, ideal for families and outdoor enthusiasts.
  • Local culture: Indulge in authentic Hawaiian cuisine and experience Maui's vibrant culture just minutes away.
  • Variety of accommodations: Choose from luxurious resorts or cozy vacation rentals to suit your holiday needs.

Popular types of accommodation around Wailea-Makena

Planning a getaway to Wailea-Makena? You're in for a treat. This stunning destination offers a variety of top-notch accommodations, including condos, houses, and apartments. Whether you're looking for a luxurious Wailea resort or a cozy Makena rental, you'll find the perfect vacation rental that fits your needs. Enjoy the breathtaking scenery and make unforgettable memories in this beautiful corner of Hawaii.

  • Condos: The most sought-after option in Wailea-Makena, offering modern amenities and stunning views, ideal for vacationers.
  • Houses: A top choice for those seeking spacious accommodations, perfect for families or groups wanting privacy.
  • Apartments: A popular alternative, providing convenient living spaces for couples or solo travellers looking for comfort.
  • Villas: Luxurious and often equipped with private pools, these are perfect for a lavish getaway.
  • Cottages: Quaint and charming, these offer a cozy escape for those seeking a more intimate atmosphere.**

Top attractions near Wailea-Makena

Wailea-Makena is perfect for a beach and outdoor vacation, offering stunning scenery and various attractions. Popular points of interest include beautiful beaches such as Wailea Beach and Makena Beach, along with the scenic Wailea Beach Path. Families and outdoor enthusiasts will appreciate the urban parks and even nudist beaches nearby. Don't forget to explore the shops at Wailea for a complete experience during your visit.

  • Wailea Beach: A stunning stretch of golden sand, Wailea Beach offers a relaxing atmosphere perfect for sunbathing and swimming. The beach vibes create an inviting environment, making it an ideal spot for leisurely strolls along the shore and enjoying breathtaking sunsets.
  • Makena State Park Beach: Known for its romantic vibes, this nudist beach is a serene paradise that allows for a unique and liberating experience. The picturesque scenery and tranquil waters make it perfect for couples looking to connect with nature.
  • Kamaole Beach Park 3: This family-friendly urban park features lush green spaces, picnic areas, and easy beach access. With its vibrant outdoor atmosphere, it’s a fantastic spot for families to enjoy a day of fun in the sun.

Things to do recommended for couples

Wailea-Makena offers a perfect romantic getaway for couples. Indulge in rejuvenating treatments at Makena Kai Day Spa, savor delightful wines at MauiWine and Tedeschi Vineyards, both just a short drive away. Enjoy the scenic beauty and intimate atmosphere that make for unforgettable memories together.

Things to do recommended for families

Families visiting Wailea-Makena can enjoy a thrilling day at Science City, an exciting arcadeAdventureZone located 19.3km away. With its vibrant atmosphere and engaging activities, it's perfect for creating lasting memories together.

Things to do recommended for groups

In Wailea-Makena, your group can shop at the Shops at Wailea for a lively experience, tee off at the Wailea Gold Golf Course for some outdoor fun, and unwind with craft brews at Maui Brewing Co., just a short drive away.

*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

If you're planning a trip with friends, family, pets, or need accommodations for an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wailea-Makena 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-Makena with young kids: Travelling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Wailea-Makena: For many families, a trip wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea-Makena: If you’re searching for vacation rentals with discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including amenities like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Wailea-Makena

Wailea-Makena offers an idyllic Hawaiian getaway with stunning beaches and lush outdoor scenery. Just minutes from Maui's vibrant culture, you'll find romantic and family-friendly experiences perfect for relaxation and adventure. Explore secluded coves, indulge in local cuisine, and bask in the sun on beautiful shores. This captivating region promises unforgettable excursions, making it a prime destination for your Maui vacation.

  • Maui: Maui is a stunning island located 17.7km away from Wailea-Makena. Renowned for its exceptional outdoor experiences, breathtaking beaches, and captivating scenery, Maui offers a diverse range of activities. Visitors can enjoy world-class golf courses, explore local shopping centres, and relax on beautiful beaches. Key attractions include picturesque bays and urban parks, making it a perfect destination for those seeking both adventure and relaxation amidst nature's beauty.
  • Kihei: Situated 11.3km from Wailea-Makena, Kihei is a vibrant city known for its family-friendly atmosphere and stunning beaches. Kihei is ideal for outdoor enthusiasts, offering various activities such as golfing and water sports. The city boasts lively shopping centres and beautiful urban parks, along with family-oriented beaches that are perfect for a day in the sun. With its welcoming community vibe and scenic coastline, Kihei is an excellent choice for travelers seeking both fun and relaxation.
  • Wailea: Wailea is a luxurious neighborhood located a mere mile from Wailea-Makena, famous for its pristine beaches and stunning ocean views. This upscale area is perfect for those looking to indulge in outdoor activities and enjoy picturesque scenery. Wailea features several acclaimed golf courses, upscale shopping options, and beautiful parks. Visitors can unwind on its stunning beaches or explore the scenic bays, making Wailea a tranquil yet luxurious getaway.

Booking with Vrbo is simple

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial 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 spot for your next adventure.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.vrbo.com/en-ca/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. Wailea Beach and Haleakala National Park 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:

  • Wailea Emerald Golf Course (0.3 mi / 0.4 km)
  • Wailea Gold Golf Course (0.3 mi / 0.5 km)
  • Maui Nui Golf Club (5.6 mi / 9 km)
  • Maui Spa Retreat (14.3 mi / 23 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:

  • Wailea Beach (0.9 mi / 1.5 km)
  • Haleakala National Park (18.3 mi / 29.4 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 best area to stay in Wailea-Makena when booking a vacation rental?
Makena is one of the more popular locations to find a vacation home in Wailea-Makena. Searching for some awesome things to see and do in this destination? Be sure to check out Makena State Park Beach and Maluaka Beach.
What is the most popular type of vacation rental accommodation in Wailea-Makena?
The most popular types of vacation rentals in Wailea-Makena are condos. Ready for more choices? Vrbo offers a variety of options to match the diverse needs of our guests, so you'll see properties in lots of sizes and shapes. The ideal home away from home is waiting for you — snap up yours today.
How much does it cost to rent a vacation rental in Wailea-Makena?
The average price for a vacation rental in Wailea-Makena is determined by a number of factors, including length of stay, season and property type. Whether you'd like a sprawling villa with space for the whole family or a cozy cottage for just you and your sweetheart, just add your dates of travel to see stays with unbeatable value.
How much does it cost to rent a beach house in Wailea-Makena?
The average price for a vacation rental close to the beach in Wailea-Makena depends on when you're visiting the area and the style and size of property you're searching for. You can easily and quickly find prices on Vrbo by entering your destination and preferred travel dates. Then use our filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.
What are popular rental amenities in Wailea-Makena?
The most popular rental amenities people are searching for in Wailea-Makena include a stovetop, a fridge and a microwave oven. Whether you're on a trip with pals, family or even pets, Vrbo vacation homes have the best amenities for fun and relaxation with the people that matter most.
Are there large group vacation rentals in Wailea-Makena?
Choose from 12 properties in Wailea-Makena that can sleep 10 or more people. Whether you're organizing a family vacation or some kind of special event, there's plenty of space to get your favorite people together under the same roof.
What are the top attractions for families in Wailea-Makena?
You'll find loads of fun things to do and see with the family in Wailea-Makena, such as:
  • Keawakapu Beach North
  • Wailea Beach
  • Makena State Park Beach
Can I find two-bedroom vacation rentals in Wailea-Makena?
You can select from 966 two-bedroom vacation rentals in Wailea-Makena. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's plenty of space for whoever's fortunate enough to be coming along.
Are there vacation rentals with WiFi in Wailea-Makena?
Whether you want to keep up with the news, reply to emails or surf social networks, there are 1,102 vacation homes with WiFi in Wailea-Makena. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How old do you have to be to rent a vacation rental in Wailea-Makena?
The minimum age permitted can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Wailea-Makena you want to book. But normally, it's 16, 18 or 21.
How long can I rent a vacation rental in Wailea-Makena for?
The amount of time you can rent a Wailea-Makena vacation rental for depends on the property. Just enter your travel dates to browse options offering longer term stays. They come with the things you need to make your extended getaway more enjoyable and convenient, such as laundries and air conditioning. Some Vrbo vacation homes may also offer discounted weekly or monthly prices, so you can hang around longer for less.

More Vacation Ideas