Wailea-Makena Vacation Rentals from CA $211: Short-Term Rentals for 2026

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Our top choices for Wailea-Makena vacation rentals

A resort with a swimming pool, palm trees, and ocean views.

1. Aston Maui Hill

South Kihei

Megan

CA $487 total

includes taxes & fees

Dec 10 - Dec 11

A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

2. Grand Champions by KBM

Wailea

Sean

CA $1,511 total

includes taxes & fees

Dec 1 - Dec 2

A golf course with a clear view of the ocean and a row of houses in the background.

3. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

Wailea

Rojelio G.

CA $979 total

includes taxes & fees

Nov 25 - Nov 26

A swimming pool with a turtle, surrounded by palm trees and a building with balconies.

4. Romantic 1 BR Condo with King Tempurpedic

Wailea

Kathryn R.

CA $534 total

includes taxes & fees

Nov 18 - Nov 19

A wooden table with a bottle of wine and two glasses on a balcony overlooking a lush garden and the ocean.

5. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

Wailea

Scott M.

CA $867 total

includes taxes & fees

Nov 18 - Nov 19

A resort with a swimming pool, palm trees, and hanging decorative spheres.

6. Wailea Ekahi 29C, Ocean View, Steps away from the pool

Wailea

Corey R.

CA $1,476 total

includes taxes & fees

Dec 6 - Dec 7

A spacious living area with a glass table, wooden chairs, a sofa, and a view of the ocean through large windows.

7. Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

Wailea

Nick D.

CA $1,268 total

includes taxes & fees

Dec 4 - Dec 5

An outdoor patio with a grill, seating, and a view of the ocean.

8. Ekahi 27A: Priceless Ocean View from a Private Lanai

Wailea

Petr K.

CA $1,357 total

includes taxes & fees

Nov 24 - Nov 25

An aerial view of a hotel with a central swimming pool, multiple lounge areas, and lush greenery.

9. Luxury Condo on Wailea Blue Golf Course

Wailea

Bryce

CA $986 total

includes taxes & fees

Nov 30 - Dec 1

A resort with a central pool, palm trees, and a well-maintained lawn.

10. Romantic, Luxury Maui Getaway with Ocean View - Couples Only

Wailea

Roger B.

CA $905 total

includes taxes & fees

Nov 17 - Nov 18

A balcony with wicker furniture, a table, and a view of a golf course and buildings.

11. Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

Wailea

Matthew M.

CA $662 total

includes taxes & fees

Nov 16 - Nov 17

A pool with palm trees and lounge chairs.

12. Wailea Ekahi Village WKV-45C by KBM

Wailea

Chelsea

CA $1,788 total

includes taxes & fees

Dec 5 - Dec 6

A resort with a swimming pool, palm trees, and a view of the ocean.

13. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

Wailea

Marcie M.

CA $730 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and white chairs.

14. StunningRenoPalms in Wailea Condo-BeachGolf*Pool

Wailea

Nick F.

CA $730 total

includes taxes & fees

Nov 30 - Dec 1

A breakfast table set on a balcony with a view of a tropical landscape.

15. Signature Residences at Maui Banyan

South Kihei

Mai

CA $796 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a curved design, surrounded by palm trees and a golf course.

16. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

Wailea

Darren P.

CA $1,425 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with clear blue water, surrounded by palm trees and a building with balconies.

17. Romantic, Luxury, Sensual Retreat - Couples Only

Wailea

Jessica N.

CA $972 total

includes taxes & fees

Nov 22 - Nov 23

18. Cozy, Well-Furnished Studio

Wailea

"Wonderful bed, slept very well. Large bathroom with plenty of counter space. A tiny tiny kitchenette. Had not realized that we’d have to stand on someone else’s balcony in front of their sliding glass doors, in order to do laundry, or that laundry could only be done in daylight hours. (It’s much preferable for us, while on vacation, to do laundry at night.) Well-stocked room. Would stay again."

Lisa Q.

CA $490 total

includes taxes & fees

Nov 28 - Nov 29

A pool area with palm trees, lounge chairs, and a view of the ocean.

19. Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

Wailea

Sandi G.

CA $1,694 total

includes taxes & fees

Nov 13 - Nov 14

A hotel room with a balcony, a desk, a chair, a bed, and a ceiling fan.

20. Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

South Kihei

Paul B.

CA $838 total

includes taxes & fees

Nov 20 - Nov 21

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Find vacation rentals that suit your style

Top Wailea-Makena Hotel Reviews

A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

Four Seasons Resort Maui at Wailea

Wailea

10/10 Excellent

This was our second stay at Four Seasons in Wailea-rooms have been renovated since our last stay. Attentive staff and fun kids camp for kids starting at age 5. Pool with cabanas are never too crowded but you need to go early to reserve a cabana-they will hold it for you for an hour. We went into Kihei for meals but also enjoyed eating in the lobby/bar area to watch hula dancing performance in the evenings. Overall a wonderful spring break with the kids. Breakfast can be pricey at the resort but...

aoli

A staircase with a view of a garden, palm trees, and a bridge.

Fairmont Kea Lani Maui

Wailea

10/10 Excellent

Jessica

A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

Ho‘olei Villas at Grand Wailea

Wailea

10/10 Excellent

Overall, our stay at Ho’olei was wonderful, as always! We were a party of eight, and the three-bedroom villa was the perfect setup for our family. There was something for everyone to enjoy, especially the kids. We loved the fitness classes, the pools on both sides of the property, the dining options, and the Fourth of July festivities. The villa was spotless, spacious, and very comfortable. One of our favorite parts of the trip was enjoying dinner on the lanai while watching the beautiful...

Stephanie

A balcony with a view of the ocean and palm trees.

Maui Coast Hotel

South Kihei

10/10 Excellent

Paulino Cabalona

A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

Kihei Ali'i Kai Condos with Free Parking

South Kihei

10/10 Excellent

Nadia

A spacious balcony with wicker furniture, a view of the ocean, and a mountain in the distance.

Hilton Grand Vacations Club Maui Bay Villas

North Kihei

10/10 Excellent

Kristina

Nona Lani Cottages

North Kihei

10/10 Excellent

We decided to stay at the Nona Lani cottages to get away from a big hotel experience and it did not dissapoint. It's an authentic beachfront Hawaiian experience. We loved the ability to cook our own meals, particularly with the time change. I'm not sure you can get a coffee at 3am at one of the larger hotel chains. The cottages are super cute and the hosts are fantastic and are a wealth of information. They provided us with beach chairs and gave us information that only locals can provide....

Stephanie

A resort with multiple swimming pools, palm trees, and a view of the ocean.

Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

10/10 Excellent

Anonymous traveller

A poolside lounge area with outdoor seating, a fire feature, and umbrellas providing shade.

AC Hotel by Marriott Maui Wailea

Wailea

10/10 Excellent

Roger

A modern bar area with a long counter, multiple stools, and a large TV screen displaying a scenic view.

Residence Inn by Marriott Maui Wailea

Wailea

10/10 Excellent

Jessica

A swimming pool with lounge chairs and palm trees.

Courtyard Maui Kahului Airport

Kahului

10/10 Excellent

This was our first stay at the Courtyard Maui Kahului Airport. We flew into Kahului late in the evening, and were greeted by friendly staff who checked us in quickly. We only stayed one night, as we were flying out of the Kahului airport the next day to another island. For this, the location was perfect. Our room was very clean, and had everything we needed (WiFi, coffee, hair dryer, closet, plenty of pillows). The shower was very spacious, had a glass enclosure with a door that did not leak...

eternalsummer

Find out more about Wailea-Makena

Everything you need to know about Wailea-Makena vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wailea-Makena vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wailea-Makena vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wailea-Makena vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wailea-Makena. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wailea-Makena vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wailea-Makena vacation rentals we have selected for you start as low as CA $211 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wailea-Makena rentals

At Expedia, we put the best Wailea-Makena vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wailea-Makena rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wailea-Makena vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wailea-Makena. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Wailea-Makena Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wailea-Makena vacation rentals

1. Aston Maui Hill

2. Grand Champions by KBM

3. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

4. Romantic 1 BR Condo with King Tempurpedic

5. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

6. Wailea Ekahi 29C, Ocean View, Steps away from the pool

7. Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC

8. Ekahi 27A: Priceless Ocean View from a Private Lanai

9. Luxury Condo on Wailea Blue Golf Course

10. Romantic, Luxury Maui Getaway with Ocean View - Couples Only

11. Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi

12. Wailea Ekahi Village WKV-45C by KBM

13. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

14. StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

15. Signature Residences at Maui Banyan

16. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

17. Romantic, Luxury, Sensual Retreat - Couples Only

18. Cozy, Well-Furnished Studio

19. Wailea Ekahi 24C, Summer in Paradise! Large 2 Bed 2 Bath, SLEEPS 6, beach access

20. Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!

Find vacation rentals that suit your style

Top Wailea-Makena Hotel Reviews

Four Seasons Resort Maui at Wailea

10/10 Excellent

Find out more about Wailea-Makena

Wailea-Makena vacation rentals: An excellent choice for every season

How to find incredible deals on Wailea-Makena rentals

Explore a world of travel with Expedia

13. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

14. StunningRenoPalms in Wailea Condo-BeachGolf*Pool