Wailea-Makena Vacation Rentals from $315: Search Short-Term Rentals

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Our top choices for Wailea-Makena vacation rentals

A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

1. Signature Residences at Maui Banyan

South Kihei

Mai

$510 nightly

Nov 23 - Nov 24

Total with taxes and fees

A beach with clear skies, calm sea, and a distant mountain.

2. 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.

$294 nightly

Nov 28 - Nov 29

Total with taxes and fees

3. Romantic 1 BR Condo with King Tempurpedic

Wailea

Linh H.

$307 nightly

Nov 20 - Nov 21

Total with taxes and fees

A spacious living room with a grey sofa, a coffee table, and a TV on the wall. There is a balcony with a view of the mountains.

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

Wailea

Matthew M.

$438 nightly

Dec 1 - Dec 2

Total with taxes and fees

A clear beach with visible pebbles and a mountain in the distance.

5. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

Wailea

Marcie M.

$441 nightly

Dec 1 - Dec 2

Total with taxes and fees

A beach with clear water, a sandy shore, and a building with a balcony overlooking the beach.

6. StunningRenoPalms in Wailea Condo-BeachGolf*Pool

Wailea

Nick F.

$441 nightly

Nov 30 - Dec 1

Total with taxes and fees

A golf course with a sunset view, palm trees, and a building with a sloped roof.

7. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

Wailea

Scott M.

$525 nightly

Nov 18 - Nov 19

Total with taxes and fees

A stone wall with a sign reading "Maui Hill" and a blue whale sculpture.

8. Aston Maui Hill

South Kihei

Megan

$265 nightly

Dec 14 - Dec 15

Total with taxes and fees

A beach with palm trees and a clear sky.

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

Wailea

Rojelio G.

$584 nightly

Nov 27 - Nov 28

Total with taxes and fees

A beach with a wooden staircase leading down to the shore, surrounded by greenery.

10. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

South Kihei

Lori D.

$442 nightly

Dec 1 - Dec 2

Total with taxes and fees

A beach with a sandy shore, clear blue water, and houses with red roofs in the background.

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

Wailea

Nick D.

$763 nightly

Dec 4 - Dec 5

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by tropical vegetation.

12. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

Wailea

lily v.

$492 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with people swimming and sunbathing, a rocky outcrop, and a distant mountain range.

13. Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View

Wailea

$581 nightly

Nov 19 - Nov 20

Total with taxes and fees

A beach with clear water, waves, and a distant mountain.

14. Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

South Kihei

Jody S.

$482 nightly

Dec 12 - Dec 13

Total with taxes and fees

An aerial view of a resort with a large pool, lounge chairs, and a small building.

15. Luxury Condo on Wailea Blue Golf Course

Wailea

Bryce

$588 nightly

Nov 30 - Dec 1

Total with taxes and fees

A spacious living area with a large sliding glass door leading to a balcony, a blue sofa, a wooden coffee table, and a kitchen area with a dining table and chairs.

16. Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

South Kihei

Jo

$342 nightly

Nov 14 - Nov 15

Total with taxes and fees

A sandy beach with footprints, a rocky shoreline, and a person in the distance.

17. Beautiful, Renovated, Hale Kamaole 159

South Kihei

Christopher

$305 nightly

Nov 19 - Nov 20

Total with taxes and fees

A beach with clear skies, calm waters, and distant mountains.

18. Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV

South Kihei

Terris S.

$465 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

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

South Kihei

Paul B.

$504 nightly

Nov 20 - Nov 21

Total with taxes and fees

A beach with a sunset, palm trees, and rocky shoreline.

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

Wailea

Roger B.

$543 nightly

Nov 17 - Nov 18

Total with taxes and fees

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Top Wailea-Makena Hotel Reviews

Days Inn by Wyndham Maui Oceanfront

10/10 Excellent

"Super clean and a few steps to the beach."

Andaz Maui at Wailea Resort - a concept by Hyatt

10/10 Excellent

"The most beautiful resort in Wailea! The rooms and resort were upscale and luxurious. It had a feeling of serenity compared to the other properties we walked through along the beach. We paid for the breakfast at time of booking which was a lower price in the package. The breakfast buffet was very good with lots of choices. I would definitely return to the Andaz."

AEI at Maui Banyan

8/10 Good

"We had a great stay! Although the condo complex is a little older, it was still very nice and had everything we needed. Having an in-unit washer and dryer was a huge plus, especially at the end of our trip. The front desk staff was very helpful and accommodating. We arrived quite early, and they were happy to hold our luggage until our room was ready. The location was probably one of the biggest advantages. There are several beaches in walking distance. There are also plenty of great restaurants, shopping options, and grocery stores within walking distance. Also an ABC store less than a 10 minute walk away. I would say that this is a great option if you don’t have a rental car. We were still able to check off several bucket-list activities and explore the area without needing a vehicle. Plus, Uber and Lyft were reasonably priced when we didn’t feel like walking. Overall, a great location and a solid option, especially for anyone visiting Maui without a car!"

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Wailea-Makena in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $315 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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Check prices for these dates

Our top choices for Wailea-Makena vacation rentals

1. Signature Residences at Maui Banyan

2. Cozy, Well-Furnished Studio

3. Romantic 1 BR Condo with King Tempurpedic

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

5. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

6. StunningRenoPalms in Wailea Condo-BeachGolf*Pool

7. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

8. Aston Maui Hill

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

10. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

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

12. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

13. Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View

14. Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

15. Luxury Condo on Wailea Blue Golf Course

16. Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

17. Beautiful, Renovated, Hale Kamaole 159

18. Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV

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

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

Find vacation rentals that suit your style

Top Wailea-Makena Hotel Reviews

Days Inn by Wyndham Maui Oceanfront

Fairmont Kea Lani Maui

Aston at the Maui Banyan

Wailea Ekahi - CoralTree Residence Collection

Mana Kai Maui- Official Onsite Rental

Wailea Beach Resort - Marriott, Maui

Castle at Maui Banyan

Andaz Maui at Wailea Resort - a concept by Hyatt

AEI at Maui Banyan

Find out more about Wailea-Makena

Explore a world of travel with Expedia

Expedia's Latest Trends

Wailea-Makena Vacation Rentals

Check prices for these dates

Our top choices for Wailea-Makena vacation rentals

1. Signature Residences at Maui Banyan

2. Cozy, Well-Furnished Studio

3. Romantic 1 BR Condo with King Tempurpedic

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

5. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

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

7. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

8. Aston Maui Hill

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

10. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

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

12. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

13. Palms at Wailea 406 Spacious Condo, Large Lanai, A/C, Partial Ocean View

14. Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach

15. Luxury Condo on Wailea Blue Golf Course

16. Across From Kamaole 2 Beach, This Concrete Resort Is Maintained Well

17. Beautiful, Renovated, Hale Kamaole 159

18. Walk to Beach Kamaole Sands Inner Courtyard, Ground Floor, Smart TV

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

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

Find vacation rentals that suit your style

Top Wailea-Makena Hotel Reviews

Days Inn by Wyndham Maui Oceanfront

Find out more about Wailea-Makena

Explore a world of travel with Expedia

Expedia's Latest Trends

5. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

6. StunningRenoPalms in Wailea Condo-BeachGolf*Pool