Wailea-Makena Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Wailea-Makena holiday rentals

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

1. Aston Maui Hill

South Kihei

Megan

HK$2,927 total

includes taxes & fees

6 Dec - 7 Dec

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

HK$8,200 total

includes taxes & fees

10 Nov - 11 Nov

A beach with clear turquoise water, sandy shore, and palm trees.

3. Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

Wailea

Amund N.

A beach with palm trees and a clear sky.

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

Wailea

Rojelio G.

HK$5,183 total

includes taxes & fees

8 Nov - 9 Nov

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

5. Romantic 1 BR Condo with King Tempurpedic

Wailea

Kathryn R.

HK$2,943 total

includes taxes & fees

18 Nov - 19 Nov

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

6. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

Wailea

Scott M.

HK$4,817 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Wailea

Petr K.

HK$7,502 total

includes taxes & fees

24 Nov - 25 Nov

A modern living room with a dining area, large windows, and decorative wall art.

8. Hawaiian Reno on Wailea Blue Golf Ocean ViewPool

Wailea

david k.

HK$3,768 total

includes taxes & fees

8 Nov - 9 Nov

A resort pool area with a view of the ocean and a golf course in the background.

9. DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

Wailea

Tim T.

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.

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

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

Wailea

Nick D.

HK$7,216 total

includes taxes & fees

4 Dec - 5 Dec

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

12. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

Wailea

Marcie M.

HK$4,034 total

includes taxes & fees

1 Dec - 2 Dec

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

13. Romantic, Luxury, Sensual Retreat - Couples Only

Wailea

Jessica N.

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

14. StunningRenoPalms in Wailea Condo-BeachGolf*Pool

Wailea

Emily B.

HK$4,035 total

includes taxes & fees

30 Nov - 1 Dec

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

15. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

Wailea

Darren P.

HK$7,540 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Wailea

Sandi G.

A round glass table set for four with wicker chairs, a view of the ocean, and tropical vegetation.

17. Polo Beach Club POL-109 by KBM

Wailea

"The property location was exactly what we wanted, easy access to the Wailea beachfront walking path and directly on the beach. We had a great time but if you are considering this place you need to go in with your eyes wide open. It was very pricey for how tired this unit is. It badly needs a full renovation. The tile is from the 1980's, the carpet is gross and crunchy. When we arrived late, it appeared someone had tried to break in the sliding doors and that set off numerous R&M emails...

PAMELA

HK$20,111 total

includes taxes & fees

6 Nov - 7 Nov

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

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

South Kihei

Paul B.

HK$4,655 total

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with clear blue water, surrounded by palm trees and lounge chairs.

19. Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq

Wailea

Anonymous traveller

A balcony with a view of a golf course, palm trees, and a mountain.

20. 514 - Oceanfront 2 bedroom Ocean View with A/C!

South Kihei

Allen M.

HK$5,003 total

includes taxes & fees

6 Nov - 7 Nov

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Top Wailea-Makena Hotel Reviews

Hotel Wailea Maui

10/10 Excellent

"This place was top tier. From the service to the cleanliness and aesthetics. Highly recommend!"

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."

Aston Maui Hill

8/10 Good

"We were traveling with 2 other couples. We all reserved 1 bedroom units. We were all upgraded to 2 or 3 bedroom units, which was nice but only two of us were in close proximity. We were near the bottom of the hill and the other couple was at the very top. It would have been nice if we could have all been together. The rooms were nice, the only complaint I have is the AC unit above the bed in the main bedroom was quite noisy. The staff was very friendly and we loved the full refrigerator and stocked kitchen. Having laundry in the unit was also great. The grounds were beautiful and it is easy to go down the stairs to get to the ocean. We were able to walk into town very easily. All in all, we all enjoyed our stay here. I was not prepared to have roosters waking me up at 6:40 but it was cool seeing all of the chickens all over the place."

Castle at Maui Banyan

8/10 Good

"Overall we had a wonderful stay as we visited on a family vacation with our 3 children. Staff were very friendly, pool was great, beautiful location! I will say though that the beds were horribly uncomfortable. My husband had to quite literally sleep on the couch cushions placed on the ground as the bed was extremely hard, shook constantly due to any movement. I slept on the bed with our baby and didn’t sleep well the entire week. This is the only issue we had as the matttess topper also was breaking apart if moved at all and looked extremely old and the mattress also appeared very old and stained. Other than this issue we did have a wonderful stay but I’m not sure if I would return due to this issue as we struggled with back pain from the beds. I also felt the pictures didn’t accurately portray the suite as all the photos showed beautiful big walk in showers however our was a tub. Overall not a big issue but felt a bit misleading."

Find out more about Wailea-Makena

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Maui Holiday Rentals

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wailea-Makena holiday rentals

1. Aston Maui Hill

2. Grand Champions by KBM

3. Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

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

5. Romantic 1 BR Condo with King Tempurpedic

6. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

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

8. Hawaiian Reno on Wailea Blue Golf Ocean ViewPool

9. DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

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

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

12. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

13. Romantic, Luxury, Sensual Retreat - Couples Only

14. StunningRenoPalms in Wailea Condo-BeachGolf*Pool

15. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

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

17. Polo Beach Club POL-109 by KBM

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

19. Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq

20. 514 - Oceanfront 2 bedroom Ocean View with A/C!

Find holiday rentals that suit your style

Top Wailea-Makena Hotel Reviews

Hotel Wailea Maui

Andaz Maui at Wailea Resort - a concept by Hyatt

Four Seasons Resort Maui at Wailea

Mana Kai Maui- Official Onsite Rental

Aston Maui Hill

Aston at the Maui Banyan

Wailea Beach Resort - Marriott, Maui

Castle at Maui Banyan

AC Hotel by Marriott Maui Wailea

Find out more about Wailea-Makena

Explore a world of travel with Expedia

Go further with the Expedia app

Wailea-Makena Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wailea-Makena holiday rentals

1. Aston Maui Hill

2. Grand Champions by KBM

3. Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach

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

5. Romantic 1 BR Condo with King Tempurpedic

6. #708 Wailea Ekolu - Spectacular Ocean View, Serene Setting

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

8. Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

9. DEAL $325 6/29-7/4 Gorgeous Walk to beach&pool! Contemporary Gem/Gallery/Bose

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

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

12. ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf

13. Romantic, Luxury, Sensual Retreat - Couples Only

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

15. 1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!

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

17. Polo Beach Club POL-109 by KBM

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

19. Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq

20. 514 - Oceanfront 2 bedroom Ocean View with A/C!

Find holiday rentals that suit your style

Top Wailea-Makena Hotel Reviews

Hotel Wailea Maui

Find out more about Wailea-Makena

Explore a world of travel with Expedia

Go further with the Expedia app

8. Hawaiian Reno on Wailea Blue Golf Ocean ViewPool

12. ContemporaryHawaiianReno in WaileaPoolBeach*Golf

14. StunningRenoPalms in Wailea Condo-BeachGolf*Pool