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

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Our top choices for Wailea-Makena holiday rentals

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

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

Wailea

Matthew M.

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

2. Romantic 1 BR Condo with King Tempurpedic

Wailea

Kathryn R.

HK$3,131 total

includes taxes & fees

18 Nov - 19 Nov

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

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

South Kihei

Paul B.

HK$4,654 total

includes taxes & fees

10 Nov - 11 Nov

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

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

Wailea

Tim T.

HK$5,076 total

includes taxes & fees

15 Nov - 16 Nov

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

5. Signature Residences at Maui Banyan

South Kihei

Mai

HK$4,496 total

includes taxes & fees

4 Nov - 5 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

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

7. Aston Maui Hill

South Kihei

Megan

HK$2,717 total

includes taxes & fees

3 Dec - 4 Dec

A balcony with a view of a golf course, a table with chairs, and a small air conditioning unit.

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

Wailea

lily v.

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

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

Wailea

Petr K.

HK$5,000 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Wailea

Rojelio G.

HK$5,210 total

includes taxes & fees

8 Nov - 9 Nov

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

11. Hawaiian Reno on Wailea Blue Golf Ocean ViewPool

Wailea

david k.

HK$3,768 total

includes taxes & fees

8 Nov - 9 Nov

A resort with a well-maintained garden, palm trees, and a view of the ocean.

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

South Kihei

Jody S.

HK$4,294 total

includes taxes & fees

4 Nov - 5 Nov

A swimming pool area with lounge chairs and a covered patio.

13. Beautiful Ocean View Studio!

South Kihei

Susan C.

HK$3,180 total

includes taxes & fees

4 Nov - 5 Nov

A resort with a view of the sunset over the ocean, palm trees, and a well-maintained lawn.

14. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

South Kihei

Lori D.

HK$4,278 total

includes taxes & fees

1 Dec - 2 Dec

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

15. Grand Champions by KBM

Wailea

Sean

HK$7,229 total

includes taxes & fees

19 Nov - 20 Nov

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

South Kihei

Terris S.

HK$4,323 total

includes taxes & fees

11 Nov - 12 Nov

A view of tall palm trees against a cloudy sky.

17. One Bedroom Ocean View

South Kihei

Patricia

HK$3,503 total

includes taxes & fees

1 Dec - 2 Dec

A tropical garden with palm trees, a lawn, and a view of the ocean.

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

Wailea

Amund N.

HK$5,650 total

includes taxes & fees

10 Nov - 11 Nov

A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

19. The Residences at Kamaole Sands Resort

South Kihei

George Lucas

HK$5,472 total

includes taxes & fees

5 Nov - 6 Nov

A balcony with a view of a sunset over palm trees and a row of modern buildings.

20. Beautiful, Renovated, Hale Kamaole 159

South Kihei

Christopher

HK$2,899 total

includes taxes & fees

12 Nov - 13 Nov

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Top Wailea-Makena Hotel Reviews

Andaz Maui at Wailea Resort - a concept by Hyatt

10/10 Excellent

"Amazing"

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."

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!"

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Check prices for these dates

Our top choices for Wailea-Makena holiday rentals

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

2. Romantic 1 BR Condo with King Tempurpedic

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