A coastal landscape with rocky cliffs, a body of water, and a distant mountain range under a cloudy sky.

Holiday Homes in Wailea-Makena

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wailea-Makena holiday homes

A beach with clear blue water, a sandy shore, and greenery.

1. Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
South Kihei
9.2 out of 10, Wonderful, (63 reviews)
"Our vacation was amazing! The place was even better than we expected — super clean, cozy, and had everything we needed in the kitchen. The AC worked great, and the view from the patio was just beautiful. The beach is right across the street and honestly one of the best around. We already know where we’ll stay next time — we loved it!"
United States
Olga T.
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

2. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is NZ$882
includes taxes & fees
30 Sept - 1 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
An outdoor lounge area with wooden furniture and green cushions, a pool, and a view of the surrounding greenery.

3. Villa 8

Villa 8
South Kihei
9.8 out of 10, Exceptional, (74 reviews)
"staying here was the best! perfect for our anniversary get away!"
United States
Taylor M.
The price is NZ$1,204
includes taxes & fees
7 Oct - 8 Oct
Villa 8
A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

4. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is NZ$530
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

5. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is NZ$827
includes taxes & fees
30 Sept - 1 Oct
Hale Nihi - Paia, Maui
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

6. HALE NIHI, Paia, Maui

HALE NIHI, Paia, Maui
Paia
9.6 out of 10, Exceptional, (106 reviews)
"great location, great host"
United States
Peter M.
The price is NZ$887
includes taxes & fees
2 Oct - 3 Oct
HALE NIHI, Paia, Maui
A wooden fence with a sign reading "WOODSTOCK" and a peace sign.

7. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (110 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is NZ$1,997
includes taxes & fees
30 Sept - 1 Oct
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
A spacious living room with a piano, wicker furniture, and a large mirror.

8. Pikake Suite - Historic Elegance, Wailuku

Pikake Suite - Historic Elegance, Wailuku
Wailuku
10.0 out of 10, Exceptional, (9 reviews)
"Easy parking"
United States
Quinten M.
The price is NZ$521
includes taxes & fees
30 Sept - 1 Oct
Pikake Suite - Historic Elegance, Wailuku
A modern bedroom with a large bed, a wooden bench, and a tray with breakfast items.

9. Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Lori R.
The price is NZ$2,377
includes taxes & fees
30 Sept - 1 Oct
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
A swimming pool with lounge chairs and palm trees.

10. Penthouse II

Penthouse II
South Kihei
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful stay in a desirable location! We absolutely loved it! "
United States
Lindsay T.
The price is NZ$2,603
includes taxes & fees
4 Oct - 5 Oct
Penthouse II
A swimming pool with lounge chairs and palm trees.

11. Penthouse I

Penthouse I
South Kihei
10.0 out of 10, Exceptional, (19 reviews)
"Great place. Great location. "
United States
Lars B.
Penthouse I
An outdoor lounge area with wooden furniture and green cushions, a pool, and a view of the surrounding garden.

12. Plantation House

Plantation House
South Kihei
10.0 out of 10, Exceptional, (62 reviews)
"Everything was excellent! We had a great experience—very clean property in a fantastic location with great beach amenities. Would absolutely stay here againm!"
United States
Kristi G.
Plantation House
A two-story wooden house with a balcony, surrounded by lush greenery and palm trees.

13. Maui Beach House

Maui Beach House
Central Kihei
10.0 out of 10, Exceptional, (46 reviews)
"My family and I had a wonderful time at this beach house. The host is very responsive in a timely manner. We loved the location, and enjoyed the beach everyday. The description is accurate and we will be staying here again. "
United States
MaRee C.
The price is NZ$2,476
includes taxes & fees
16 Oct - 17 Oct
Maui Beach House
A swimming pool with lounge chairs and palm trees.

14. 6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!

6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!
South Kihei
6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!
A modern kitchen with a large island, pendant lighting, and a view of greenery outside.

15. New! The Aloha Cottage in Puamana, Maui Hawaii

New! The Aloha Cottage in Puamana, Maui Hawaii
Lahaina
9.8 out of 10, Exceptional, (100 reviews)
"Excellent quiet location in a HOA neighborhood, two pools one on the lake. Just beyond where the fires hit years ago as they’re just starting to rebuild, but this unit and that half of the neighborhood was spared. Nicely remodeled on the inside."
United States
Jason D.
The price is NZ$1,612
includes taxes & fees
30 Sept - 1 Oct
New! The Aloha Cottage in Puamana, Maui Hawaii
A beachfront property with a house surrounded by palm trees and a sandy beach.

16. Oceanfront Hideaway

Oceanfront Hideaway
Central Kihei
9.8 out of 10, Exceptional, (16 reviews)
"A beautiful home in a great location on the beach. Perfect for our family vacation. "
United States
Emily S.
Oceanfront Hideaway
A coastal property with a house, a covered patio, and a view of the ocean.

17. Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC
Lahaina
10.0 out of 10, Exceptional, (8 reviews)
"Such a great location, everything we possibly needed, clean, easy & clear check in, beautiful decor and especially enjoyed the easy access to the beach for sunset. "
United States
Stephanie T.
The price is NZ$2,180
includes taxes & fees
30 Sept - 1 Oct
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC
A spacious living room with a piano, a dining area with wicker chairs, and a large window.

18. Elegant Puakenikeni Suite- Historic & Ground Floor

Elegant Puakenikeni Suite- Historic & Ground Floor
Wailuku
10.0 out of 10, Exceptional, (7 reviews)
"I liked the quaint ambiance of the property, beautiful landscape and the room was great."
United States
Wayne
The price is NZ$592
includes taxes & fees
30 Sept - 1 Oct
Elegant Puakenikeni Suite- Historic & Ground Floor
A spacious living room with a piano, wicker furniture, and a large mirror.

19. Romantic Maui Hideaway at The Historic Wailuku Inn

Romantic Maui Hideaway at The Historic Wailuku Inn
Wailuku
10.0 out of 10, Exceptional, (3 reviews)
"Loved this B&B. The location worked well from exploring different areas. Will stay here again."
United States
Arthur C.
The price is NZ$555
includes taxes & fees
30 Sept - 1 Oct
Romantic Maui Hideaway at The Historic Wailuku Inn
A spacious living room with a piano, a dining area with wicker chairs, and a large window.

20. Mamane Suite - Historic charm and views

Mamane Suite - Historic charm and views
Wailuku
10.0 out of 10, Exceptional, (5 reviews)
"This was my 2nd time staying here and I love it. Super nice rooms, yummy breakfast."
United States
Jane D.
The price is NZ$653
includes taxes & fees
6 Oct - 7 Oct
Mamane Suite - Historic charm and views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wailea-Makena Hotel Reviews

Days Inn by Wyndham Maui Oceanfront

Days Inn by Wyndham Maui Oceanfront

10/10 Excellent
"Didn’t know what to expect, having never stayed at this particular Days Inn before, but they exceeded our expectations! Loved the beach chairs and towels in the room, and having a mini fridge and microwave in a standard room. Breakfast was light but just right. Great value here! Thank you.."
Carolyn 1-night trip
Posted 21 hours ago
Days Inn by Wyndham Maui Oceanfront

Find out more about Wailea-Makena

Wailea-Makena Holiday Homes information

Number of reviews
756
Accommodation
64 Holiday Homes
Lowest Price
NZ$521
Highest Price
NZ$2,603

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