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

Holiday Homes in Wailea-Makena

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Wailea-Makena holiday homes

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.
The price is AU$816
includes taxes & fees
19 Sept - 20 Sept
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

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 AU$754
includes taxes & fees
19 Sept - 20 Sept
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

3. 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 AU$448
includes taxes & fees
29 Sept - 30 Sept
Yonegan Maui Getaways - Haiku

4. 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.
Villa 8

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 AU$651
includes taxes & fees
18 Sept - 19 Sept
Hale Nihi - Paia, Maui

6. Penthouse I

Penthouse I
South Kihei
10.0 out of 10, Exceptional, (19 reviews)
"Great place. Great location. "
United States
Lars B.
The price is AU$2,075
includes taxes & fees
23 Sept - 24 Sept
Penthouse I

7. Beach front Honu Cottage

Beach front Honu Cottage
South Kihei
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location with a private beach a few steps outside the back door. All kitchen essentials available and a bbq included. Perfect place to relax and beautiful scenery. "
United States
JESSICA S.
Beach front Honu Cottage

8. 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.
The price is AU$2,657
includes taxes & fees
6 Oct - 7 Oct
Plantation House

9. 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.
Penthouse II

10. 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 AU$1,507
includes taxes & fees
24 Sept - 25 Sept
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

11. 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 AU$698
includes taxes & fees
18 Sept - 19 Sept
HALE NIHI, Paia, Maui

12. 6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!

6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!
South Kihei
The price is AU$3,686
includes taxes & fees
14 Oct - 15 Oct
6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!

13. 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 AU$1,905
includes taxes & fees
30 Sept - 1 Oct
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

14. Kahili Suite - Historic charm meets Luxury

Kahili Suite - Historic charm meets Luxury
Wailuku
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful treasure of a property. My wife and I had an unexpected night in Wailuku and I'm so glad we found this inn. There were very few other people during our stay and we felt as though we had the property to ourselves. Pretty gardens, lovely spacious rooms. Great work on the renovation!"
United States
Scott H.
The price is AU$499
includes taxes & fees
18 Sept - 19 Sept
Kahili Suite - Historic charm meets Luxury

15. 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 AU$1,850
includes taxes & fees
16 Oct - 17 Oct
Maui Beach House

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

17. 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 AU$1,265
includes taxes & fees
18 Sept - 19 Sept
New! The Aloha Cottage in Puamana, Maui Hawaii

18. 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 AU$1,690
includes taxes & fees
20 Sept - 21 Sept
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

19. 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 AU$452
includes taxes & fees
23 Sept - 24 Sept
Mamane Suite - Historic charm and views

20. 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 AU$426
includes taxes & fees
18 Sept - 19 Sept
Romantic Maui Hideaway at The Historic Wailuku Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Wailea-Makena Hotel Reviews

Find out more about Wailea-Makena

Wailea-Makena Holiday Homes information

Number of reviews
759
Accommodation
64 Holiday Homes
Lowest Price
AU$426
Highest Price
AU$3,686