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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Wailea-Makena holiday homes

Exterior

1. Kamaole Sands 3104-Bright and Fresh!

Kamaole Sands 3104-Bright and Fresh!
South Kihei
10.0 out of 10, Exceptional, (51 reviews)
"Beautiful and comfortable ground unit in a great Kihei complex."
United States
Shaun C.
The price is NZ$810
includes taxes & fees
28 Aug - 29 Aug
Kamaole Sands 3104-Bright and Fresh!
Sun-loungers, beach towels

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$813
includes taxes & fees
23 Aug - 24 Aug
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Studio, Garden View (Haiku #6) | Terrace/patio

3. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (36 reviews)
"Large room and bathroom. Nice little kitchen area. We had a room with two balconies so great air flow through to cool the room. Beautiful area of Hawaii to explore"
Canada
Amanda
The price is NZ$509
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku
Exterior detail

4. 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, (111 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is NZ$1,690
includes taxes & fees
16 Aug - 17 Aug
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
On the beach

5. Beach front Honu Cottage

Beach front Honu Cottage
South Kihei
9.4 out of 10, Exceptional, (9 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.
The price is NZ$1,888
includes taxes & fees
24 Aug - 25 Aug
Beach front Honu Cottage
Pool

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 NZ$2,473
includes taxes & fees
16 Aug - 17 Aug
Penthouse I
Pool

7. 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$2,525
includes taxes & fees
16 Aug - 17 Aug
Penthouse II
4 bedrooms, in-room safe, blackout curtains, iron/ironing board

8. 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)
"The house is an easy walk to a quiet beach and any easy drive to a grocery store and restaurants. The house was clean and well stocked. "
United States
Kimberly F.
The price is NZ$2,209
includes taxes & fees
23 Aug - 24 Aug
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
Terrace/patio

9. 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 NZ$2,662
includes taxes & fees
22 Aug - 23 Aug
Plantation House
Interior

10. 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$649
includes taxes & fees
31 Aug - 1 Sept
Pikake Suite - Historic Elegance, Wailuku
Sun-loungers, beach towels

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 NZ$937
includes taxes & fees
26 Aug - 27 Aug
HALE NIHI, Paia, Maui
Beach nearby, sun-loungers, beach towels

12. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (64 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is NZ$937
includes taxes & fees
26 Aug - 27 Aug
Hale Nihi - Paia, Maui
On the beach

13. Oceanfront Hideaway

Oceanfront Hideaway
Central Kihei
9.8 out of 10, Exceptional, (15 reviews)
"A beautiful home in a great location on the beach. Perfect for our family vacation. "
United States
Emily S.
The price is NZ$4,652
includes taxes & fees
26 Aug - 27 Aug
Oceanfront Hideaway
Coffee/tea maker, fridge, microwave, oven

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

New! The Aloha Cottage in Puamana, Maui Hawaii
Lahaina
9.8 out of 10, Exceptional, (99 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$1,516
includes taxes & fees
16 Aug - 17 Aug
New! The Aloha Cottage in Puamana, Maui Hawaii
Pool

15. 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 NZ$4,600
includes taxes & fees
16 Aug - 17 Aug
6 Bedroom, 6 Bathroom Maui Oasis at Villas by the Cove!
Property grounds

16. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (7 reviews)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
The price is NZ$1,446
includes taxes & fees
17 Aug - 18 Aug
Haiku Hale - 3 Bedroom Maui Getaway!
Interior

17. 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$579
includes taxes & fees
30 Aug - 31 Aug
Elegant Puakenikeni Suite- Historic & Ground Floor
Interior

18. Lehua Suite - Hawaiian elegance | Patio garden

Lehua Suite - Hawaiian elegance | Patio garden
Wailuku
10.0 out of 10, Exceptional, (2 reviews)
"Thank you for a wonderful stay. Our suite was great and comfortable. We well truly be back."
United States
JoAnn H.
The price is NZ$679
includes taxes & fees
31 Aug - 1 Sept
Lehua Suite - Hawaiian elegance | Patio garden
Terrace/patio

19. Island Views Oceanfront 2 Master Bedrooms, Cold AC

Island Views Oceanfront 2 Master Bedrooms, Cold AC
Lahaina
10.0 out of 10, Exceptional, (33 reviews)
"Fantastic location and great communication from Kevin! We thoroughly enjoyed our stay!!"
United States
Janelle G.
The price is NZ$2,609
includes taxes & fees
1 Sept - 2 Sept
Island Views Oceanfront 2 Master Bedrooms, Cold AC
Exterior

20. 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$2,331
includes taxes & fees
18 Aug - 19 Aug
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wailea-Makena Hotel Reviews

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"Great for families only thing seating can be improved with a lot of people, hard to find seating not impossible had a great time with the family had a amazing time with the shops 2 mins away (walking) it’s a big plus"
Ricardo 6-night trip
Posted 12 hours ago
Wailea Beach Resort - Marriott, Maui

Find out more about Wailea-Makena

Wailea-Makena Holiday Homes information

Number of reviews
719
Accommodation
70 Holiday Homes
Lowest Price
NZ$509
Highest Price
NZ$4,652

Explore a world of travel with Expedia