Search Wailea-Makena Cottage Rentals

  • 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

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Wailea-Makena cottages

1. Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops
Central Kihei
10.0 out of 10, Exceptional, (80 reviews)
"RENT HERE! Not only it is the cutest place, its super clean,private as can be, high end everything, and close to everything. We also love the EASY contact-less check-in...and it was flexible with time since we got in late. The hottub is the icing on top :) 10/10"
United States
Gretchen G.
The price is ¥50,468
¥94,966 total
includes taxes & fees
Nov 28 - Nov 29
Luxury cottage, private, saltwater spa🌺walk to beach, dining,shops

2. Adorable 1930's Gingerbread House....Permitted!

Adorable 1930's Gingerbread House....Permitted!
Makawao
9.8 out of 10, Exceptional, (13 reviews)
"a beautiful property and a nice cottage! We completely enjoyed our time here."
United States
Kathy W.
The price is ¥39,528
¥88,969 total
includes taxes & fees
Nov 16 - Nov 17
Adorable 1930's Gingerbread House....Permitted!

3. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is ¥91,514
¥198,860 total
includes taxes & fees
Nov 30 - Dec 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean 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.

Learn more about Wailea-Makena

Discover things to see and do in Wailea-Makena as you venture to popular sights like Wailea Beach.

A wooden sign for Keawa'i Church with a stone building and palm trees in the background.

Top reviews in Wailea-Makena

Explore a world of travel with Expedia