Wailea Vacation Rentals - HolidayHomes base64Hash Wailea Vacation Rentals - HolidayHomes

Wailea Vacation Rentals

Browse 7,029 available vacation homes and compared across 29 trusted partners

Anytime
Guests
Anytime
Guests

Top-Rated Vacation rentals in Wailea

Book the highest-rated Wailea vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Wailea
Sale! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views
Book now
Condo Wailea
Condo with heated pool & jacuzzi | Nature view
Book now
Condo Wailea
Maui Parkshore 410 - Modern Renovation & Stunning Ocean Views, Kamaole III Beach
Book now
Condo Wailea
Family-oriented condo with patio, pool & yard | Nature view | Next to the beach
Book now
Villa Wailea
Fully equipped villa with sauna, pool & hot tub | Next to the beach
Book now
House Wailea
Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole Home
Book now
Condo Wailea
Condo with barbeque & pool | Beach view
Book now
Condo Wailea
Summer Deal Wailea Golf Course Condo with Pool and Lanai Views
Book now
Condo Wailea
Wrap-Around Beach & Ocean Views Polo Beach 301
Book now
Condo Wailea
Condo with pool
Book now
Condo Wailea
Condo with pool & grill | Beach view
Book now
Condo Wailea
Condo with terrace, BBQ & pool | Nature view | Suitable for remote work
Book now
Condo Wailea
Condo with pool, yard & grill | Water view
Book now
Condo Wailea
Condo with pool & BBQ
Book now
Villa Wailea
Family-oriented villa with pool, patio & jacuzzi | Beach nearby
Book now

Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 7,029 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with terrace, pool & grill | Nature view | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
This spacious 6-person condo in Wailea features a beautiful balcony with stunning views and easy beach access.
from $321
per night
(116)
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with hot tub, BBQ & garden | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This spacious 6-person condo in Wailea features a heated pool and offers a perfect retreat for families and friends.
from $765
per night
(32)
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly lovely condo with garden, sauna & barbecue | Beach nearby | Perfect for remote work

Wailea, Wailea-Makena, Hawaii, United States
This spacious 6-person condo in Kihei features a relaxing balcony with ocean views and easy access to nearby beaches.
from $263
per night
(27)
View deal
Villa Wailea
Villa ∙ 6 guests ∙ 3 bedrooms

Fully equipped villa with sauna, terrace & grill | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This elegant villa in Wailea accommodates 6 guests and features a stunning heated pool for relaxation and enjoyment.
from $1,273
per night
(54)
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with barbeque, pool & jacuzzi | Water view

Wailea, Wailea-Makena, Hawaii, United States
This spacious 8-person condo in Wailea features a stunning sea view and offers beach access for a perfect getaway.
from $550
per night
(66)
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with heated pool & barbeque | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo accommodates 6 guests and features a balcony ideal for enjoying the beautiful surroundings.
from $286
per night
(11)
View deal
House Wailea
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace, yard & barbecue | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $716
per night
(18)
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, pool & garden | City view

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo accommodates 6 guests and features convenient beach access for a perfect getaway.
from $391
per night
(8)
View deal
House Wailea
House ∙ 12 guests ∙ 4 bedrooms

Vacation home with yard, terrace & private pool | Mountain view | Perfect for remote work

Wailea, Wailea-Makena, Hawaii, United States
This house rental in Wailea accommodates 12 guests and features a private pool for relaxation and enjoyment.
from $1,760
per night
(98)
View deal

More travel options

image-tag