Vacation Rentals in Wailea
Start comparing over 1,886 rentals in Wailea and book at the best price!
Find offers
Vacation rentals with pets allowed
Pets allowed
2 bedrooms
8.3
Pets allowed
2 bedrooms
9.9
Pets allowed
4 bedrooms
9.4
Pets allowed
3 bedrooms
8.8
Vacation Rentals in Wailea
1 bedroom
9.2
1 bedroom
9.7
1 bedroom
9.1
2 bedrooms
9.1
Vacation rentals in city center
1 bedroom
9.4
2 bedrooms
10.0
1 bedroom
9.8
1 bedroom
9.0
Vacation rentals with free cancellation
1 bedroom
9.6
1 bedroom
8.1
1 bedroom
8.6
2 bedrooms
9.8
Child-friendly vacation rentals
1 bedroom
9.7
1 bedroom
7.0
2 bedrooms
from $188 / nightFREE cancellation
2 bedrooms
from $150 / nightFREE cancellationFind Vacation Rentals in Wailea
Best Vacation Rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.
more...
Keawakapu, Wailea
Vacation Rental • 1109 ft² • 3 Bedrooms
Keawakapu, Wailea
10.0
Hosted by VacaMauiWe chose Hale Kamaole due to it's fantastic location directly across the street from Kamaole Beach Park 3. Kamaole 3 is a beautiful white sand beach which is popular for swimming, snorkeling, and boogie boarding. The unit was finished being completely remodeled from top to bottom in July 2022. Vaulted ceilings throughout, stainless steel appliances, air conditioning, quartz countertops, and a 65" TV are some of the amenities you will enjoy during your stay.The unit is on the second floor and does not have an elevator. It is steps to the beach. The back lanai has a fantasti...
from $194 / night
View offer
more...
Keawakapu, Wailea
Vacation Rental • 1109 ft² • 3 Bedrooms
Keawakapu, Wailea
Hosted by VacaMauiWe chose Hale Kamaole due to it's fantastic location directly across the street from Kamaole Beach Park 3. Kamaole 3 is a beautiful white sand beach which is popular for swimming, snorkeling, and boogie boarding. The unit was finished being completely remodeled from top to bottom in September 2023. Vaulted ceilings throughout, stainless steel appliances, air conditioning, quartz countertops, and a 75" TV are some of the amenities you will enjoy during your stay.The unit is on the third floor and has an elevator. It is steps to the beach. It is a short walk from either of t...
from $194 / night
View offer
more...
Keawakapu, Wailea
Vacation Rental • 1109 ft² • 2 Bedrooms
Keawakapu, Wailea
9.7
Hosted by VacaMauiWe chose Hale Kamaole due to it's fantastic location directly across the street from Kamaole Beach Park 3. Kamaole 3 is a beautiful white sand beach which is popular for swimming, snorkeling, and boogie boarding. Vaulted ceilings throughout, stainless steel appliances, air conditioning, quartz countertops, and a 65" TV are some of the amenities you will enjoy during your stay.The unit is on the second floor directly across the street from Kamaole Beach 3. We love having meals on the covered lanai. Some of the features of the condo include:- Hale Kamaole: Building #5 , Unit...
from $314 / night
View offer
Prices and availability
FAQs: Vacation Rentals in Wailea
What is the average price for vacation rentals in Wailea?
Based on last year, Wailea had an average price of $467 per night, a relatively high one compared to the cities in the USA.
During which months can you find the best price for vacation rentals in Wailea?
]If you want to get the most out of your money, the most budget-friendly months to visit Wailea are August ($389 the average per night for accommodation), May ($389), and June ($406).
In which months is it more expensive to rent a vacation rental in Wailea?
When it comes to looking for a vacation rental in Wailea, the months that cost the most are, in order of highest to lowest, February, January and March, with average prices per night of $631, $584, and $560, respectively.
Is Wailea a good location for a last-minute getaway?
It is better to book your stay with plenty of time when visiting Wailea, as only 12% of our properties are usually available throughout the year.
What time of the year can I find more available vacation rentals?
Last year, the months with the largest number of properties available of the year in Wailea were May, October and September, with average availabilities of 37%, 17%, and 17%, respectively.
When will it be harder to find an available vacation rental in Wailea?
The month with the highest average booked rental figures is February (only 3% of properties were available on average last year). Followed by March (5%), and then January (5%). During these three months, the availability is only 5%. It is therefore preferable to reserve far in advance.
How many rentals are there in Wailea?
In Wailea we offer you a comprehensive catalog of around 320 properties, with options of all kinds, thanks to our 6 local and international providers.