Vacation Rentals in Wailea
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Vacation rentals in Wailea
Wailea, Maui
Vacation rental for 6 people, with pool and balcony, kid friendly
Free cancellation
from $239 per night
Wailea, Maui
Vacation rental for 4 people, with pool and balcony, kid friendly
Free cancellation
from $121 per night
Wailea, Maui
Vacation rental for 4 people, with balcony and pool, kid friendly
Free cancellation
from $287 per night
Wailea, Maui
Vacation rental for 4 people, with terrace and pool
Free cancellation
from $105 per night
Vacation rentals in city center
Wailea, Maui
Vacation rental for 4 people, with yard and balcony as well as pool, kid friendly
Free cancellation
from $314 per night
Wailea, Maui
9.9
Vacation rental for 4 people, with hot tub and pool as well as balcony
Free cancellation
from $410 per night
Wailea, Maui
9.7
Vacation rental for 4 people, with hot tub and pool as well as terrace
Free cancellation
from $577 per night
Keawakapu, Wailea
9.5
Vacation rental for 5 people, with terrace and yard
Free cancellation
from $635 per night
Vacation rentals with free cancellation
Maui Meadows, Wailea
9.9
Vacation rental for 4 people, with pool and terrace as well as yard
Free cancellation
from $550 per night
Wailea, Maui
9.0
Vacation rental for 4 people, with pool and yard
Free cancellation
from $422 per night
Wailea, Maui
9.9
Vacation rental for 10 people, with balcony and sauna as well as pool
Free cancellation
from $1,917 per night
Wailea, Maui
9.9
Vacation rental for 2 people, with hot tub and balcony as well as yard
Free cancellation
from $382 per night
Vacation Rentals with Pool
Wailea, Maui
9.9
Vacation rental for 8 people, with hot tub and pool as well as yard
from $2,333 per night
Maui Meadows, Wailea
9.9
Vacation rental for 4 people, with yard
Free cancellation
from $605 per night
Keawakapu, Wailea
9.6
Vacation rental for 6 people, with pool and yard as well as balcony
Free cancellation
from $440 per night
Keawakapu, Wailea
9.5
Vacation rental for 6 people, with hot tub and yard as well as pool
Free cancellation
from $414 per night
Child-friendly vacation rentals
Wailea, Maui
8.3
Vacation rental for 4 people, with balcony and pool, kid friendly
Free cancellation
from $118 per night
Wailea, Maui
Vacation rental for 4 people, with pool and balcony, kid friendly
Free cancellation
from $154 per night
Wailea, Maui
Vacation rental for 4 people, with balcony and pool, kid friendly
Free cancellation
from $124 per night
Wailea, Maui
Vacation rental for 4 people, with balcony and pool, kid friendly
Free cancellation
from $56 per night
Find Vacation Rentals in Wailea
Best Vacation Rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Wailea, Maui
Vacation Rental • 4 Guests • 1 Bedroom
Wailea, Maui
Welcome to Your Maui Escape! Step inside this stylish, open-concept retreat designed for relaxation. The Space: ️ Spacious & modern living area w/ HDTV ☕ Fully-equipped kitchen w/ premium appliances Private lanai w/ seating & garden views ️ King bedroom w/ plush mattress & Smart TV ️ Memory foam sofa bed – Comfort for extra guests Spa-like bathroom w/ granite vanity & rainfall shower AC & ceiling fans throughout for optimal comfort Prime Location: ✔️ 5-min walk to Charley Young & Kamaole II Beach ✔️ Steps from local dining, shopping & nightlife ✔️ Short drive to ...
from $105 / night
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Wailea, Maui
Vacation Rental • 4 Guests • 1 Bedroom
Wailea, Maui
Welcome to Maui! Nestled in a peaceful resort community, this stylish retreat offers everything you need for a memorable stay. ️ Bedroom: King-size bed w/ premium linens for a restful sleep. ️ Living Area: Comfy sofa, dining space & large Smart TV. Private Balcony: Enjoy fresh breezes & lush tropical views. Bathroom: Modern shower/tub combo w/ high-end toiletries. ️ Kitchenette: Mini-fridge, microwave & essentials for light meals. A/C & Ceiling Fans: Stay cool & comfortable all day. Resort Perks: Sparkling pool, hot tub, BBQ grills & tennis courts. Location Highlight...
from $121 / night
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Wailea, Maui
Vacation Rental • 4 Guests • 1 Bedroom
Wailea, Maui
Welcome to Maui! This stylish 1BR/1BA condo blends modern comfort with tropical charm. Inside the Space: ️ King Suite + Premium Sofa Bed – Relax in plush comfort ️ Open Living Space – Designed for relaxation & connection Fully-Stocked Kitchen – Includes stove, oven, microwave, dishwasher, & more Luxe Bathroom – Spacious shower & premium amenities 82” & 65” Smart TVs – Netflix & cable ready In-Unit Washer & Dryer – Hassle-free stays Outdoor Perks: Private Lanai – Overlooks a serene poolside setting Beach Gear – Chairs, umbrellas & cooler included Resort-Style Pool...
from $287 / night
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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.