Whether you choose a condo or villa as your Wailea vacation rental, you'll have the perfect base to explore the beauty of Maui.

Choose the perfect vacation rental
Best Vacation Home Deals in Wailea
Save up to 29%
Compare and find the perfect vacation rental from $359 per night by exploring the 4,778 properties available in Wailea. By comparing these vacation rentals, HomeToGo brings you the best deals and the highest rated accommodations in Wailea.
Top-Rated Offers and Accommodations in Wailea
Book Vacation Rentals with the Highest User Rating
Recommended Vacation Rentals in Wailea
Find your perfect vacation rental in Wailea: from $227 per night
Budget-friendly Rentals in Wailea
Find Fantastic yet Inexpensive Rentals
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Wailea and book a vacation rental with air conditioning.
Apartments with a balcony or patio
Looking for a home with a balcony? Check out these vacation homes in Wailea with their own private patios and balconies.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Wailea rental with full kitchen.
Popular Rental Amenities in Wailea
Wailea is a wonderful vacation destination if you want a rental with a pool, as 92% of the properties there provide one. Condo with pools in Wailea are a great option for groups of 5 and cost, on average, $1,192 per night. In Wailea, many of the properties with a pool are close to the water.
Price and Availability Index in Wailea
Vacation Rental Price Information in Wailea
The graph shows average prices of rentals in Wailea for the next twelve months. The most expensive prices are in February (2/10 – 2/17). Prices reach an average of $1,128 per night. However, in September (9/21 – 9/28), prices decrease to an average of $689 per night.
Rental availability information in Wailea
The availability graph shows the percentage of available rentals in Wailea. So far, the week with the least available rentals in Wailea is in December (12/23 – 12/30). August (8/31 – 9/7) has got the highest percentage of available rentals.
The Weather in Wailea
Find the Wailea climate diagram. On average, the warmest month is August. Conversely, January is the coolest month in Wailea, with temperatures going under 17° March is the wettest month.
7-Day Weather Forecast in Wailea
Information about vacation rentals in Wailea
🏡 Vacation rentals available | 4,778 homes |
---|---|
💳 Possible discounts | up to 34% |
🌙 Nightly prices starting at | $359 |
⭐ Popular amenities | Pool, Internet and Air conditioning |
🏊 Vacation rentals with pools | 4,409 homes |
Frequently Asked Questions
What is the typical price of a vacation home in Wailea?
Accommodation prices in Wailea start at $359 per night.
What is the typical availability of House rental in Wailea?
August has the highest availability of House rental in Wailea, so you can expect plenty of selection, even for last-minute bookings.
What are the most popular vacation home amenities in Wailea?
Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Wailea.
How many House rental and Apartment rental can I find in Wailea?
Wailea has 4,778 House rental and Apartment rental available to book.
Are there pet-friendly vacation rentals in Wailea?
Yes, there are 46 pet-friendly vacation rentals in Wailea, with an average nightly price of $2,885.
What's the best month to visit Wailea?
When booking accommodation in Wailea, remember that the rainiest months are usually March and November, with January often being the sunniest.
We list offers from thousands of providers, including












Top cities to visit
- Orlando Vacation Rentals
- Orleans Vacation Rentals
- Myrtle Beach Vacation Rentals & Condos
- San Francisco Vacation Rentals
- Miami Vacation Rentals
- San Diego Vacation Rentals
- Phoenix Condos & Vacation Rentals
- Kissimmee Vacation Rentals
- Brentwood Vacation Rentals
- Chicago Condo Rentals
- Key West Vacation Rentals
- Virginia Beach Vacation Rentals
- Clearwater, FL Vacation Rentals
- Edgewater Vacation Rentals
Vacation Destinations Near Wailea
-
Kihei Vacation Rentals
-
Kahului Vacation Rentals
-
Lahaina Vacation Rentals
-
Kaanapali Vacation Rentals
-
Kahana Vacation Rentals
-
Kapalua Vacation Rentals
-
Kaunakakai Vacation Rentals
-
Hawi Vacation Rentals
-
Hapuna Beach Vacation Rentals
-
Waikoloa Village Vacation Rentals
-
Kohala Vacation Rentals
-
Honokaa Vacation Rentals
-
Holualoa Vacation Rentals
-
Waimanalo Vacation Rentals
-
Kailua Vacation Rentals
-
Honolulu Vacation Rentals
-
Ewa Beach Vacation Rentals
-
Waipahu Vacation Rentals
-
Kapolei Vacation Rentals
-
Laie Vacation Rentals
-
Ko Olina Vacation Rentals
-
Haleiwa Vacation Rentals
-
Mākaha Vacation Rentals
-
Pāhoa Vacation Rentals
-
Lihue Vacation Rentals
-
Kapaa Vacation Rentals
-
Hanalei Vacation Rentals
-
Ocoee Vacation Rentals
-
Edgewater Vacation Rentals
-
Brookings Vacation Rentals
-
Mukilteo Vacation Rentals
-
Stanley Vacation Rentals
-
Harbor Springs Vacation Rentals
-
Sunset Beach Vacation Rentals
-
Atlantic Beach Vacation Rentals
-
Falmouth Vacation Rentals
-
Milledgeville Vacation Rentals
-
Okoboji Vacation Rentals
-
Edina Vacation Rentals
-
Lake George Cabin Rentals
-
Arlington Vacation Rentals
-
Vilano Beach Vacation Rentals
-
Yuma Vacation Rentals
-
Bandon Vacation Rentals
-
Waldorf Vacation Rentals
-
Sonora Vacation Rentals
-
Horseheads Vacation Rentals
-
Carefree Vacation Rentals
-
West Glacier Vacation Rentals
-
Ely Vacation Rentals