KAYAK searches hundreds of travel sites at once for vacation home deals in Wailea
...and more
Here is why travelers choose KAYAK
Free to useThere are no hidden charges or fees.
Filter your dealsFilter by free cancellation, free breakfast and more.
Millions of reviewsCheck ratings based on millions of real guest reviews.
Booking Insights
KAYAK’s insights for vacation rentals in Wailea
Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Wailea with confidence.
Which month has the cheapest vacation rental rates in Wailea?
Vacation rentals are cheapest in Wailea in May, with average rates of $458. In comparison, November is the most expensive month, with prices at $1,307.
What is the cheapest day of the week to book a vacation rental in Wailea?
Tuesday offers the lowest rates in Wailea, with an average nightly price of $465. The highest prices are found on Sunday, with average rates at $1,373.
How early should you book a vacation rental in Wailea?
Book at least 4 days before your stay begins to get the best price for your Wailea vacation rental.
Cheapest month to stay with an average 37% drop in price.
Most expensive month to stay with an average 80% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.
KAYAK's top tips for finding Wailea vacation rental deals
For family-friendly Wailea vacation rentals, consider booking Ekahi 32A, a spectacular 2-bedroom condo with 2 bathrooms that can accommodate up to 7 people. Located in the peaceful Ekahi Village, this condo unit features spacious, air-conditioned rooms, an outdoor pool, laundry facilities, a well-fitted kitchen, and beach toys for kids. The property also has spacious lanais, where you can enjoy great views of the ocean and the surrounding gardens.
If you're looking for the best beachfront vacation rentals in Wailea, you can check into Wailea Beach Villa L409, a 4-bedroom villa with 3 bathrooms, that accommodates up to 9 people. The property features spacious rooms with flat-screen TVs, PlayStation, and iPod docks in bedrooms. It also includes a gourmet kitchen, a wine cooler, an outdoor grill, and a fitness center.
Those traveling with pets can check into The Villas at Fairmont Kea Lani. The vacation home welcomes pets of all sizes upon request at a fee. You can also check into Ekahi 13C, a 1-bedroom vacation rental that welcomes only one dog under 50 lbs at a fee. Cats aren’t allowed into the property. These vacation homes have a spacious playing area and a potty area for your pet.
Car owners or those visiting the destination with rented vehicles can find multiple hotels with free parking. For Wailea vacation rentals with free parking, consider booking Wailea Ekolu #607. The vacation home also features a private pool, an outdoor pool, and spacious rooms with a balcony. You can also book Maui Banyan, a 1-bedroom property with free parking, a private bathroom, and a well-fitted kitchen with an outdoor dining area.
For Wailea house rentals with a pool, consider booking Mana Kai 314C, a 2-bedroom apartment with a pool and fitness center. The property features spacious rooms with a private bathroom, a gourmet kitchen, laundry facilities, and free parking. You can also check into Makena Surf, which has an outdoor pool, a jacuzzi, and a private beach.
The best vacation rental properties in Wailea are Private Saltwater Spa and Outdoor Oasis - Luxurious Tropical Haven (10.0, 33 reviews), Villa Moana Maui (9.9, 20), and Remodeled,Ground Level, A/C Throughout,King Bed,Everything Needed for Kids/Beach (9.7, 49), based on ratings and reviews from real travelers.
If you’re looking for a cheap vacation rental in Wailea, you should consider visiting during the low season. The cheapest vacation homes in Wailea can be found in May and April.
The cheapest night for renting a vacation home in Wailea is Tuesday. In contrast, the most expensive is Sunday.
Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Wailea for 3 days.
The cheapest Wailea vacation rental found on KAYAK in the last 2 weeks was $278, while the most expensive was $402.
FAQs when booking a vacation home in Wailea
How much is a vacation rental for a week in Wailea?
The average price for a weekly Wailea vacation rental found by KAYAK users in the last 2 weeks is $3,973.
How much is a vacation rental for a month in Wailea?
The average price for a monthly Wailea vacation rental found by KAYAK users in the last 2 weeks is $17,027.
What types of vacation rentals are available in Wailea?
There are loads of different property types that you can make your vacation home in Wailea. You’ll find apartments, condos, cottages, houses, homestays, luxury tents and villas.
What are some of the most-loved vacation rentals available in Wailea?
What are the most popular Wailea vacation rentals for a large group?
If you’re a large group then you’ll need plenty of space. The highest rated vacation home that can sleep 6 people or more by KAYAK users is Wailea Elua Village.
How much is a vacation rental in Wailea for tonight?
In the last 72 hours, users have found Wailea vacation rentals for tonight for as low as $468. Search here for similar prices
How much is a vacation rental in Wailea for this weekend?
In the last 72 hours, users have found Wailea vacation rentals for this weekend for as low as $397 per night. Search here for similar prices
How can I find vacation rentals near me in Wailea?
Take a look at our vacation rentals map to find the best vacation rental homes near you.
What are the best vacation rentals for couples in Wailea?
For a quality romantic break with your partner, you can check into Grand Champions 2A Studio, a studio that can accommodate 2 people. The vacation home is air-conditioned, has a separate kitchen, and includes a hot tub. It also has an outdoor seating area where you can enjoy the best ocean views. Grand Champions 2A Studio is a short walk from Ulua and Mokapu beaches.
What vacation rentals in Wailea have barbecue facilities?
If you want to grill something while on vacation in Wailea, you can check into Maui Kamaole, which has a terrace with an outdoor grill. The vacation home also includes a heated pool and a kitchen with an outdoor dining area. You can also check into Kihei Akai, which has a patio with an outdoor grill. You can relax at the property’s outdoor furniture or enjoy ocean views from the balcony.
What vacation rentals in Wailea are close to Wailea Blue Golf Course?
For Wailea vacation rentals close to the golf course, you can check into Aston Maui Hill, which is just 2.5 miles away. The vacation home features spacious suites with furnished private balconies, 2 bathrooms, and a seating area. You can also check into Polo Beach Club Rentals, less than a mile from the golf course.
What vacation rentals in Wailea are close to Kahului Airport?
Castle Kamaole Sands offers an ideal option for visitors looking for vacation rentals close to Kahului Airport. The vacation home is just 15 miles from the airport and features an outdoor pool, a garden, a well-equipped kitchen, and a fitness center.
Where to stay in Wailea?
Our map will help you find the perfect place to stay in Wailea by showing you the exact location of each vacation rental.
Everything you need to know for your stay in Wailea
This site uses cookies and other tracking technologies for essential, functional, analytical, and advertising purposes. By using the site, you agree to our Terms & Conditions and our Privacy Policy.
For more information about how we process your information, please see our Privacy Policy.
We value your privacy
KAYAK and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyze navigation, to offer and measure personalized advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review your choices and withdraw your consent at any time by clicking the ’Privacy Preferences’ link in the page side navigation.
