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Wailea holiday rentals

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Best Wailea vacation rentals

Most recommended vacation rentals in Wailea

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Wailea Grand Champions Villas - Coraltree Residence Collection - Wailea - Balcony
Wailea Grand Champions Villas - Coraltree Residence Collection
Wailea, Maui, HI, United States
8.7Very Good(185)
Parking
Free Wi-Fi
Pool
$656+
View availability
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations - Wailea - Patio
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations
Wailea, Maui, HI, United States
9.5Wonderful(4)
Free Wi-Fi
Pool
$567+
View availability
Wailea Elua Village - Coraltree Residence Collection - Wailea - Dining room
Wailea Elua Village - Coraltree Residence Collection
Wailea, Maui, HI, United States
8.8Very Good(158)
Parking
Free Wi-Fi
Pool
Spa
$1,207+
View availability
Kihei Akahi by Coldwell Banker Island Vacations - Wailea - Beach
Kihei Akahi by Coldwell Banker Island Vacations
Wailea, Maui, HI, United States
8.5Very Good(9)
Free Wi-Fi
Pool
$526+
View availability
Maui Kamaole by Coldwell Banker Island Vacations - Wailea - Living room
Maui Kamaole by Coldwell Banker Island Vacations
Wailea, Maui, HI, United States
8.2Very Good(5)
Free Wi-Fi
Pool
$569+
View availability
Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations - Wailea - Living room
Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations
Wailea, Maui, HI, United States
9.6Wonderful(11)
Free Wi-Fi
Pool
$796+
View availability
Kamaole Sands - Maui Condo & Home - Wailea - Beach
Kamaole Sands - Maui Condo & Home
Wailea, Maui, HI, United States
$652+
View availability
Ekahi Village - Wailea - Beach
Ekahi Village
Wailea, Maui, HI, United States
Free Wi-Fi
Pool
$784+
View availability
Wailea Sunset Condo - Ekolu #607 - Wailea - Balcony
Wailea Sunset Condo - Ekolu #607
Wailea, Maui, HI, United States
9.5Wonderful(33)
Parking
Free Wi-Fi
Pool
$734+
View availability
Maui Hill by Coldwell Banker Island Vacations - Wailea - Patio
Maui Hill by Coldwell Banker Island Vacations
Wailea, Maui, HI, United States
9.2Wonderful(25)
Free Wi-Fi
Pool
$769+
View availability
Maui Banyan - Wailea - Beach
Maui Banyan
Wailea, Maui, HI, United States
8.1Very Good(41)
Free Wi-Fi
Pool
$477+
View availability
Kihei Condo with Resort Amenities Walk to the Beach - Wailea - Living room
Kihei Condo with Resort Amenities Walk to the Beach
Wailea, Maui, HI, United States
7.7Good(37)
Free Wi-Fi
Pool
Spa
$475+
View availability
The Villas at Fairmont Kea Lani - Wailea
The Villas at Fairmont Kea Lani
Wailea, Maui, HI, United States
9.4Wonderful(5)
Free Wi-Fi
Pool
Pet-friendly
$6,412+
View availability
Mana Kai 311A - Wailea
Mana Kai 311A
Wailea, Maui, HI, United States
10Wonderful(1)
Free Wi-Fi
Pool
$846+
View availability
4-309 Kamaole SandsNewly Remodeled Steps to Kamaole 3 Beach! - Wailea
4-309 Kamaole SandsNewly Remodeled Steps to Kamaole 3 Beach!
Wailea, Maui, HI, United States
6.0Okay(7)
Parking
Free Wi-Fi
Pool
$703+
View availability
126 Hale Kamaole - Wailea
126 Hale Kamaole
Wailea, Maui, HI, United States
9.0Wonderful(14)
Parking
Free Wi-Fi
Pool
$612+
View availability
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KAYAK’s insights for holiday 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 October, with average rates of $915. In comparison, December is the most expensive month, with prices at $2,857.

What is the cheapest day of the week to book a vacation rental in Wailea?

Sunday offers the lowest rates in Wailea, with an average nightly price of $1,128. The highest prices are found on Friday, with average rates at $2,527.

How early should you book a vacation rental in Wailea?

Book at least 9 days before your stay begins to get the best price for your Wailea vacation rental.
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Good to know

Low season

April

High season

April
Cheapest month to stay with an average 0% drop in price.
Most expensive month to stay with an average 0% rise in price.

KAYAK's top tips for finding Wailea holiday 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.
  • Beachfront is the most popular holiday rental property amenity in Wailea
  • Holiday rentals in Wailea are around 64% more expensive than hotels on average. Search here to compare prices for all accommodation types in Wailea.
  • The best holiday rental properties in Wailea are Luxe Ocean View Hideaway On Wailea Old Blue Golf Course (9.9, 53 reviews), Romantic 1 BR Condo with King Tempurpedic (9.8, 20), and Wailea Ekahi 21F (9.6, 54), based on ratings and reviews from real travellers.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Wailea for 6 days.
See more tips

FAQs when booking a holiday home in Wailea

  • What types of holiday rentals are available in Wailea?

    There are loads of different property types that you can make your holiday home in Wailea. You’ll find apartments, condos, cottages, houses, luxury tents and villas.

  • What are some of the most-loved holiday rentals available in Wailea?

    There are many types of properties available for Wailea holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Maui Banyan Vacation Club and Wailea Grand Champions Villas - Coraltree Residence Collection.

  • Are there any pet-friendly holiday rentals in Wailea?

    There are a number of dog and pet-friendly Wailea holiday rentals, with around 4% allowing you to bring your pet along with you.

  • How much is a holiday rental in Wailea for tonight?

    In the last 72 hours, users have found Wailea holiday rentals for tonight for as low as $1,045. Search here for similar prices

  • How can I find holiday rentals near me in Wailea?

    Take a look at our holiday rentals map to find the best holiday 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.

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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 holiday rental.

Everything you need to know for your stay in Wailea

Wailea holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Wailea. Find cheap holiday homes to rent in Wailea. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Wailea that suits you best.

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