Vacation rentals in Wailea - HomeToGo base64Hash Vacation rentals in Wailea - HomeToGo

Vacation rentals in Wailea

Browse 6,597 available vacation homes and compared across 28 trusted partners
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Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 6,597 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool & grill | Sea view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers ocean views, beach access, a pool, and a kitchen, accommodating up to six guests for a perfect getaway.
from $507
per night
Outstanding(128 ratings)
from $507
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with jacuzzi, heated pool & patio | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a heated pool, hot tub, kitchen, and mountain views, perfect for families of up to 8.
from $533
per night
Outstanding(34 ratings)
from $533
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Children-friendly wonderful condo with pool & BBQ | Water view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers beach access, a pool, a kitchen, and a balcony with a sea view, perfect for family gatherings.
from $333
per night
Outstanding(115 ratings)
from $333
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, beach access, and a balcony with sea views, perfect for family getaways and events.
from $337
per night
Outstanding(13 ratings)
from $337
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, heated pool & yard | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a heated pool, hot tub, and balcony, perfect for a group of six seeking relaxation and fun.
from $315
per night
Excellent(45 ratings)
from $315
per night
View deal
Condo Wailea
Condo ∙ 5 guests ∙ 1 bedroom

Child-friendly condo with pool, BBQ & terrace | Nature view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a pool, spa, kitchen, yard, balcony, and parking, perfect for a memorable family getaway.
from $209
per night
Very good(54 ratings)
from $209
per night
View deal
Condo Wailea
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with jacuzzi, pool & BBQ

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, hot tub, and balcony, accommodating up to 7 for a perfect vacation retreat.
from $319
per night
Outstanding(1 rating)
from $319
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with patio, yard & private pool | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo features a private pool, hot tub, sauna, and a spacious yard, perfect for a vacation with family or friends.
from $419
per night
Outstanding(85 ratings)
from $419
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 3 bedrooms

Family-friendly wonderful condo with yard, jacuzzi & patio | City view | Next to the beach | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This waterfront condo in Wailea offers beach access, a heated pool, hot tub, and a family-friendly yard for unforgettable vacations.
from $218
per night
Outstanding(13 ratings)
from $218
per night
View deal
House Wailea
House ∙ 5 guests ∙ 2 bedrooms

Children-friendly charming vacation home with barbeque & yard | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a kitchen, yard, balcony, and parking, perfect for families seeking a memorable getaway.
from $641
per night
Outstanding(36 ratings)
from $641
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly condo with heated pool, terrace & barbeque | Nature view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a heated pool, kitchen, and balcony, perfect for families seeking a memorable getaway.
from $348
per night
from $348
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped condo with pool, hot tub & terrace | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, hot tub, balcony, and kitchen, accommodating up to 8 guests for an unforgettable getaway.
from $589
per night
Outstanding(122 ratings)
from $589
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Child-friendly wonderful condo with terrace, hot tub & heated pool | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $279
per night
Outstanding(2 ratings)
from $279
per night
View deal
Apartment Wailea
Apartment ∙ 4 guests ∙ 1 bedroom

Children-friendly holiday apartment with pool | Water view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This Wailea apartment features ocean views, beach access, a pool, and a kitchen, perfect for a family getaway.
from $195
per night
Excellent(48 ratings)
from $195
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with pool, patio & BBQ

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, balcony, and parking, accommodating up to 8 guests for an unforgettable getaway.
from $431
per night
Very good(26 ratings)
from $431
per night
View deal

Vacation rentals with a balcony

Condo  Wailea
from $586
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly condo with grill, pool & yard | City view | Close to the beach

5.0
Outstanding(10 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $224
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ, pool & jacuzzi | Nature view

4.8
Outstanding(41 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $276
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with hot tub, yard & pool

4.9
Outstanding(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Vacation houses with Balconies or Patios

Apartment  Wailea
from $220
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Family-oriented lovely rental apartment with barbecue, hot tub & pool | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $385
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Family-oriented condo with grill, terrace & garden | Close to the beach

3.6
Good(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $267
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Mountain view

4.9
Outstanding(90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

Condo  Wailea
from $290
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with yard, hot tub & heated pool | Mountain view

4.9
Outstanding(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $178
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with yard, BBQ & pool

5.0
Outstanding(4 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Apartment  Wailea
from $218
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday apartment with pool, BBQ & hot tub | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Wailea offering exceptional value for money

House Wailea
from $1,071
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, hot tub & BBQ | Nature view

4.9
Outstanding(107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $455
per night
Condo ∙ 8 guests ∙ 2 bedrooms

Condo with barbecue, hot tub & heated pool

4.9
Outstanding(8 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $2,768
per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with grill, private pool & yard | Mountain view

5.0
Outstanding(125 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Top-Rated Vacation rentals in Wailea

Book the highest-rated Wailea vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Wailea
from $583
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly condo with hot tub & heated pool

4.9
Outstanding(87 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $887
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, garden & patio

4.9
Outstanding(102 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $448
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, patio & grill

5.0
Outstanding(89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Wailea

How are reviews collected?
Robert M.
Guest verified by HomeToGo

Great place, everything you need and want for you stay. Living area and Master bedroom views great.

Reviewed on 9/25/2024 | Group
Condo Wailea
from $1,327
per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Kerry H.
Guest verified by HomeToGo

We loved this condo for our family of four (2 teenage boys). It had enough space for us to spread out. The location is perfect! Easy access to the beach, town and the most amazing spot to watch the sunset! Someone in the reviews mentioned road noise, I live in a rural quiet place and was a bit worried, but it was not an issue at all!

Reviewed on 10/30/2023 | Family
Condo Wailea
from $421
per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
David M.
Guest verified by HomeToGo

A great clean affordable option for a week away. Many options within walking distance and everything you need to enjoy your stay is supplied.

Reviewed on 10/27/2023 | Couple
Condo Wailea
from $267
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Wailea

  • Pool (5,650)
  • Air conditioning (5,739)
  • Kitchen (5,841)
  • Parking (273)
  • Balcony/patio (2,565)
  • WiFi (5,896)
  • Washing machine (5,050)
  • TV (5,857)
  • Microwave (4,979)
  • Dishwasher (4,512)
  • Grill (4,416)
  • No smoking (5,652)

Finding a rental with a pool is easy in Wailea. Most of the rentals include pools. In addition, more Condo have pools than any other property type. They are an excellent choice if you go in a group of 5, as that is the number of people they can accommodate on average. If you would also like to be close to the water, one-third of the properties with a pool are within 2 miles of the waterfront.

Price and Availability Index in Wailea

Click on any bar to see price and availability information

Vacation Rental Price Information in Wailea

We analyzed price data and input them into this graph, which shows vacation rental prices for the next year in Wailea. The most expensive prices are in December (12/26 – 1/2). Prices reach an average of $925 per night. Prices decrease in a week of May (5/2 – 5/9), where average prices are $774.

Rental availability information in Wailea

The availability graph shows the busiest months to book a vacation rental in Wailea. The week with the highest booking rate is in January (1/30 – 2/6). Only 33% of the rentals are still available. On the contrary, only 22% of vacation rentals are unavailable in July (7/18 – 7/25).

Experience the magic of Maui from your Wailea vacation home

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

What are the best activities for families in Wailea?

Ocean adventures for the whole family

Learn more about Hawaiian sea life with your family at the Maui Ocean Center, the top-rated aquarium of Hawaii. You don't need to get in the water to see live coral, sharks, turtles, and countless colorful fish. Aside from their many exhibits, they also offer educational tours and interactive presentations for a guided encounter with Hawaii's marine life.

For an even deeper ocean experience, travel a hundred feet below the surface with Atlantis Submarines. Their comfortable passenger vessels will carry your family under the sea in style, letting you observe sea life that's rarely seen by humans.

Where are the unique attractions in Wailea?

Maui's best beaches

Wailea Beach is consistently rated as one of the best beaches in the world. A wide, crescent-shaped beach with golden sand, Wailea beach also has calm waters—making it perfect for snorkeling, paddle boarding, and swimming.

Set on Maui's southwestern shores, Makena Beach State Park offers a secluded alternative to some of the more crowded beaches. Also known as Big Beach, Makena Beach is dramatically set between two black lava outcroppings.

Information about vacation rentals in Wailea

🏡 Vacation rentals available 6,597 rentals
🌙 Nightly prices starting at $151
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 5,764 homes
26 reviews
Wailea vacation rentals have an average rating of 4.4/5 on 26 reviews left by travelers.

Frequently Asked Questions

What is the price per night for a vacation rental in Wailea?

Prices for vacation rentals in Wailea start from $151 per night. Nightly prices for condos are $661 on average. Apartment rentals in Wailea cost on average $563 per night.

How many vacation homes are available to book in Wailea?

There are 6,597 vacation rentals in Wailea to browse and rent for your next trip.

What amenities are most popular for vacation rentals in Wailea?

Travelers search for Pool, Air conditioning, and Kitchen when booking a vacation rental in Wailea.

How many vacation rentals with a pool are in Wailea?

There are 5,764 vacation homes across 28 providers in Wailea.

Are dogs allowed in vacation homes in Wailea?

Absolutely, there are 163 vacation rentals in Wailea that allow dogs , with an average price of $2,089 per night.

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