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

Vacation rentals in Wailea

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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $152 per night!

Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, hot tub & patio | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $415
per night
Outstanding(107 ratings)
from $415
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with patio, pool & barbecue

Wailea, Wailea-Makena, Hawaii, United States
from $351
per night
Outstanding(10 ratings)
from $351
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with garden, terrace & heated pool | Perfect for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $556
per night
Outstanding(39 ratings)
from $556
per night
View deal
Condo Wailea
Condo ∙ 10 guests ∙ 3 bedrooms

Condo with hot tub, pool & barbecue | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $928
per night
Outstanding(61 ratings)
from $928
per night
View deal
House Wailea
House ∙ 10 guests ∙ 4 bedrooms

Child-friendly spacious house with terrace, private pool & hot tub | Nature view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $1,150
per night
Outstanding(96 ratings)
from $1,150
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
from $515
per night
Outstanding(113 ratings)
from $515
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Condo with barbecue, heated pool & garden | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
from $248
per night
Outstanding(91 ratings)
from $248
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with BBQ & pool | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $350
per night
Outstanding(74 ratings)
from $350
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Condo with patio, barbeque & pool

Wailea, Wailea-Makena, Hawaii, United States
$203 from $186
per night
Very good(27 ratings)
$203 from $186
per night
View deal
Villa Wailea
Villa ∙ 10 guests ∙ 3 bedrooms

Family-oriented villa with pool, grill & sauna | Next to the beach | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $1,054
per night
Outstanding(166 ratings)
from $1,054
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 2 bedrooms

Fully equipped nice condo with grill & pool | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $280
per night
Outstanding(55 ratings)
from $280
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool, garden & barbecue | Nature view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $267
per night
Outstanding(71 ratings)
from $267
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped beautiful condo with hot tub, pool & BBQ | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $317
per night
Outstanding(67 ratings)
from $317
per night
View deal
House Wailea
House ∙ 7 guests ∙ 2 bedrooms

Vacation home with patio, heated pool & BBQ | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $392
per night
(57 ratings)
from $392
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, yard & patio | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $293
per night
Outstanding(237 ratings)
from $293
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
from $219
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with barbecue, patio & pool

3.5
Good(34 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $532
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly wonderful condo with patio, hot tub & BBQ | City view | Beach nearby

4.9
Outstanding(30 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $380
per night
Condo ∙ 8 guests ∙ 3 bedrooms

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

3.6
Good(67 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
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Vacation houses with Balconies or Patios

Cabin  Wailea
from $285
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with garden, patio & BBQ

4.8
Outstanding(41 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $396
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool, patio & yard | Nature view

4.9
Outstanding(165 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
House  Wailea
from $484
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with yard, patio & grill | Nature view | Next to the beach

4.7
Excellent(63 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

House  Wailea
from $775
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home with yard, BBQ & terrace | Mountain view | Perfect for remote work

4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $377
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, pool & patio

5.0
Outstanding(104 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $281
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Nature view

4.9
Outstanding(84 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Budget-friendly Vacation Rentals in Wailea

Find Fantastic yet Inexpensive Offers

Condo Wailea
from $357
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with hot tub, heated pool & BBQ | City view

5.0
Outstanding(73 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $470
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with hot tub, barbeque & pool

4.8
Outstanding(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $779
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Fully equipped condo with garden, barbecue & pool | Beach nearby

4.6
Excellent(34 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Top-Rated Rentals and Accommodations in Wailea

Book Vacation Rental Offers with the Highest User Rating

House Wailea
from $734
per night
House ∙ 7 guests ∙ 3 bedrooms

House with terrace, garden & private pool | Suitable for remote work

4.9
Outstanding(93 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
from $1,008
per night
Villa ∙ 7 guests ∙ 2 bedrooms

Fully equipped nice villa with hot tub, terrace & barbeque | Nature view | Beach nearby | Good for workation

5.0
Outstanding(75 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $472
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Children-friendly spacious condo with pool, barbeque & jacuzzi | Nature view | Close to the beach

4.9
Outstanding(74 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Customer ratings and reviews

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 $1,102
per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 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 $416
per night
HomeToGo
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 $209
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

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Popular Rental Amenities in Wailea

  • Pool (6,040)
  • Air conditioning (6,437)
  • Kitchen (6,496)
  • Parking (295)
  • Balcony/patio (2,205)
  • WiFi (6,954)
  • Washing machine (6,049)
  • TV (6,555)
  • Microwave (5,647)
  • Dishwasher (4,313)
  • Grill (4,235)
  • No smoking (6,534)

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, nearly half 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 March (3/21 – 3/28). Prices reach an average of $637 per night. Prices decrease in a week of September (9/13 – 9/20), where average prices are $552.

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 May (5/23 – 5/30). Only 2% of the rentals are still available. On the contrary, only 43% of vacation rentals are unavailable in September (9/13 – 9/20).

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 7,270 rentals
💳 Possible discounts up to 11%
🌙 Nightly prices starting at $152
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 5,956 homes
12 reviews
Wailea vacation rentals have an average rating of 4.3/5 on 12 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in Wailea is priced at $152 per night. $581 is the average nightly price for condos in Wailea. House rentals in Wailea cost $808 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,270 rentals available for booking for your upcoming vacation.

What are the most popular amenities for vacation rentals in Wailea?

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

How many vacation homes with a pool are in Wailea?

Wailea has 5,956 Condo and Apartment rental available for renting.

Are dogs allowed in vacation homes in Wailea?

If traveling with a dog in Wailea, 4% of vacation rentals allow pets.

What are the best months to travel to Wailea?

If you are choosing a vacation rental in Wailea, keep in mind that rainy season is typically in March or November, with January often being the driest.

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