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

Vacation rentals in Wailea

Find 7,644 available house rentals from 28 partners
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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $139 per night!

House Wailea
House ∙ 11 guests ∙ 5 bedrooms

Children-friendly wonderful house with private pool | City view

Wailea, Wailea-Makena, Hawaii, United States
from $833
per night
from $833
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with barbecue, hot tub & patio | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $492
per night
Outstanding(2 ratings)
from $492
per night
View deal
House Wailea
House ∙ 7 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $401
per night
(57 ratings)
from $401
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with jacuzzi, BBQ & garden

Wailea, Wailea-Makena, Hawaii, United States
from $2,058
per night
Excellent(49 ratings)
from $2,058
per night
View deal
Villa Wailea
Villa ∙ 10 guests ∙ 4 bedrooms

Fully equipped big villa with barbeque, pool & jacuzzi | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $1,095
per night
Outstanding(77 ratings)
from $1,095
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $350
per night
Outstanding(73 ratings)
from $350
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with hot tub, garden & patio

Wailea, Wailea-Makena, Hawaii, United States
from $1,053
per night
Outstanding(100 ratings)
from $1,053
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with garden, BBQ & terrace | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
from $1,392
per night
Outstanding(123 ratings)
from $1,392
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped pleasant condo with terrace, pool & jacuzzi | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $270
per night
Outstanding(40 ratings)
from $270
per night
View deal
House Wailea
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with garden, terrace & jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
from $1,014
per night
Outstanding(160 ratings)
from $1,014
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool, garden & barbeque | Water view | Perfect for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $249
per night
from $249
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $314
per night
Outstanding(67 ratings)
from $314
per night
View deal
House Wailea
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with garden, BBQ & hot tub

Wailea, Wailea-Makena, Hawaii, United States
from $1,090
per night
Outstanding(104 ratings)
from $1,090
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 6 bedrooms

Family-friendly nice condo with terrace, yard & jacuzzi | City view | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
from $320
per night
Outstanding(112 ratings)
from $320
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented condo with heated pool, garden & BBQ | Nature view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
from $324
per night
Outstanding(172 ratings)
from $324
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
from $207
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with garden, pool & jacuzzi | Nature view

3.8
Good(4 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Villa  Wailea
from $1,018
per night
Villa ∙ 7 guests ∙ 3 bedrooms

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

5.0
Outstanding(79 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $490
per night
Condo ∙ 8 guests ∙ 4 bedrooms

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

4.8
Outstanding(109 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Cottage  Wailea
from $279
per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage with garden, patio & BBQ

4.8
Outstanding(41 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
House  Wailea
from $571
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
Condo  Wailea
from $383
per night
Condo ∙ 8 guests ∙ 4 bedrooms

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

3.6
Good(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

Condo  Wailea
from $225
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ, pool & jacuzzi | Nature view

Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $270
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Nature view

4.9
Outstanding(82 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $234
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with BBQ, pool & jacuzzi

4.8
Outstanding(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Best Vacation Home Deals in Wailea

Save up to 8%

Condo Wailea
-8%
$303
from $278
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Children-friendly nice condo with garden, pool & patio | Close to the beach

4.5
Excellent(34 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

7,644 great rentals from 29 partner websites, such as Abritel or Booking.com, can be booked in Wailea. HomeToGo instantly shows the best offers by comparing all of the listed accommodations in Wailea from its various partners.

Budget-friendly Vacation Rentals in Wailea

Find Fantastic yet Inexpensive Offers

Condo Wailea
from $294
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

5.0
Outstanding(12 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $257
per night
House ∙ 8 guests ∙ 2 bedrooms

Family-oriented big house with pool, BBQ & jacuzzi | Beach view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $508
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped wonderful condo with jacuzzi, grill & pool | Next to the beach

4.9
Outstanding(96 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

Condo Wailea
from $342
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with barbecue, hot tub & patio | Nature view

4.8
Outstanding(108 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $470
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped ample condo with BBQ, jacuzzi & pool

4.9
Outstanding(90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $483
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with terrace, jacuzzi & yard | Mountain view

4.9
Outstanding(42 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 $938
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 $322
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 $222
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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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Wailea

  • Pool (6,366)
  • Air conditioning (6,708)
  • Kitchen (6,813)
  • Parking (261)
  • Balcony/patio (2,170)
  • WiFi (7,337)
  • Washing machine (5,807)
  • TV (6,818)
  • Microwave (5,754)
  • Dishwasher (4,401)
  • Grill (4,391)
  • No smoking (6,815)

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 February (2/21 – 2/28). Prices reach an average of $631 per night. Prices decrease in a week of September (9/20 – 9/27), where average prices are $536.

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 (5/2 – 5/9). Only 14% 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 7,644 rentals
💳 Possible discounts up to 66%
🌙 Nightly prices starting at $139
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,381 homes
317,017 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 317,017 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 $139 per night. $575 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $536 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,644 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 6,381 Condo and Apartment rental available for renting.

Are dogs allowed in vacation homes in Wailea?

If traveling with a dog in Wailea, 3% 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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