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 $186 per night!

Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Family-friendly condo with terrace, pool & hot tub | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $287
per night
Excellent(122 ratings)
from $287
per night
View deal
Villa Wailea
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with garden, patio & grill

Wailea, Wailea-Makena, Hawaii, United States
from $1,123
per night
Outstanding(108 ratings)
from $1,123
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 $281
per night
Outstanding(55 ratings)
from $281
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 $974
per night
Outstanding(166 ratings)
from $974
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $318
per night
Outstanding(67 ratings)
from $318
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 $516
per night
Outstanding(113 ratings)
from $516
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 $353
per night
Outstanding(74 ratings)
from $353
per night
View deal
House Wailea
House ∙ 7 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $736
per night
Outstanding(93 ratings)
from $736
per night
View deal
House Wailea
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped ample house with patio & pool | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $257
per night
Excellent(68 ratings)
from $257
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Family-friendly wonderful condo with heated pool & jacuzzi | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $275
per night
Outstanding(54 ratings)
from $275
per night
View deal
House Wailea
House ∙ 7 guests ∙ 2 bedrooms

Vacation home with patio, heated pool & BBQ

Wailea, Wailea-Makena, Hawaii, United States
from $393
per night
(57 ratings)
from $393
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $385
per night
Good(67 ratings)
from $385
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $294
per night
Outstanding(237 ratings)
from $294
per night
View deal
Villa Wailea
Villa ∙ 7 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $982
per night
Outstanding(75 ratings)
from $982
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $280
per night
Outstanding(71 ratings)
from $280
per night
View deal

Vacation rentals and apartments with air conditioning

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
Air conditioning
View deal
Condo  Wailea
from $491
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped ample condo with BBQ, jacuzzi & pool

4.9
Outstanding(91 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $413
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, hot tub & patio

4.8
Outstanding(107 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
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Vacation houses with Balconies or Patios

Cabin  Wailea
from $286
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with garden, patio & BBQ

4.8
Outstanding(42 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $338
per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

5.0
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $392
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
See all offers

Vacation rentals with a balcony

Condo  Wailea
from $383
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, pool & patio | Nature view

5.0
Outstanding(104 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $258
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with yard, private pool & grill

5.0
Outstanding(72 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
House  Wailea
from $778
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
See all offers

Budget-friendly Vacation Rentals in Wailea

Find Fantastic yet Inexpensive Offers

Villa Wailea
from $1,130
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Family-oriented villa with pool, grill & patio | Nature view | Close to the beach

5.0
Outstanding(65 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $348
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with patio, pool & barbecue

4.8
Outstanding(10 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $247
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with barbecue, heated pool & garden | Mountain view

4.9
Outstanding(91 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 $295
per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

4.9
Outstanding(39 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $923
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, hot tub & BBQ

4.9
Outstanding(98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $518
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

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 $1,117
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 $208
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 (6,052)
  • Air conditioning (6,428)
  • Kitchen (6,489)
  • Parking (296)
  • Balcony/patio (2,205)
  • WiFi (6,941)
  • Washing machine (6,007)
  • TV (6,564)
  • Microwave (5,657)
  • Dishwasher (4,328)
  • Grill (4,241)
  • No smoking (6,544)

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 (3/14 – 3/21). Prices reach an average of $614 per night. Prices decrease in a week of August (8/23 – 8/30), where average prices are $523.

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 (5/30 – 6/6). Only 10% of the rentals are still available. On the contrary, only 43% of vacation rentals are unavailable in August (8/30 – 9/6).

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 7,303 rentals
🌙 Nightly prices starting at $186
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,021 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 $186 per night. $584 is the average nightly price for condos in Wailea. House rentals in Wailea cost $829 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,303 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 6,021 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.

Find the perfect accommodation to stay in Wailea

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