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

Vacation rentals in Wailea

Find 7,659 available house rentals from 28 partners
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1 guest
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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $185 per night!

Condo Wailea
Jan 13 - Jan 20
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with pool, terrace & barbeque | City view

Wailea, Wailea-Makena, Hawaii, United States
$595
per night
Excellent(21 ratings)
$595
per night
View deal
Serviced apartment Wailea
May 3 - May 10
Free cancellation
Serviced apartment ∙ 127 guests ∙ 3 bedrooms

Serviced apartment with garden, barbecue & pool

Wailea, Wailea-Makena, Hawaii, United States
$240
per night
Very good
$240
per night
View deal
Condo Wailea
-17%
Jun 14 - Jun 21
Condo ∙ 4 guests ∙ 2 bedrooms

Family-friendly charming condo with jacuzzi, pool & yard | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
$211$244
per night
Outstanding(206 ratings)
$211$244
per night
View deal
House Wailea
May 17 - May 24
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with garden, terrace & jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
$1,034
per night
Outstanding(155 ratings)
$1,034
per night
View deal
Condo Wailea
-24%
Apr 22 - Apr 29
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$452$357
per night
Outstanding(69 ratings)
$452$357
per night
View deal
Condo Wailea
-45%
Sep 3 - Sep 10
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
$454$298
per night
$454$298
per night
View deal
Condo Wailea
-25%
May 17 - May 24
Condo ∙ 4 guests ∙ 2 bedrooms

Child-friendly wonderful condo with grill, pool & terrace | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
$256$196
per night
Outstanding(54 ratings)
$256$196
per night
View deal
Villa Wailea
Feb 11 - Feb 18
Villa ∙ 10 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$1,663
per night
Outstanding(70 ratings)
$1,663
per night
View deal
Condo Wailea
May 10 - May 17
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$312
per night
Outstanding(171 ratings)
$312
per night
View deal
Condo Wailea
-71%
Sep 9 - Sep 16
Condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly nice condo with terrace, barbecue & pool | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$1,548$509
per night
Outstanding(212 ratings)
$1,548$509
per night
View deal
Condo Wailea
May 22 - May 29
Condo ∙ 6 guests ∙ 6 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$329
per night
Outstanding(111 ratings)
$329
per night
View deal
House Wailea
May 13 - May 20
House ∙ 7 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$732
per night
Outstanding(90 ratings)
$732
per night
View deal
Condo Wailea
Oct 25 - Nov 1
Condo ∙ 4 guests ∙ 2 bedrooms

Child-friendly condo with grill, pool & jacuzzi | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$233
per night
Outstanding(164 ratings)
$233
per night
View deal
Condo Wailea
May 13 - May 20
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with heated pool, jacuzzi & patio | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
$487
per night
Outstanding(53 ratings)
$487
per night
View deal
Condo Wailea
-31%
Sep 23 - Sep 30
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$373$270
per night
Outstanding(63 ratings)
$373$270
per night
View deal

Best vacation rentals with a balcony

Resort  Wailea
Jul 19 - Jul 26
$185
per night
Resort ∙ 4 guests ∙ 1 bedroom

Fully equipped beautiful resort with patio & pool | Beach nearby

3.5
Good(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
May 7 - May 14
-57%
$1,632
$674
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with heated pool & barbecue | Garden view

Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
Balcony
View deal
Condo  Wailea
Mar 23 - Mar 30
-35%
$273
$195
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with Pool, Terrace & Barbecue

4.0
Very good(18 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Apartments With Balconies or Patios

Cottage  Wailea
May 1 - May 8
-55%
$566
$269
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
Condo  Wailea
May 18 - May 25
$397
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with BBQ, pool & patio | Nature view

5.0
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
May 28 - Jun 4
$350
per night
Condo ∙ 4 guests ∙ 1 bedroom

Fully equipped beautiful condo with BBQ, yard & pool | Beach nearby

5.0
Outstanding(51 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Best Vacation Home Deals in Wailea

Save up to 46%

Condo Wailea
May 13 - May 20
-44%
$533
$326
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with barbeque, heated pool & terrace | Nature view

5.0
Outstanding(56 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 8 - Apr 15
-46%
$408
$214
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with patio, barbeque & pool

4.2
Very good(27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 23 - Apr 30
-36%
$575
$331
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-oriented nice condo with BBQ & heated pool | Nature view | Close to the beach

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

7,659 great rentals from 28 partner websites, such as FeWo-direkt or Vio.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
Apr 3 - Apr 10
$323
per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.8
Outstanding(67 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Jun 12 - Jun 19
$401
per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.9
Outstanding(36 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 1 - Apr 8
$236
per night
Condo ∙ 3 guests ∙ 2 bedrooms

Fully Equipped Condo with Yard, Barbeque & Patio | Mountain View | Close to the Beach | Suitable for Remote Work

5.0
Outstanding(74 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
Apr 29 - May 6
-29%
$709
$487
per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.9
Outstanding(71 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
May 14 - May 21
-21%
$813
$595
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden & barbeque

5.0
Outstanding(58 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Aug 30 - Sep 6
-24%
$647
$364
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

5.0
Outstanding(3 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 $953
per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $953
per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
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 $450
per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $450
per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
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 $247
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $247
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
HomeToGo
View deal

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Trust in the quality and comfort of your stay with verified guest reviews.

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Spend your budget exactly as planned by comparing thousands of providers.

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Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

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

Popular Rental Amenities in Wailea

  • Pool (6,262)
  • Air conditioning (6,730)
  • Kitchen (6,742)
  • Parking (297)
  • Balcony/patio (2,164)
  • WiFi (7,412)
  • Washing machine (5,424)
  • TV (6,793)
  • Microwave (5,739)
  • Dishwasher (4,359)
  • Grill (4,299)
  • No smoking (6,686)

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 December (12/13 – 12/20). Prices reach an average of $762 per night. Prices decrease in a week of May (5/10 – 5/17), where average prices are $485.

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 December (12/13 – 12/20). Only 18% of the rentals are still available. On the contrary, only 40% of vacation rentals are unavailable in July (7/12 – 7/19).

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 7,659 rentals
💳 Possible discounts up to 90%
🌙 Nightly prices starting at $185
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,253 homes
324,656 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 324,656 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 $185 per night. $614 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $596 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,659 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 6,253 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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