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

Vacation rentals in Wailea

Find 7,647 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 $196 per night!

Condo Wailea
-32%
Jun 25 - Jul 2
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool, BBQ & patio | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
$377$272
per night
Outstanding(57 ratings)
$377$272
per night
View deal
Condo Wailea
-25%
Dec 8 - Dec 15
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with BBQ & pool

Wailea, Wailea-Makena, Hawaii, United States
$537$394
per night
Outstanding(60 ratings)
$537$394
per night
View deal
Condo Wailea
-26%
Apr 21 - Apr 28
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$488$375
per night
Outstanding(68 ratings)
$488$375
per night
View deal
Condo Wailea
Jun 2 - Jun 9
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly nice condo with BBQ, heated pool & yard | Mountain view | Close to the beach | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
$568
per night
Outstanding(24 ratings)
$568
per night
View deal
Condo Wailea
-35%
Oct 11 - Oct 18
Condo ∙ 4 guests ∙ 1 bedroom

Condo with barbeque, garden & pool

Wailea, Wailea-Makena, Hawaii, United States
$331$222
per night
Outstanding(23 ratings)
$331$222
per night
View deal
Condo Wailea
-32%
Apr 29 - May 6
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped spacious condo with BBQ, patio & pool | Nature view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
$702$496
per night
Excellent(24 ratings)
$702$496
per night
View deal
Condo Wailea
-25%
May 8 - May 15
Condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$254$196
per night
Outstanding(54 ratings)
$254$196
per night
View deal
Condo Wailea
-38%
Apr 23 - Apr 30
Condo ∙ 4 guests ∙ 2 bedrooms

Fully equipped condo with barbecue, patio & garden | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$537$350
per night
Very good(49 ratings)
$537$350
per night
View deal
Condo Wailea
Jul 17 - Jul 24
Condo ∙ 5 guests ∙ 1 bedroom

Condo with patio, private pool & barbecue

Wailea, Wailea-Makena, Hawaii, United States
$179
per night
Outstanding(114 ratings)
$179
per night
View deal
Condo Wailea
-37%
May 18 - May 25
Condo ∙ 4 guests ∙ 2 bedrooms

Children-friendly charming condo with pool, terrace & yard | Next to the beach | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
$595$426
per night
Outstanding(135 ratings)
$595$426
per night
View deal
Condo Wailea
-66%
Apr 8 - Apr 15
Condo ∙ 4 guests ∙ 3 bedrooms

Fully equipped wonderful condo with grill, patio & yard | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
$611$241
per night
Excellent(55 ratings)
$611$241
per night
View deal
House Wailea
Aug 16 - Aug 23
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped House with Yard, Grill & Patio | Nature View | Next to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$480
per night
Excellent(63 ratings)
$480
per night
View deal
House Wailea
Feb 25 - Mar 4
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with grill, yard & terrace | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$527
per night
Excellent(94 ratings)
$527
per night
View deal
Condo Wailea
May 7 - May 14
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with yard, heated pool & patio | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
$485
per night
Outstanding(53 ratings)
$485
per night
View deal
Condo Wailea
Jul 6 - Jul 13
Condo ∙ 8 guests ∙ 4 bedrooms

Children-friendly condo with BBQ & pool | Next to the beach | Dogs allowed

Wailea, Wailea-Makena, Hawaii, United States
$372
per night
(2 ratings)
$372
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
Apr 7 - Apr 14
-49%
$421
$219
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with patio, barbeque & pool

4.2
Very good(27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
Apr 21 - Apr 28
-65%
$1,076
$348
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice condo with barbecue & pool | Next to the beach

4.7
Excellent(35 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
Aug 22 - Aug 29
$568
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly nice condo with BBQ, heated pool & yard | Mountain view | Close to the beach | Suitable for remote work

5.0
Outstanding(24 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Apartments With Balconies or Patios

Cottage  Wailea
May 1 - May 8
-55%
$561
$275
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
Jul 5 - Jul 12
$274
per night
Condo ∙ 2 guests ∙ 1 bedroom

Fully equipped charming condo with garden, terrace & heated pool | Nature view | Beach nearby

4.9
Outstanding(85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
May 18 - May 25
$367
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
See all offers

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%
$1,359
$649
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%
$300
$248
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

Best Vacation Home Deals in Wailea

Save up to 46%

Condo Wailea
Apr 8 - Apr 15
-46%
$421
$219
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
May 13 - May 20
-44%
$529
$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 23 - Apr 30
-36%
$534
$344
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

7,647 great rentals from 28 partner websites, such as Vrbo 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
$318
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
$379
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
Jul 19 - Jul 26
$244
per night
Condo ∙ 4 guests ∙ 2 bedrooms

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

4.9
Outstanding(204 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
Apr 10 - Apr 17
$621
per night
House ∙ 6 guests ∙ 3 bedrooms

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

4.9
Outstanding(46 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Aug 30 - Sep 6
-24%
$379
$288
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

5.0
Outstanding(3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Dec 3 - Dec 10
-28%
$625
$450
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with pool, garden & patio

4.8
Outstanding(123 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 $960
per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $960
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 $470
per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $470
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 $256
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $256
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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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 (6,112)
  • Air conditioning (6,606)
  • Kitchen (6,596)
  • Parking (301)
  • Balcony/patio (2,156)
  • WiFi (7,282)
  • Washing machine (5,286)
  • TV (6,646)
  • Microwave (5,686)
  • Dishwasher (4,313)
  • Grill (4,253)
  • No smoking (6,639)

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 (12/20 – 12/27). Prices reach an average of $812 per night. Prices decrease in a week of September (9/6 – 9/13), where average prices are $490.

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 February (2/15 – 2/22). Only 11% of the rentals are still available. On the contrary, only 39% of vacation rentals are unavailable in July (7/19 – 7/26).

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 7,647 rentals
💳 Possible discounts up to 58%
🌙 Nightly prices starting at $196
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,237 homes
323,158 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 323,158 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 $196 per night. $620 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $608 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,647 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 6,237 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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