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

Vacation rentals in Wailea

Find 7,744 available house rentals from 32 partners
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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $194 per night!

Condo Wailea
-35%
Sep 7 - Sep 14
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$425$277
per night
Outstanding(38 ratings)
$425$277
per night
View deal
Condo Wailea
Sep 7 - Sep 14
Condo ∙ 7 guests ∙ 4 bedrooms

Condo with patio, yard & BBQ | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$470
per night
Outstanding(104 ratings)
$470
per night
View deal
Condo Wailea
-35%
Apr 27 - May 4
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$588$379
per night
Outstanding(71 ratings)
$588$379
per night
View deal
Condo Wailea
May 10 - May 17
Condo ∙ 10 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$596
per night
Very good(66 ratings)
$596
per night
View deal
Condo Wailea
-43%
May 16 - May 23
Condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$310$176
per night
$310$176
per night
View deal
Condo Wailea
-64%
Aug 24 - Aug 31
Condo ∙ 8 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$1,153$410
per night
Outstanding(214 ratings)
$1,153$410
per night
View deal
Condo Wailea
-32%
May 7 - May 14
Condo ∙ 8 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$722$495
per night
Outstanding(98 ratings)
$722$495
per night
View deal
Condo Wailea
-32%
Aug 2 - Aug 9
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$585$400
per night
Excellent(23 ratings)
$585$400
per night
View deal
Condo Wailea
Sep 7 - Sep 14
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with patio, pool & barbecue

Wailea, Wailea-Makena, Hawaii, United States
$289
per night
Outstanding(12 ratings)
$289
per night
View deal
Condo Wailea
-45%
Sep 20 - Sep 27
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
$514$283
per night
Outstanding(3 ratings)
$514$283
per night
View deal
Condo Wailea
Apr 22 - Apr 29
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
$180
per night
Very good(1 rating)
$180
per night
View deal
Condo Wailea
Nov 22 - Nov 29
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with barbecue, hot tub & patio

Wailea, Wailea-Makena, Hawaii, United States
$599
per night
Outstanding(2 ratings)
$599
per night
View deal
Condo Wailea
May 20 - May 27
Condo ∙ 6 guests ∙ 6 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$262
per night
Outstanding(113 ratings)
$262
per night
View deal
Condo Wailea
-45%
Jun 15 - Jun 22
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with barbecue, heated pool & garden | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$422$232
per night
Outstanding(87 ratings)
$422$232
per night
View deal
Condo Wailea
Aug 15 - Aug 22
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with hot tub, garden & patio

Wailea, Wailea-Makena, Hawaii, United States
$850
per night
Outstanding(99 ratings)
$850
per night
View deal

Best vacation rentals with a balcony

Condo  Wailea
Apr 26 - May 3
-41%
$269
$203
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with pool, barbeque & patio

4.0
Very good(18 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
May 26 - Jun 2
$347
per night
Condo ∙ 4 guests ∙ 2 bedrooms

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

4.9
Outstanding(89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
May 26 - Jun 2
-58%
$520
$410
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with BBQ, pool & patio | Nature view

5.0
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
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Vacation rentals and apartments with air conditioning

Condo  Wailea
May 17 - May 24
$488
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with terrace, jacuzzi & yard | Mountain view

4.9
Outstanding(38 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
House  Wailea
Aug 23 - Aug 30
-24%
$358
$300
per night
House ∙ 6 guests ∙ 3 bedrooms

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

4.7
Excellent(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
Aug 31 - Sep 7
$583
per night
Condo ∙ 7 guests ∙ 4 bedrooms

Condo with patio, yard & BBQ | Nature view

4.9
Outstanding(105 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Apartments With Balconies or Patios

Condo  Wailea
Apr 19 - Apr 26
-50%
$505
$277
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ, pool & jacuzzi | Nature view

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Cottage  Wailea
Jun 7 - Jun 14
-58%
$566
$255
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
Jun 3 - Jun 10
-47%
$562
$335
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with jacuzzi, pool & barbecue | Nature view | Next to the beach

4.9
Outstanding(62 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Best Vacation Home Deals in Wailea

Save up to 90%

Condo Wailea
Apr 8 - Apr 15
-46%
$408
$216
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
Jun 14 - Jun 21
-90%
$448
$331
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully equipped condo with yard, heated pool & barbecue

4.9
Outstanding(123 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Jul 19 - Jul 26
-38%
$743
$457
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with terrace, barbeque & pool

5.0
Outstanding(6 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

7,744 great rentals from 32 partner websites, such as stayz or Casamundo, 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
Oct 18 - Oct 25
-28%
$769
$573
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with barbeque, pool & terrace

4.7
Excellent(106 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 31 - Jun 7
-51%
$600
$312
per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.8
Outstanding(67 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
May 26 - Jun 2
-25%
$358
$300
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped ample house with patio, pool & garden | Next to the beach

4.7
Excellent(68 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
Aug 15 - Aug 22
$575
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with pool, BBQ & terrace

4.9
Outstanding(91 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 23 - May 30
-66%
$909
$313
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped ample condo with BBQ, jacuzzi & pool | Nature view

4.9
Outstanding(85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 13 - May 20
$306
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool, hot tub & barbeque | Mountain view

5.0
Outstanding(61 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 $999
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 $426
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 $233
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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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 (6,302)
  • Air conditioning (6,804)
  • Kitchen (6,812)
  • Parking (312)
  • Balcony/patio (2,174)
  • WiFi (7,500)
  • Washing machine (5,488)
  • TV (6,872)
  • Microwave (5,763)
  • Dishwasher (4,376)
  • Grill (4,332)
  • No smoking (6,730)

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 $868 per night. Prices decrease in a week of May (5/24 – 5/31), where average prices are $477.

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 (2/14 – 2/21). Only 19% of the rentals are still available. On the contrary, only 43% of vacation rentals are unavailable in September (9/20 – 9/27).

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 7,712 rentals
💳 Possible discounts up to 90%
🌙 Nightly prices starting at $150
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,279 homes
326,496 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 326,496 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 $150 per night. $621 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $610 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,712 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 6,279 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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