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

Vacation rentals in Wailea

Find 7,651 available house rentals from 29 partners
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Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $100 per night!

House Wailea
-60%
May 3 - May 10
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace, private pool & BBQ | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
$1,860$750
per night
Outstanding(168 ratings)
$1,860$750
per night
View deal
Condo Wailea
May 11 - May 18
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with barbecue, hot tub & patio | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$270
per night
Outstanding(109 ratings)
$270
per night
View deal
Condo Wailea
-44%
May 11 - May 18
Condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$495$276
per night
Outstanding(135 ratings)
$495$276
per night
View deal
Condo Wailea
-41%
May 11 - May 18
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
$340$202
per night
Outstanding(67 ratings)
$340$202
per night
View deal
House Wailea
-63%
May 14 - May 21
House ∙ 7 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$807$295
per night
(57 ratings)
$807$295
per night
View deal
Villa Wailea
Mar 13 - Mar 20
Villa ∙ 10 guests ∙ 4 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$1,382
per night
Outstanding(75 ratings)
$1,382
per night
View deal
House Wailea
May 5 - May 12
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with garden, terrace & jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
$675
per night
Outstanding(160 ratings)
$675
per night
View deal
Condo Wailea
-55%
May 3 - May 10
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with barbecue, hot tub & patio | Nature view

Wailea, Wailea-Makena, Hawaii, United States
$807$361
per night
Outstanding(2 ratings)
$807$361
per night
View deal
Condo Wailea
Apr 3 - Apr 10
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
Villa Wailea
-53%
Sep 14 - Sep 21
Villa ∙ 10 guests ∙ 4 bedrooms

Family-oriented villa with pool, grill & sauna | Next to the beach | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
$1,752$818
per night
Outstanding(162 ratings)
$1,752$818
per night
View deal
Condo Wailea
May 17 - May 24
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
Sep 20 - Sep 27
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$277
per night
Outstanding(72 ratings)
$277
per night
View deal
Condo Wailea
-56%
May 3 - May 10
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
$377$167
per night
Very good(1 rating)
$377$167
per night
View deal
Condo Wailea
-40%
May 25 - Jun 1
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
$672$400
per night
Outstanding(33 ratings)
$672$400
per night
View deal
Serviced apartment Wailea
-47%
May 3 - May 10
Serviced apartment ∙ 127 guests ∙ 3 bedrooms

Serviced apartment with garden, barbecue & pool

Wailea, Wailea-Makena, Hawaii, United States
$292$155
per night
Very good
$292$155
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
May 17 - May 24
-45%
$459
$252
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

5.0
Outstanding(12 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
May 21 - May 28
-57%
$483
$208
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly lovely condo with hot tub & pool

4.6
Excellent(25 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
May 14 - May 21
$479
per night
Condo ∙ 7 guests ∙ 4 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
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Vacation houses with Balconies or Patios

Condo  Wailea
May 3 - May 10
-62%
$365
$139
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
-53%
$425
$200
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
Sep 20 - Sep 27
$295
per night
Condo ∙ 8 guests ∙ 4 bedrooms

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

3.6
Good(66 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals with a balcony

House  Wailea
May 14 - May 21
$540
per night
House ∙ 6 guests ∙ 3 bedrooms

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

4.9
Outstanding(48 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
Oct 14 - Oct 21
$946
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Children-friendly charming condo with heated pool, barbecue & yard | Nature view | Close to the beach

4.9
Outstanding(45 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
Sep 20 - Sep 27
$256
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped charming condo with terrace, yard & pool | Nature view | Close to the beach

4.7
Excellent(117 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
See all offers

Best Vacation Home Deals in Wailea

Save up to 42%

House Wailea
Sep 14 - Sep 21
-18%
$241
$197
per night
House ∙ 6 guests ∙ 3 bedrooms

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

4.7
Excellent(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Apartment Wailea
Sep 22 - Sep 29
-33%
$402
$271
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Family-oriented rental apartment with barbeque, pool & garden | Close to the beach

5.0
Outstanding(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 17 - May 24
-42%
$494
$287
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, barbeque & pool

4.8
Outstanding(35 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

7,651 great rentals from 29 partner websites, such as Homelidays 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
Aug 13 - Aug 20
$251
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with patio, pool & barbecue

4.9
Outstanding(14 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
May 7 - May 14
$540
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented big house with grill, yard & terrace

5.0
Outstanding(111 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Aug 27 - Sep 3
-41%
$1,703
$999
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with garden, BBQ & hot tub

4.9
Outstanding(104 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
Dec 6 - Dec 13
-38%
$525
$325
per night
Condo ∙ 5 guests ∙ 5 bedrooms

Condo with terrace, heated pool & barbeque

5.0
Outstanding(143 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Sep 20 - Sep 27
$248
per night
Condo ∙ 6 guests ∙ 3 bedrooms

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

4.8
Outstanding(122 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Oct 14 - Oct 21
-28%
$625
$450
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with barbeque, pool & terrace

4.7
Excellent(104 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 $948
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 $338
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 $220
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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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 (6,350)
  • Air conditioning (6,717)
  • Kitchen (6,812)
  • Parking (280)
  • Balcony/patio (2,155)
  • WiFi (7,318)
  • Washing machine (5,827)
  • TV (6,794)
  • Microwave (5,698)
  • Dishwasher (4,353)
  • Grill (4,345)
  • No smoking (6,750)

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 (3/21 – 3/28). Prices reach an average of $633 per night. Prices decrease in a week of August (8/30 – 9/6), where average prices are $544.

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 April (4/11 – 4/18). Only 17% 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 7,651 rentals
💳 Possible discounts up to 67%
🌙 Nightly prices starting at $100
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,372 homes
312,971 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 312,971 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 $100 per night. $586 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $538 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,651 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 6,372 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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