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

Vacation rentals in Wailea

Find 7,518 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 $187 per night!

House Wailea
-49%
Jun 3 - Jun 10
House ∙ 7 guests ∙ 4 bedrooms

House with Patio, Heated Pool & BBQ | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$890$437
per night
(57 ratings)
$890$437
per night
View deal
Condo Wailea
-25%
May 24 - May 31
Condo ∙ 4 guests ∙ 2 bedrooms

Child-Friendly Beautiful Condo with Terrace, Pool & Barbeque | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$254$196
per night
Outstanding(54 ratings)
$254$196
per night
View deal
Condo Wailea
-24%
Jun 7 - Jun 14
Condo ∙ 4 guests ∙ 2 bedrooms

Children-Friendly Pleasant Condo with Patio, Pool & Garden | Next to the Beach | Perfect for Remote Work

Wailea, Wailea-Makena, Hawaii, United States
$595$428
per night
Outstanding(131 ratings)
$595$428
per night
View deal
Condo Wailea
-66%
Sep 3 - Sep 10
Condo ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Big Condo with BBQ & Pool

Wailea, Wailea-Makena, Hawaii, United States
$1,411$478
per night
Outstanding(81 ratings)
$1,411$478
per night
View deal
Condo Wailea
-25%
Oct 4 - Oct 11
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with BBQ & Pool

Wailea, Wailea-Makena, Hawaii, United States
$745$580
per night
Outstanding(88 ratings)
$745$580
per night
View deal
Condo Wailea
Sep 3 - Sep 10
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Heated Pool, Yard & Barbecue | Mountain View

Wailea, Wailea-Makena, Hawaii, United States
$401
per night
Outstanding(9 ratings)
$401
per night
View deal
Condo Wailea
-28%
Jun 7 - Jun 14
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Terrace, Heated Pool & Garden | Mountain View

Wailea, Wailea-Makena, Hawaii, United States
$668$486
per night
Outstanding(53 ratings)
$668$486
per night
View deal
Condo Wailea
-53%
Jan 31 - Feb 7
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with Grill, Pool & Yard

Wailea, Wailea-Makena, Hawaii, United States
$680$484
per night
Outstanding(62 ratings)
$680$484
per night
View deal
Condo Wailea
-27%
Jun 2 - Jun 9
Condo ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Ample Condo with Pool & BBQ | Beach Nearby

Wailea, Wailea-Makena, Hawaii, United States
$883$677
per night
Outstanding(94 ratings)
$883$677
per night
View deal
Condo Wailea
-25%
May 8 - May 15
Condo ∙ 5 guests ∙ 1 bedroom

Condo with Private Pool, Grill & Terrace

Wailea, Wailea-Makena, Hawaii, United States
$229$208
per night
Outstanding(113 ratings)
$229$208
per night
View deal
Condo Wailea
May 3 - May 10
Condo ∙ 3 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$235
per night
Outstanding(74 ratings)
$235
per night
View deal
House Wailea
-35%
May 24 - May 31
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Vacation Home with Terrace, Barbecue & Yard | Mountain View | Good for Workation

Wailea, Wailea-Makena, Hawaii, United States
$1,198$742
per night
Outstanding(36 ratings)
$1,198$742
per night
View deal
House Wailea
-50%
Apr 20 - Apr 27
House ∙ 8 guests ∙ 4 bedrooms

House with BBQ, Patio & Sauna

Wailea, Wailea-Makena, Hawaii, United States
$2,238$1,201
per night
Outstanding(102 ratings)
$2,238$1,201
per night
View deal
Condo Wailea
Jun 28 - Jul 5
Condo ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Condo with Yard, Heated Pool & BBQ | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$314
per night
Outstanding(149 ratings)
$314
per night
View deal
Condo Wailea
Apr 30 - May 7
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with Pool, BBQ & Terrace

Wailea, Wailea-Makena, Hawaii, United States
$685
per night
Outstanding(89 ratings)
$685
per night
View deal

Apartments With Balconies or Patios

Condo  Wailea
Sep 29 - Oct 6
-37%
$407
$266
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with Terrace, Garden & Barbecue | Garden View

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
Dec 12 - Dec 19
-36%
$609
$415
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Family-Friendly Nice Condo with Heated Pool | Next to the Beach

4.9
Outstanding(123 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
House  Wailea
Jan 11 - Jan 18
$742
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Vacation Home with Terrace, Barbecue & Yard | Mountain View | Good for Workation

5.0
Outstanding(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
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Best Vacation Home Deals in Wailea

Save up to 58%

Serviced apartment Wailea
Aug 22 - Aug 29
-50%
$408
$239
per night
Serviced apartment ∙ 127 guests ∙ 3 bedrooms

Serviced Apartment with Pool, Garden & Barbeque

4.0
Very good
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Apr 9 - Apr 16
-58%
$542
$340
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Big Condo with Pool, Terrace & BBQ | Close to the Beach

4.8
Outstanding(68 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Sep 6 - Sep 13
-25%
$747
$556
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with Pool, Yard & Terrace

4.8
Outstanding(122 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

7,518 great rentals from 28 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
Jun 3 - Jun 10
$385
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool

5.0
Outstanding(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Jun 20 - Jun 27
$696
per night
House ∙ 7 guests ∙ 3 bedrooms

House with Patio, Yard & Private Pool

4.9
Outstanding(89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Aug 24 - Aug 31
-26%
$336
$299
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Spacious House with Terrace & Pool | Nature View | 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
Jun 28 - Jul 5
$248
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Family-Oriented Beautiful Condo with Barbeque, Yard & Pool | Beach Nearby

4.9
Outstanding(204 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Dec 1 - Dec 8
$226
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Family-Oriented Condo with Hot Tub, Barbeque & Pool

4.9
Outstanding(164 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 27 - Jun 3
$377
per night
Condo ∙ 6 guests ∙ 6 bedrooms

Child-Friendly Ample Condo with Garden, Terrace & Barbeque | City View | Suitable for Remote Work

5.0
Outstanding(109 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 $946
per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(49 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $946
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 $471
per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $471
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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Popular Rental Amenities in Wailea

  • Pool (6,158)
  • Air conditioning (6,642)
  • Kitchen (6,621)
  • Parking (301)
  • Balcony/patio (2,160)
  • WiFi (7,279)
  • Washing machine (5,296)
  • TV (6,683)
  • Microwave (5,701)
  • Dishwasher (4,329)
  • Grill (4,263)
  • No smoking (6,615)

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 January (1/24 – 1/31). Prices reach an average of $850 per night. Prices decrease in a week of September (9/20 – 9/27), where average prices are $462.

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 (2/8 – 2/15). Only 9% of the rentals are still available. On the contrary, only 36% 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 7,518 rentals
💳 Possible discounts up to 58%
🌙 Nightly prices starting at $187
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,229 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 $187 per night. $611 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $591 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,518 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 6,229 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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