Condos in Wailea - HomeToGo base64Hash Condos in Wailea - HomeToGo

Condos in Wailea

Find 7,352 available house rentals from 28 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Wailea

Find your perfect vacation rental in Wailea from just $165 per night!

Condo Wailea
May 10 - May 17
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with Terrace, Pool & Grill | City View

Wailea, Wailea-Makena, Hawaii, United States
$603
per night
Excellent(20 ratings)
$603
per night
View deal
Condo Wailea
-22%
Jan 30 - Feb 6
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
-27%
Jan 25 - Feb 1
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with Pool & Grill | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$750$566
per night
Very good(28 ratings)
$750$566
per night
View deal
Condo Wailea
-24%
May 13 - May 20
Condo ∙ 10 guests ∙ 4 bedrooms

Condo with Pool, Patio & Grill | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$1,613$1,200
per night
Outstanding(58 ratings)
$1,613$1,200
per night
View deal
Condo Wailea
-37%
May 1 - May 8
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Condo with Garden, Patio & Pool | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$428$266
per night
Excellent(47 ratings)
$428$266
per night
View deal
Condo Wailea
-25%
May 10 - May 17
Condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$254$197
per night
Outstanding(54 ratings)
$254$197
per night
View deal
Condo Wailea
Jun 29 - Jul 6
Condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$246
per night
Outstanding(205 ratings)
$246
per night
View deal
Condo Wailea
May 17 - May 24
Condo ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Condo with Pool & Barbecue | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$365
per night
Outstanding(66 ratings)
$365
per night
View deal
House Wailea
Apr 12 - Apr 19
House ∙ 8 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Patio, Grill & Yard

Wailea, Wailea-Makena, Hawaii, United States
$1,135
per night
Outstanding(151 ratings)
$1,135
per night
View deal
Condo Wailea
Nov 7 - Nov 14
Condo ∙ 7 guests ∙ 4 bedrooms

Condo with Terrace, BBQ & Garden | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$526
per night
Outstanding(102 ratings)
$526
per night
View deal
Condo Wailea
-32%
Mar 27 - Apr 3
Condo ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Nice Condo with Terrace, BBQ & Pool | Nature View | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$707$496
per night
Excellent(23 ratings)
$707$496
per night
View deal
Condo Wailea
-28%
May 10 - May 17
Condo ∙ 5 guests ∙ 1 bedroom

Condo with Private Pool, Grill & Terrace

Wailea, Wailea-Makena, Hawaii, United States
$221$165
per night
Outstanding(112 ratings)
$221$165
per night
View deal
Condo Wailea
-32%
Jan 28 - Feb 4
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with Grill, Pool & Yard

Wailea, Wailea-Makena, Hawaii, United States
$668$474
per night
Outstanding(63 ratings)
$668$474
per night
View deal
Condo Wailea
Jul 12 - Jul 19
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
$316
per night
Outstanding(169 ratings)
$316
per night
View deal
Condo Wailea
May 17 - May 24
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool & BBQ | Mountain View

Wailea, Wailea-Makena, Hawaii, United States
$461
per night
Outstanding(61 ratings)
$461
per night
View deal

Apartments With Balconies or Patios

Condo  Wailea
Sep 29 - Oct 6
-37%
$406
$267
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%
$615
$393
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
$813
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
See all offers

Best Vacation Home Deals in Wailea

Save up to 58%

Condo Wailea
Apr 9 - Apr 16
-58%
$795
$361
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
Apr 26 - May 3
-46%
$3,506
$1,948
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo with Heated Pool, BBQ & Yard

4.7
Excellent(50 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Sep 6 - Sep 13
-25%
$713
$571
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

7,352 great rentals from 28 partner websites, such as Abritel 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
May 17 - May 24
-34%
$298
$201
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Beautiful Condo with Patio, Barbeque & Pool | Mountain View | Close to the Beach

4.7
Excellent(192 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Jan 6 - Jan 13
$800
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-Friendly House with Patio, Barbeque & Garden | Nature View

5.0
Outstanding(155 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Jun 7 - Jun 14
-29%
$749
$428
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Pool, Barbecue & Terrace | Nature View

5.0
Outstanding(6 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 18 - Apr 25
$996
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Terrace, Private Pool & Yard

4.9
Outstanding(96 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
May 10 - May 17
-32%
$371
$277
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Condo with Pool & BBQ | Beach Nearby

4.9
Outstanding(72 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
Sep 20 - Sep 27
-67%
$705
$378
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Charming Condo with Barbecue & Pool | Nature View | Beach Nearby

4.9
Outstanding(59 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 $1,018
per night
HomeToGo
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(48 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $1,018
per night
Condo ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(48 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 $472
per night
HomeToGo
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
from $472
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

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

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

Price clarity, no surprises

Price clarity, no surprises

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

Smart search made simple

Smart search made simple

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 (6,082)
  • Air conditioning (6,591)
  • Kitchen (6,554)
  • Parking (289)
  • Balcony/patio (2,179)
  • WiFi (7,132)
  • Washing machine (5,151)
  • TV (6,660)
  • Microwave (5,778)
  • Dishwasher (4,392)
  • Grill (4,256)
  • No smoking (6,575)

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 $784 per night. Prices decrease in a week of September (9/6 – 9/13), where average prices are $465.

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 15% of the rentals are still available. On the contrary, only 34% 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 7,352 rentals
💳 Possible discounts up to 72%
🌙 Nightly prices starting at $165
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,046 homes
322,696 reviews
Wailea vacation rentals have an average rating of 4.6/5 on 322,696 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 $165 per night. $615 is the average nightly price for condos in Wailea. Apartment rentals in Wailea cost $601 per night on average.

How many vacation rentals are available for booking in Wailea?

Currently there are 7,352 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 6,046 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.

Top cities to visit

Vacation Destinations Near Wailea

Find the perfect Wailea home to match your style

image-tag