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

Vacation rentals in Wailea

Browse 6,329 available vacation homes and compared across 29 trusted partners
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Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 6,146 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Condo with patio, barbeque & garden

Wailea, Wailea-Makena, Hawaii, United States
from $164
per night
Very good(114 ratings)
from $164
per night
View deal
Villa Wailea
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with garden, patio & grill

Wailea, Wailea-Makena, Hawaii, United States
from $1,043
per night
Outstanding(125 ratings)
from $1,043
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with hot tub, garden & pool | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $573
per night
Excellent(190 ratings)
from $573
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with patio, sauna & private pool

Wailea, Wailea-Makena, Hawaii, United States
from $241
per night
Outstanding(85 ratings)
from $241
per night
View deal
House Wailea
House ∙ 6 guests ∙ 3 bedrooms

House with garden, hot tub & BBQ | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $1,037
per night
Outstanding(98 ratings)
from $1,037
per night
View deal
Condo Wailea
Condo ∙ 3 guests ∙ 1 bedroom

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

Wailea, Wailea-Makena, Hawaii, United States
from $205
per night
Outstanding(48 ratings)
from $205
per night
View deal
Serviced apartment Wailea
Serviced apartment ∙ 6 guests ∙ 2 bedrooms

Serviced apartment with garden, barbecue & pool

Wailea, Wailea-Makena, Hawaii, United States
from $202
per night
Very good
from $202
per night
View deal
House Wailea
House ∙ 4 guests ∙ 2 bedrooms

Family-friendly charming house with pool, garden & BBQ | Close to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $270
per night
Outstanding(53 ratings)
from $270
per night
View deal
Villa Wailea
Villa ∙ 10 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $1,018
per night
Outstanding(91 ratings)
from $1,018
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped charming condo with pool | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
from $263
per night
Outstanding(4 ratings)
from $263
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool & grill | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $248
per night
Outstanding(3 ratings)
from $248
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with pool & BBQ

Wailea, Wailea-Makena, Hawaii, United States
from $441
per night
Very good(26 ratings)
from $441
per night
View deal
House Wailea
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with barbecue, jacuzzi & terrace

Wailea, Wailea-Makena, Hawaii, United States
from $1,107
per night
Outstanding(43 ratings)
from $1,107
per night
View deal
House Wailea
House ∙ 12 guests ∙ 4 bedrooms

Vacation home with yard, terrace & private pool | Mountain view | Perfect for remote work

Wailea, Wailea-Makena, Hawaii, United States
from $2,164
per night
Outstanding(87 ratings)
from $2,164
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with patio, pool & barbecue

Wailea, Wailea-Makena, Hawaii, United States
from $862
per night
from $862
per night
View deal

Vacation rentals with a balcony

Condo  Wailea
from $215
per night
Condo ∙ 4 guests ∙ 1 bedroom

Fully equipped nice condo with pool & barbeque | Beach nearby

4.4
Very good(47 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $292
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Mountain view

4.9
Outstanding(89 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $360
per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

5.0
Outstanding(111 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
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Vacation houses with Balconies or Patios

Condo  Wailea
from $251
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with BBQ, pool & patio | Nature view | Next to the beach

4.3
Very good(33 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $236
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with pool, hot tub & barbecue | Nature view | Beach nearby

4.6
Excellent(24 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $377
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool, patio & yard

4.9
Outstanding(183 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

Condo  Wailea
-39%
$862
from $524
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, pool & barbecue | Nature view

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Cabin  Wailea
from $298
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbecue, yard & terrace

4.6
Excellent(44 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $207
per night
Condo ∙ 4 guests ∙ 1 bedroom

Fully equipped pleasant condo with heated pool, jacuzzi & BBQ | Beach nearby

4.8
Outstanding(58 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Wailea offering exceptional value for money

Condo Wailea
from $330
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly wonderful condo with heated pool & jacuzzi | Next to the beach

4.9
Outstanding(55 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $324
per night
Condo ∙ 5 guests ∙ 2 bedrooms

Children-friendly condo with heated pool, yard & barbeque | Mountain view | Beach nearby | Suitable for remote work

5.0
Outstanding(58 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
from $1,384
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Fully equipped wonderful villa with heated pool, barbeque & jacuzzi | Close to the beach

5.0
Outstanding(118 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Top-Rated Vacation rentals in Wailea

Book the highest-rated Wailea vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Wailea
from $557
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Children-friendly pleasant condo with terrace, jacuzzi & barbecue | Suitable for remote work

4.9
Outstanding(70 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $604
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard, patio & grill | Nature view

4.8
Outstanding(90 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $621
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with sauna, barbecue & jacuzzi | Nature view

4.9
Outstanding(132 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Wailea

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 $1,107
per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(65 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 $384
per night
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 $287
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

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Popular Features & Amenities in Wailea

  • Pool (5,578)
  • Air conditioning (5,700)
  • Kitchen (5,828)
  • Parking (278)
  • Balcony/patio (2,559)
  • WiFi (5,941)
  • Washing machine (4,837)
  • TV (5,833)
  • Microwave (5,044)
  • Dishwasher (4,513)
  • Grill (4,407)
  • No smoking (5,639)

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 March (3/14 – 3/21). Prices reach an average of $611 per night. Prices decrease in a week of December (12/13 – 12/20), where average prices are $549.

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 November (11/7 – 11/14). Only 14% of the rentals are still available. On the contrary, only 28% of vacation rentals are unavailable in May (5/30 – 6/6).

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 6,146 rentals
🌙 Nightly prices starting at $195
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 5,478 homes
18 reviews
Wailea vacation rentals have an average rating of 4.3/5 on 18 reviews left by travelers.

Frequently Asked Questions

What is the price per night for a vacation rental in Wailea?

Prices for vacation rentals in Wailea start from $195 per night. Nightly prices for condos are $638 on average. Apartment rentals in Wailea cost on average $609 per night.

How many vacation homes are available to book in Wailea?

There are 6,146 vacation rentals in Wailea to browse and rent for your next trip.

What amenities are most popular for vacation rentals in Wailea?

Travelers search for Pool, Air conditioning, and Kitchen when booking a vacation rental in Wailea.

How many vacation rentals with a pool are in Wailea?

There are 5,478 vacation homes across 29 providers in Wailea.

Are dogs allowed in vacation homes in Wailea?

Absolutely, there are 184 vacation rentals in Wailea that allow dogs , with an average price of $2,113 per night.

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