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

Vacation rentals in Wailea

Browse 6,102 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 6,102 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with hot tub, barbeque & pool

Wailea, Wailea-Makena, Hawaii, United States
from $505
per night
Outstanding(102 ratings)
from $505
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $331
per night
Outstanding(55 ratings)
from $331
per night
View deal
House Wailea
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with barbecue, jacuzzi & terrace

Wailea, Wailea-Makena, Hawaii, United States
from $1,109
per night
Outstanding(43 ratings)
from $1,109
per night
View deal
Cabin Wailea
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbecue, yard & terrace | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $299
per night
Excellent(44 ratings)
from $299
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 $1,051
per night
Outstanding(98 ratings)
from $1,051
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 $2,168
per night
Outstanding(87 ratings)
from $2,168
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with jacuzzi, heated pool & patio | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
from $453
per night
Outstanding(32 ratings)
from $453
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 $570
per night
Excellent(190 ratings)
from $570
per night
View deal
Villa Wailea
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with garden, patio & grill

Wailea, Wailea-Makena, Hawaii, United States
from $1,061
per night
Outstanding(125 ratings)
from $1,061
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped charming condo with yard, heated pool & hot tub

Wailea, Wailea-Makena, Hawaii, United States
from $285
per night
Outstanding(31 ratings)
from $285
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with patio, yard & private pool | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
from $435
per night
Outstanding(85 ratings)
from $435
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with yard, pool & BBQ | Nature view

Wailea, Wailea-Makena, Hawaii, United States
from $522
per night
Outstanding(1 rating)
from $522
per night
View deal
House Wailea
House ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
from $292
per night
Excellent(70 ratings)
from $292
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented condo with heated pool, garden & BBQ | Nature view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
from $273
per night
Outstanding(172 ratings)
from $273
per night
View deal
House Wailea
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque, yard & private pool | Sea view

Wailea, Wailea-Makena, Hawaii, United States
from $480
per night
from $480
per night
View deal

Vacation rentals with a balcony

Condo  Wailea
from $278
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Nature view

4.9
Outstanding(88 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony
View deal
Condo  Wailea
from $216
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 $366
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 rentals and apartments with air conditioning

Condo  Wailea
from $265
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with barbeque, jacuzzi & heated pool

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Villa  Wailea
from $1,388
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
Air conditioning
View deal
Condo  Wailea
from $240
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with patio, sauna & private pool

4.8
Outstanding(85 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Condo  Wailea
from $217
per night
Condo ∙ 4 guests ∙ 1 bedroom

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

4.3
Very good(33 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $264
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 $286
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, yard & patio | Nature view | Suitable for remote work

4.8
Outstanding(239 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Wailea offering exceptional value for money

Condo Wailea
from $426
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with hot tub, patio & pool

5.0
Outstanding(24 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
from $1,049
per night
Villa ∙ 10 guests ∙ 3 bedrooms

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

5.0
Outstanding(177 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $573
per night
House ∙ 5 guests ∙ 2 bedrooms

Children-friendly charming vacation home with barbeque & yard | Nature view | Good for workation

5.0
Outstanding(35 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 $282
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly lovely condo with garden, sauna & barbecue | Beach nearby | Perfect for remote work

4.6
Excellent(14 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $302
per night
Condo ∙ 8 guests ∙ 2 bedrooms

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

4.9
Outstanding(58 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $193
per night
Condo ∙ 3 guests ∙ 1 bedroom

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

4.9
Outstanding(48 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 $1,099
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 $372
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 $223
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 (5,465)
  • Air conditioning (5,458)
  • Kitchen (5,566)
  • Parking (280)
  • Balcony/patio (2,547)
  • WiFi (5,745)
  • Washing machine (4,705)
  • TV (5,687)
  • Microwave (4,865)
  • Dishwasher (4,453)
  • Grill (4,360)
  • No smoking (5,468)

Finding a rental with a pool is easy in Wailea. Nearly all 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 February (2/14 – 2/21). Prices reach an average of $605 per night. Prices decrease in a week of December (12/6 – 12/13), where average prices are $545.

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 October (10/24 – 10/31). Only 19% of the rentals are still available. On the contrary, only 27% of vacation rentals are unavailable in December (12/13 – 12/20).

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 6,102 rentals
🌙 Nightly prices starting at $214
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 5,491 homes
16 reviews
Wailea vacation rentals have an average rating of 4.3/5 on 16 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 $214 per night. Nightly prices for condos are $636 on average. Apartment rentals in Wailea cost on average $546 per night.

How many vacation homes are available to book in Wailea?

There are 6,102 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 5,491 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 $2,098 per night.

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