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

Vacation rentals in Wailea

Browse 7,407 available vacation homes and compared across 30 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 7,407 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with hot tub, BBQ & garden | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a heated pool, hot tub, and family-friendly amenities, perfect for your next vacation getaway.
from $830
per night
Outstanding(32 ratings)
from $830
per night
View deal
Villa Wailea
Villa ∙ 10 guests ∙ 3 bedrooms

Family-oriented big villa with barbecue, hot tub & pool | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This Wailea villa features a pool, hot tub, and beach access, perfect for events and family gatherings with room for 10.
from $1,177
per night
Outstanding(148 ratings)
from $1,177
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, pool & garden | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo offers beach access, a pool, a kitchen, and parking, perfect for a memorable getaway with six guests.
from $404
per night
Outstanding(8 ratings)
from $404
per night
View deal
Condo Wailea
Condo ∙ 7 guests ∙ 2 bedrooms

Condo with barbeque, garden & patio | Mountain view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, hot tub, balcony with mountain views, and family-friendly amenities for up to seven guests.
from $532
per night
Outstanding(2 ratings)
from $532
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with terrace, heated pool & jacuzzi | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea-Makena condo features a heated pool, hot tub, kitchen, and balcony, perfect for relaxing with up to six guests.
from $429
per night
Very good(32 ratings)
from $429
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with barbecue, heated pool & hot tub | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a heated pool, hot tub, kitchen, and balcony, perfectly accommodating up to six guests.
from $292
per night
Very good(87 ratings)
from $292
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented condo with patio, pool & yard | Nature view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This waterfront condo in Kihei features a pool, spa, kitchen, and beach access, perfect for families seeking relaxation.
from $406
per night
Outstanding(41 ratings)
from $406
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with garden, BBQ & terrace | Nature view

Wailea, Wailea-Makena, Hawaii, United States
This waterfront condo in Wailea offers beach access, a pool, hot tub, and a balcony with mountain views, perfect for families.
from $1,171
per night
Outstanding(132 ratings)
from $1,171
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
This Kihei condo features a private pool, hot tub, sauna, and a spacious yard, perfect for a vacation with family or friends.
from $430
per night
Outstanding(86 ratings)
from $430
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Child-friendly condo with heated pool, terrace & barbeque | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers a heated pool, kitchen, and balcony, perfect for families seeking a memorable getaway.
from $312
per night
Outstanding(1 rating)
from $312
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers pool access, a hot tub, a kitchen, and direct beach access, accommodating up to six guests.
from $868
per night
Outstanding(17 ratings)
from $868
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Family-friendly condo with barbecue & pool | Beach view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This condo in Wailea offers beach access, a pool, sea views, and a kitchen, perfect for family gatherings and events.
from $319
per night
Outstanding(62 ratings)
from $319
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool, yard & grill | Water view

Wailea, Wailea-Makena, Hawaii, United States
This waterfront Wailea condo offers beach access, stunning sea views, a pool, and a balcony, perfect for family gatherings.
from $282
per night
Outstanding(3 ratings)
from $282
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Fully equipped wonderful condo with jacuzzi, grill & pool | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, hot tub, balcony, and parking, accommodating up to eight guests for a perfect getaway.
from $475
per night
Outstanding(111 ratings)
from $475
per night
View deal
Condo Wailea
Condo ∙ 8 guests ∙ 3 bedrooms

Children-friendly condo with BBQ, heated pool & yard | City view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This waterfront condo in Kihei offers direct beach access, a heated pool, and a balcony, perfect for family vacations.
from $918
per night
Excellent(27 ratings)
from $918
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Wailea
from $562
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with pool, hot tub & grill | Water view

4.9
Outstanding(122 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $823
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with patio, grill & hot tub

4.9
Outstanding(77 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
House  Wailea
from $1,793
per night
House ∙ 12 guests ∙ 4 bedrooms

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

5.0
Outstanding(98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Condo  Wailea
from $579
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly condo with grill, pool & yard | City view | Close to the beach

5.0
Outstanding(10 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $384
per night
Condo ∙ 8 guests ∙ 3 bedrooms

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

3.7
Good(70 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $271
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, barbeque & private pool | Mountain view

4.9
Outstanding(91 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation Rentals With Saunas

Condo  Wailea
from $234
per night
Condo ∙ 4 guests ∙ 1 bedroom

Family-oriented condo with hot tub, BBQ & pool | Water view | Next to the beach

5.0
Outstanding(98 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
Condo  Wailea
from $153
per night
Condo ∙ 2 guests ∙ 1 bedroom

Children-friendly lovely condo with sauna, garden & BBQ | Water view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
Condo  Wailea
from $261
per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

4.7
Excellent(27 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Sauna
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Wailea offering exceptional value for money

Condo Wailea
from $350
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful condo with heated pool, hot tub & barbecue | Nature view | Next to the beach

4.0
Very good(32 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $283
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

4.9
Outstanding(13 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $314
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with BBQ & pool | Beach view

4.7
Excellent(73 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 $421
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Fully equipped beautiful condo with patio, pool & yard | Mountain view | Next to the beach

4.7
Excellent(28 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $261
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped condo with heated pool & barbeque | Nature view | Next to the beach

4.8
Outstanding(11 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $400
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with terrace & pool | Nature view

5.0
Outstanding(6 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 $1,252
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 $353
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 $228
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 (5,650)
  • Air conditioning (5,739)
  • Kitchen (5,841)
  • Parking (273)
  • Balcony/patio (2,565)
  • WiFi (5,896)
  • Washing machine (5,050)
  • TV (5,857)
  • Microwave (4,979)
  • Dishwasher (4,512)
  • Grill (4,416)
  • No smoking (5,652)

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, one-third 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 (2/6 – 2/13). Prices reach an average of $920 per night. Prices decrease in a week of August (8/29 – 9/5), where average prices are $729.

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 May (5/8 – 5/15). Only 25% of the rentals are still available. On the contrary, only 17% of vacation rentals are unavailable in August (8/15 – 8/22).

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 7,407 rentals
🌙 Nightly prices starting at $155
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,365 homes
22 reviews
Wailea vacation rentals have an average rating of 4.7/5 on 22 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 $155 per night. Nightly prices for condos are $649 on average. Apartment rentals in Wailea cost on average $818 per night.

How many vacation homes are available to book in Wailea?

There are 7,407 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 6,365 vacation homes across 30 providers in Wailea.

Are dogs allowed in vacation homes in Wailea?

Absolutely, there are 161 vacation rentals in Wailea that allow dogs , with an average price of $1,974 per night.

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