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

Vacation rentals in Wailea

Browse 7,165 available vacation homes and compared across 30 trusted partners
Anytime
Guests
Anytime
Guests

Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 7,165 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with heated pool & jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
This Wailea-Makena condo features a heated pool, hot tub, kitchen, and balcony, perfect for a memorable getaway with friends.
from $345
per night
Outstanding(75 ratings)
from $345
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
This Kihei condo offers a pool, kitchen, and parking, accommodating up to six for an unforgettable vacation experience.
from $672
per night
Outstanding(24 ratings)
from $672
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 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 $893
per night
Outstanding(17 ratings)
from $893
per night
View deal
Villa Wailea
Villa ∙ 10 guests ∙ 4 bedrooms

Villa with terrace, BBQ & hot tub | Mountain view | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
This Wailea villa features stunning mountain views, a heated pool, a hot tub, and accommodates up to 10 guests for unforgettable stays.
from $1,077
per night
Outstanding(41 ratings)
from $1,077
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features beach access, a heated pool, a hot tub, and a yard, perfect for a family getaway for six.
from $246
per night
Outstanding(261 ratings)
from $246
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with private pool, hot tub & grill

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a private pool, kitchen, hot tub, and yard, making it an ideal retreat for up to six guests.
from $355
per night
Outstanding(186 ratings)
from $355
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

Condo with grill, yard & heated pool | Mountain view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers beachfront access, mountain views, a heated pool, and a kitchen, perfect for a family getaway.
from $359
per night
Outstanding(54 ratings)
from $359
per night
View deal
House Wailea
House ∙ 15 guests ∙ 5 bedrooms

Wonderful vacation home with barbeque & private pool | Good for workation | Pets are welcome

Wailea, Wailea-Makena, Hawaii, United States
This house rental in Wailea accommodates 15 guests, featuring a private pool, kitchen, and parking, welcoming pets for your stay.
from $344
per night
from $344
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace, BBQ & pool | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This waterfront condo in Wailea features a pool, kitchen, balcony, and beach access, accommodating up to six guests.
from $640
per night
Outstanding(11 ratings)
from $640
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo offers beach access, a pool, a kitchen, and a balcony perfect for family gatherings or events.
from $304
per night
Outstanding(7 ratings)
from $304
per night
View deal
Condo Wailea
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, yard & terrace | Garden view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea-Makena condo offers a pool, hot tub, beach access, and a balcony with sea views, perfect for a family getaway.
from $375
per night
Excellent(6 ratings)
from $375
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, beach access, and a balcony with sea views, perfect for family getaways and events.
from $279
per night
Outstanding(13 ratings)
from $279
per night
View deal
House Wailea
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with garden, terrace & grill | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a pool, hot tub, kitchen, yard, and beach access, accommodating up to 10 guests comfortably.
from $1,303
per night
Outstanding(109 ratings)
from $1,303
per night
View deal
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

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

Wailea, Wailea-Makena, Hawaii, United States
This Wailea condo features a pool, kitchen, yard, and balcony, perfect for a memorable getaway with family or friends.
from $312
per night
from $312
per night
View deal
House Wailea
House ∙ 5 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
This Wailea house rental features a kitchen, yard, balcony, and parking, perfect for families seeking a memorable getaway.
from $615
per night
Outstanding(38 ratings)
from $615
per night
View deal

Vacation Houses With Pools

We use AI to generate the short summary in each offer below, check full description before booking.
Condo  Wailea
from $250
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with yard, hot tub & heated pool | City view

4.9
Outstanding(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Pool
View deal
House  Wailea
from $139
per night
House ∙ 4 guests ∙ 1 bedroom

Vacation home with pool, hot tub & grill | City view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
Pool
View deal
Condo  Wailea
from $668
per night
Condo ∙ 12 guests ∙ 4 bedrooms

Fully equipped lovely condo with pool, hot tub & yard | Next to the beach | Good for workation

Wailea, Wailea-Makena, Hawaii, United States
Pool
View deal
See all offers

Vacation rentals and apartments with air conditioning

We use AI to generate the short summary in each offer below, check full description before booking.
Condo  Wailea
from $296
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Children-friendly wonderful condo with pool & BBQ | Water view | Beach nearby

4.9
Outstanding(115 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $502
per night
Condo ∙ 8 guests ∙ 2 bedrooms

Condo with pool & BBQ

4.6
Excellent(7 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Condo  Wailea
from $498
per night
Condo ∙ 6 guests ∙ 2 bedrooms

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

4.8
Outstanding(42 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

We use AI to generate the short summary in each offer below, check full description before booking.
Condo  Wailea
from $182
per night
Condo ∙ 4 guests ∙ 1 bedroom

Children-friendly condo with pool, jacuzzi & patio | Garden view | Close to the beach | Suitable for remote work

4.9
Outstanding(21 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $407
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with barbecue, pool & terrace

4.9
Outstanding(79 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Condo  Wailea
from $395
per night
Condo ∙ 5 guests ∙ 2 bedrooms

Fully equipped pleasant condo with pool, barbeque & hot tub | Nature view

5.0
Outstanding(2 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 $251
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly condo with pool & garden | Beach nearby

5.0
Outstanding(13 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $299
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with pool & barbeque | Sea view | Close to the beach

4.9
Outstanding(139 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $527
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with barbecue, patio & heated pool | Nature view

3.7
Good(3 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 $192
per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with pool, BBQ & patio | Good for workation

4.7
Excellent(69 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
from $300
per night
House ∙ 4 guests ∙ 2 bedrooms

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

4.8
Outstanding(56 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Condo Wailea
from $479
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with terrace & pool | Nature view

5.0
Outstanding(7 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 $1,269
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 $306
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 $173
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea, Wailea-Makena, Hawaii, United States
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 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 $999 per night. Prices decrease in a week of September (9/26 – 10/3), where average prices are $822.

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 August (8/21 – 8/28). Only 9% of the rentals are still available. On the contrary, only 11% of vacation rentals are unavailable in September (9/19 – 9/26).

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 7,165 rentals
🌙 Nightly prices starting at $121
⭐ Popular amenities Pool, Air conditioning and Kitchen
🏊 Vacation rentals with pools 6,168 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 $121 per night. Nightly prices for condos are $692 on average. Apartment rentals in Wailea cost on average $1,147 per night.

How many vacation homes are available to book in Wailea?

There are 7,165 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 6,168 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 $2,032 per night.

Top cities to visit

Similar vacation rentals nearby

Most Popular Destinations

Show more
image-tag