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

Vacation rentals in Wailea-Makena

Browse 5,622 available vacation homes and compared across 27 trusted partners
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Guests
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  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • Balcony/patio
    • Kitchen
    • WiFi
    • Washing machine
    • Parking
    • TV
    • Microwave
    • Dishwasher
    • Hot tub
    • Yard
    • Fireplace
    • Crib
    • Sauna
    Show more

  • Accommodation type

    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Wailea-Makena

Discover your ideal Wailea-Makena vacation rental with real-time comparisons of 5,622 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Wailea-Makena
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with jacuzzi, heated pool & patio | Mountain view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo offers a heated pool, hot tub, kitchen, and mountain views, perfect for families of up to 8.
from $505
per night
Outstanding(33 ratings)
from $505
per night
View deal
Condo Wailea-Makena
Condo ∙ 6 guests ∙ 2 bedrooms

Fully equipped condo with pool, barbeque & hot tub | Close to the beach

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo features a pool, spa, kitchen, hot tub, and balcony, accommodating up to six for an unforgettable getaway.
from $332
per night
Excellent(46 ratings)
from $332
per night
View deal
Condo Wailea-Makena
Condo ∙ 8 guests ∙ 2 bedrooms

Condo with yard, BBQ & terrace | Nature view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo offers a pool, kitchen, yard, and parking, perfect for families seeking a memorable vacation for up to 8.
from $670
per night
Outstanding(225 ratings)
from $670
per night
View deal
Condo Wailea-Makena
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea-Makena, Maui County, 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 $316
per night
Outstanding(245 ratings)
from $316
per night
View deal
House Wailea-Makena
House ∙ 6 guests ∙ 3 bedrooms

House with garden, hot tub & BBQ | Nature view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea-Makena house rental features a private pool, hot tub, and yard, perfect for a memorable getaway with friends or family.
from $1,020
per night
Outstanding(104 ratings)
from $1,020
per night
View deal
Condo Wailea-Makena
Condo ∙ 8 guests ∙ 3 bedrooms

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

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo features beach access, a pool, a kitchen, and a balcony, accommodating up to 8 guests for an unforgettable stay.
from $375
per night
Good(68 ratings)
from $375
per night
View deal
Condo Wailea-Makena
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with yard, pool & barbecue | Nature view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo features a pool, kitchen, balcony, and parking, perfect for a relaxing getaway with friends or family.
from $202
per night
from $202
per night
View deal
Condo Wailea-Makena
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with pool, terrace & hot tub | Mountain view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea-Makena condo features a pool, hot tub, balcony with mountain views, and a yard, perfect for up to six guests.
from $571
per night
Outstanding(54 ratings)
from $571
per night
View deal
Condo Wailea-Makena
Condo ∙ 4 guests ∙ 3 bedrooms

Family-friendly wonderful condo with yard, jacuzzi & patio | City view | Next to the beach | Suitable for remote work

Wailea-Makena, Maui County, Hawaii, United States
This waterfront condo in Wailea offers beach access, a heated pool, hot tub, and a family-friendly yard for unforgettable vacations.
from $218
per night
Outstanding(13 ratings)
from $218
per night
View deal
Villa Wailea-Makena
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with garden, patio & grill

Wailea-Makena, Maui County, Hawaii, United States
This villa in Wailea features a pool, hot tub, and beach access, perfect for family gatherings by the waterfront.
from $1,306
per night
Outstanding(125 ratings)
from $1,306
per night
View deal
Villa Wailea-Makena
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with terrace, hot tub & grill | Garden view

Wailea-Makena, Maui County, Hawaii, United States
This villa in Wailea features a private pool, hot tub, and beach access, perfect for families seeking a waterfront getaway.
from $4,393
per night
Outstanding(3 ratings)
from $4,393
per night
View deal
Apartment Wailea-Makena
Apartment ∙ 4 guests ∙ 1 bedroom

Family-oriented lovely rental apartment with barbecue, hot tub & pool | Suitable for remote work

Wailea-Makena, Maui County, Hawaii, United States
This Wailea apartment offers beach access, a pool, a hot tub, and a balcony, perfect for a family getaway of up to four.
from $389
per night
from $389
per night
View deal
Condo Wailea-Makena
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool & grill | Beach view

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo features a pool, beach access, and a balcony with sea views, perfect for family getaways and events.
from $429
per night
Outstanding(12 ratings)
from $429
per night
View deal
Apartment Wailea-Makena
Apartment ∙ 6 guests ∙ 2 bedrooms

Child-friendly rental apartment with garden, jacuzzi & BBQ | Sea view | Beach nearby | Perfect for remote work

Wailea-Makena, Maui County, Hawaii, United States
This ocean-view apartment in Wailea-Makena features a pool, hot tub, kitchen, and beach access for unforgettable family getaways.
from $352
per night
Excellent(53 ratings)
from $352
per night
View deal
Condo Wailea-Makena
Condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea-Makena, Maui County, Hawaii, United States
This Wailea condo features a pool, kitchen, balcony, and parking, perfect for a memorable stay with up to six guests.
from $279
per night
Outstanding(5 ratings)
from $279
per night
View deal

Vacation rentals and apartments with air conditioning

Condo Wailea-Makena
from $455
per night
Condo ∙ 8 guests ∙ 2 bedrooms

Condo with pool, jacuzzi & grill | Garden view | Good for workation

5.0
Outstanding
Wailea-Makena, Maui County, Hawaii, United States
Air conditioning
View deal
Villa Wailea-Makena
from $793
per night
Villa ∙ 10 guests ∙ 3 bedrooms

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

4.9
Outstanding(148 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Air conditioning
View deal
Condo Wailea-Makena
from $335
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with heated pool & jacuzzi | Nature view

4.9
Outstanding(73 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Air conditioning
View deal
See all offers

Vacation houses with Balconies or Patios

Cabin Wailea-Makena
from $309
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbecue, yard & terrace | Nature view

4.6
Excellent(45 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Balcony/Patio
View deal
House Wailea-Makena
from $1,655
per night
House ∙ 12 guests ∙ 4 bedrooms

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

5.0
Outstanding(90 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Balcony/Patio
View deal
Condo Wailea-Makena
from $378
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with hot tub, pool & patio

5.0
Outstanding(106 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Balcony/Patio
View deal
See all offers

Vacation Rentals With Fireplaces

Villa Wailea-Makena
from $1,778
per night
Villa ∙ 7 guests ∙ 3 bedrooms

Child-friendly villa with terrace, hot tub & grill | Water view | Beach nearby | Perfect for remote work

5.0
Outstanding(13 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Fireplace
View deal
House Wailea-Makena
from $1,383
per night
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped house with hot tub, garden & heated pool | Garden view | Close to the beach

5.0
Outstanding(1 rating)
Wailea-Makena, Maui County, Hawaii, United States
Fireplace
View deal
Villa Wailea-Makena
from $1,650
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with hot tub, barbecue & fast internet | Water view | Suitable for remote work

5.0
Outstanding(10 ratings)
Wailea-Makena, Maui County, Hawaii, United States
Fireplace
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Wailea-Makena offering exceptional value for money

Condo Wailea-Makena
from $421
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with barbeque, patio & fast internet | Water view

4.8
Outstanding(14 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal
Condo Wailea-Makena
from $346
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with garden, barbecue & jacuzzi | Garden view

4.4
Very good(9 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal
Condo Wailea-Makena
from $280
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool & grill | Nature view

5.0
Outstanding(3 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal

Top-Rated Vacation rentals in Wailea-Makena

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

Condo Wailea-Makena
from $693
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Family-friendly condo with pool, barbecue & hot tub

4.9
Outstanding(90 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal
Condo Wailea-Makena
from $258
per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool, garden & barbecue | Nature view | Suitable for remote work

4.9
Outstanding(79 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal
Condo Wailea-Makena
from $518
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with pool, patio & yard | Nature view

5.0
Outstanding(74 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal

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

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-Makena
from $917
per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(65 ratings)
Wailea-Makena, Maui County, 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-Makena
from $503
per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(113 ratings)
Wailea-Makena, Maui County, 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-Makena
from $289
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding(95 ratings)
Wailea-Makena, Maui County, Hawaii, United States
View deal

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Popular Features & Amenities in Wailea-Makena

  • Pool (5,036)
  • Air conditioning (5,136)
  • Balcony/patio (2,403)
  • Kitchen (5,162)
  • WiFi (5,338)
  • Washing machine (4,318)
  • Parking (263)
  • TV (5,243)
  • Microwave (4,554)
  • No smoking (5,123)
  • Dishwasher (4,127)
  • Grill (3,968)

You will find a great selection of accommodations to choose from if you are looking for a rental including a pool in Wailea-Makena. Also, more Condo have pools than any other type of accommodation. They are a great choice if you go in a group of 5, as that is the number of people they can usually accommodate. If you would also like to be close to the water, nearly half of the accommodations providing a pool are within 2 miles of the waterfront.

Price and Availability Index in Wailea-Makena

Click on any bar to see price and availability information

Vacation Rental Price Information in Wailea-Makena

We gathered the average prices for accommodations in Wailea-Makena for the next year. The most expensive month to visit Wailea-Makena is December (12/19 – 12/26) However, in September (9/26 – 10/3), prices decrease to an average of $776 per night.

Rental availability information in Wailea-Makena

The graph above shows the typical availability of vacation rentals in Wailea-Makena. The week with the highest booking rate is in December (12/26 – 1/2). Only 21% of the rentals are still available. People tend to travel less to Wailea-Makena during a week in May (5/23 – 5/30) when only 17% of the rentals are booked.

Enjoy Wailea's great food and festivals with vacation rentals

The resort town of Wailea is known as a romantic destination marked by white sand beaches and spectacular scenic views. Resorts dot the town, along with abundant condo communities and several expansive mansions. Ideal for a romantic getaway, Wailea vacation rentals are perfect for experiencing Maui's finest food, nightlife and idyllic surroundings.

Information about vacation rentals in Wailea-Makena

🏡 Vacation rentals available 5,622 rentals
🌙 Nightly prices starting at $184
⭐ Popular amenities Pool, Air conditioning and Balcony/Patio
🏊 Vacation rentals with pools 5,040 homes
20 reviews
Wailea-Makena vacation rentals have an average rating of 4.4/5 on 20 reviews left by travelers.

Frequently Asked Questions

What is the typical nightly price for a vacation home in Wailea-Makena?

The price of a night's stay in Wailea-Makena starts at $184. Average prices for condos are $682 per night. Apartment rentals in Wailea-Makena cost on average $592 per night.

How many vacation homes are available for booking in Wailea-Makena?

There are 5,622 vacation homes to choose from for your next trip.

What are the most popular amenities for vacation rentals in Wailea-Makena?

Usually travelers look for Air conditioning, Pool, and Balcony/Patio when booking a vacation rental in Wailea-Makena.

How many vacation homes with pools are in Wailea-Makena?

Wailea-Makena has 5,040 Condo and Apartment rental on offer to rent.

Are pets allowed in vacation homes in Wailea-Makena?

If traveling with a dog in Wailea-Makena, 3% of vacation rentals allow pets.

Top cities to visit

The most popular districts and quarters in Wailea-Makena:

Similar vacation rentals nearby

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