Vacation rentals in Wailea - Casamundo base64Hash Vacation rentals in Wailea - Casamundo

Vacation rentals in Wailea

Anytime
Guests
Anytime
Guests
1,035 accommodations available

  • Price per night

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

  • Rating

    • 4.5+
    • 4+

  • Popular amenities

    • Pool
    • WiFi
    • Air conditioning
    • Balcony/patio
    • Kitchen
    • Parking
    • Washing machine
    • TV
    • Dishwasher
    • Microwave
    • Hot tub
    • Garden
    • Sauna
    • Fireplace
    • Cot

  • Other Services

    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Wailea

Discover your ideal Wailea vacation rental with real-time comparisons of 1,035 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 the full description before booking.
Condo Wailea
97 m² condo ∙ 4 guests ∙ 2 bedrooms

Condo with BBQ & pool | Beach view

Wailea, Wailea-Makena, Hawaii, United States
This stunning Wailea condo offers breathtaking sea views, easy beach access, and family-friendly amenities like a pool and kitchen, making it perfect for events. Book you...
from €247
per night
Outstanding(13 ratings)
from €247
per night
Check prices
Condo Wailea
95 m² condo ∙ 4 guests ∙ 1 bedroom

Family-oriented condo with garden, BBQ & pool | Garden view

Wailea, Wailea-Makena, Hawaii, United States
This delightful Wailea condo offers beach access and fantastic amenities like a pool, hot tub, spa, and kitchen, perfect for families. Enjoy your stay with parking and a ...
from €214
per night
Outstanding(11 ratings)
from €214
per night
Check prices
Condo Wailea
130 m² condo ∙ 8 guests ∙ 3 bedrooms

Flat with pool, hot tub & barbeque | Water view

Wailea, Wailea-Makena, Hawaii, United States
This spacious 3-bedroom Wailea condo accommodates up to 8 guests and features a beautiful sea view, pool, hot tub, and beach access, making it perfect for family gatherin...
from €468
per night
Outstanding(122 ratings)
from €468
per night
Check prices
Condo Wailea
83 m² condo ∙ 4 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
This stunning Wailea condo accommodates four guests and features a beautiful sea view, a fully equipped kitchen, a family-friendly vibe, and access to a pool and beach—pe...
from €254
per night
Outstanding(115 ratings)
from €254
per night
Check prices
Condo Wailea
87 m² condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool

Wailea, Wailea-Makena, Hawaii, United States
This inviting Wailea condo accommodates up to 6 guests and features a beautiful balcony, a kitchen, and pool access. Enjoy family-friendly amenities and easy beach access...
from €261
per night
Outstanding(3 ratings)
from €261
per night
Check prices
Condo Wailea
Condo ∙ 4 guests ∙ 2 bedrooms

Flat with heated pool & BBQ | Beach view

Wailea, Wailea-Makena, Hawaii, United States
Experience a stunning waterfront condo in Wailea, featuring a heated pool, spa, and breathtaking sea and mountain views. Perfect for families, this spacious retreat offer...
from €376
per night
Excellent(5 ratings)
from €376
per night
Check prices
House Wailea
130 m² house ∙ 8 guests ∙ 3 bedrooms

House with barbecue, pool & terrace | Water view | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This spacious house rental in Wailea offers a pool, hot tub, and stunning sea views. Perfect for families, it features a kitchen, yard, balcony, and easy beach access for...
from €462
per night
Excellent(1 rating)
from €462
per night
Check prices
Condo Wailea
111 m² condo ∙ 6 guests ∙ 2 bedrooms

Condo with garden, barbecue & terrace | Garden view

Wailea, Wailea-Makena, Hawaii, United States
This stunning Wailea-Makena condo accommodates up to 6 guests and features a pool, hot tub, and beach access, along with a kitchen, balcony, and breathtaking sea views. P...
from €325
per night
Excellent(6 ratings)
from €325
per night
Check prices
House Wailea
251 m² house ∙ 10 guests ∙ 4 bedrooms

Holiday home with garden, barbecue & terrace | Suitable for remote work

Wailea, Wailea-Makena, Hawaii, United States
This stunning Wailea house rental offers a perfect getaway for up to 10 guests, featuring a pool, hot tub, fully equipped kitchen, spacious yard, and easy beach access fo...
from €1,121
per night
Outstanding(108 ratings)
from €1,121
per night
Check prices
Condo Wailea
97 m² condo ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant flat with pool & BBQ | Sea view | Beach nearby

Wailea, Wailea-Makena, Hawaii, United States
This stunning Wailea condo offers ocean views, a private balcony, and easy beach access. Enjoy a refreshing pool, a fully equipped kitchen, and convenient parking for an ...
from €329
per night
Outstanding(69 ratings)
from €329
per night
Check prices
Condo Wailea
103 m² condo ∙ 8 guests ∙ 3 bedrooms

Condo with barbeque & pool | Beach view

Wailea, Wailea-Makena, Hawaii, United States
This spacious condo in Wailea accommodates up to 8 guests and features a fully equipped kitchen, sea view balcony, pool access, and beach access, perfect for family event...
from €294
per night
Excellent(23 ratings)
from €294
per night
Check prices
Condo Wailea
72 m² condo ∙ 6 guests ∙ 2 bedrooms

Children-friendly flat with BBQ & pool | Water view | Next to the beach

Wailea, Wailea-Makena, Hawaii, United States
This stunning Kihei condo offers a perfect getaway for families, featuring a pool, beach access, and breathtaking sea views. Enjoy your own kitchen, balcony, and ample pa...
from €236
per night
Outstanding(2 ratings)
from €236
per night
Check prices
Condo Wailea
83 m² condo ∙ 6 guests ∙ 2 bedrooms

Condo with BBQ & pool | Beach view

Wailea, Wailea-Makena, Hawaii, United States
This inviting Wailea condo accommodates up to 6 guests and features a stunning sea view, a fully-equipped kitchen, a pool, beach access, and a spacious balcony, perfect f...
from €286
per night
Excellent(73 ratings)
from €286
per night
Check prices
Condo Wailea
102 m² condo ∙ 6 guests ∙ 2 bedrooms

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

Wailea, Wailea-Makena, Hawaii, United States
A stunning Wailea condo awaits, featuring beach access, a pool, and a full kitchen, perfect for families and events. Enjoy comfortable accommodations for up to 6 guests!
from €218
per night
Excellent(8 ratings)
from €218
per night
Check prices
Condo Wailea
Condo ∙ 4 guests ∙ 1 bedroom

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

Wailea, Wailea-Makena, Hawaii, United States
A stunning Kihei condo awaits, offering beach access, breathtaking sea views, and fantastic amenities including a pool, spa, and hot tub. Perfect for families or events, ...
from €192
per night
Outstanding(98 ratings)
from €192
per night
Check prices

Vacation Homes with Pools

Make a splash: Check out these Wailea vacation rentals refreshing pools!

We use AI to generate the short summary in each offer below – check the full description before booking.
Condo Wailea
from €301 per night
83 m² Condo ∙ 4 guests ∙ 2 bedrooms

Condo with terrace, barbeque & fast internet | Water view

4.8
Outstanding(17 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Pool
Check prices
Condo Wailea
from €439 per night
111 m² Condo ∙ 8 guests ∙ 2 bedrooms

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

4.8
Outstanding(24 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Pool
Check prices
Condo Wailea
from €304 per night
111 m² Condo ∙ 6 guests ∙ 2 bedrooms

Flat with barbecue, pool & jacuzzi

4.8
Outstanding(23 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Pool
Check prices
Show more offers

Vacation rentals and apartments with air conditioning

Cool comfort in Wailea: Choose a vacation rental with air conditioning - book your stay!

We use AI to generate the short summary in each offer below – check the full description before booking.
Condo Wailea
from €913 per night
127 m² Condo ∙ 4 guests ∙ 2 bedrooms

Family-friendly big condo with fast internet, hot tub & terrace | Water view | Close to the beach

4.9
Outstanding(26 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Check prices
Condo Wailea
from €249 per night
81 m² Condo ∙ 4 guests ∙ 1 bedroom

Child-friendly flat with private pool, garden & fast internet | Water view

4.5
Excellent(3 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Check prices
Condo Wailea
from €405 per night
121 m² Condo ∙ 6 guests ∙ 3 bedrooms

Family-oriented spacious condo with pool, barbeque & jacuzzi | Water view | Suitable for remote work

4.8
Outstanding(73 ratings)
Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
Check prices
See all offers
11 reviews
11 travelers who stayed in Wailea gave their vacation rental an average rating of 4.7/5 stars.

Frequently asked questions

What are the most popular accommodations in the area?

The most popular accommodation types in Wailea are condo and apartment rental. With 1,035 accommodations in Wailea, the perfect vacation home is only one click away.

How much does it cost to stay the night?

Prices start at just €192 per night. Most apartment rental in Wailea are 124 m² and condo are 92 m².

Do you offer accommodations for traveling with a group?

Yes, we definitely have accommodations for groups in Wailea. On average, the condo has space for 5 guests.

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