Kendali S
$35/hr
Verified
★★★★★Loved by families
I’m a certified Nanny trained in First Aid/CPR/AED
Vacation Babysitting · Wailea, Maui
Babysitters in Wailea
for Your Resort Stay
Wailea babysitters on Tutti Vacation are background-checked local sitters who come to your room, suite, or villa across the Wailea resorts in South Maui, so families can book trusted in-room childcare for dinners out, early sunrise trips, and spa afternoons.
Wailea is the resort spine of South Maui: the Grand Wailea, the Four Seasons, the Fairmont Kea Lani, the Andaz and the Wailea Beach Resort sit almost shoulder to shoulder along a mile and a half of beach path, with villas and condos behind them. It is the kind of place families book for a full week, which is exactly when a few child-free hours start to matter.
Tutti connects you with a South Maui sitter who meets you at your resort. Every sitter completes identity verification and a background check before their listing goes live. Rates typically run $25-$45 per hour, and more than 1,200 families have booked care through Tutti since 2024.
100+
Verified babysitters across Hawaii
1,200+
Families served since 2024
Why families choose Tutti
How do I book a babysitter at a Wailea resort?
Most Wailea properties will refer you to an agency through the concierge, which adds a booking fee and usually means you meet your sitter for the first time at the door, with no profile and no reviews beforehand. Tutti works the other way: you see who is available, what they charge, and what other families said, then book directly.
Wailea also skews toward longer stays and villa rentals, where a resort kids club is either far away or not a fit at all. A private sitter who comes to the villa handles naps, dinner, and bedtime on your schedule rather than the programme's. See all Maui babysitters.
- Verified and background-checked babysitters
- In-room and in-villa care across the Wailea resorts
- Built for dinners out, Haleakala sunrise trips, and spa afternoons
- Transparent pricing - $25 to $45/hour, no hidden fees
- Most inquiries confirmed within 15-30 minutes
Hospitality-professional · background-checked
Meet Maui babysitters serving Wailea
Trusted multitaskers across Maui, Oʻahu, and Kauaʻi - ready for your vacation.
Amy S
$30/hr
Verified
★★★★★Loved by families
I love working with kids!
Mika G
$37/hr
Verified
★★★★★Loved by families
Friendly, reliable, and active helper offering babysitti
Julieta T
$38/hr
Verified
★★★★★Loved by families
Babysitter offering Henna Tattoo add on
Kendali S
$35/hr
Verified
★★★★★Loved by families
I’m a certified Nanny trained in First Aid/CPR/AED
Amy S
$30/hr
Verified
★★★★★Loved by families
I love working with kids!
Mika G
$37/hr
Verified
★★★★★Loved by families
Friendly, reliable, and active helper offering babysitti
Julieta T
$38/hr
Verified
★★★★★Loved by families
Babysitter offering Henna Tattoo add on
Simple process
How to book a babysitter in Wailea
Most families are matched and confirmed within 15 minutes of sending their inquiry.
Browse Wailea babysitters
Explore verified South Maui sitters who serve the Wailea resorts. Compare profiles, experience with your age group, and hourly rates before you reach out.
Send your inquiry
Tell us your resort, your dates, and the ages of your children. Available Maui sitters respond within minutes with their availability and rate.
Book and go
Confirm securely on the platform. Your sitter meets you at your resort, so you can take the dinner reservation, the sunrise Haleakala drive, or the spa afternoon.
Family travel resources
Helpful Maui guides for families
These guides cover where to stay, what to do, and how to plan a South Maui trip around children's routines.
Got questions
Everything you need to know
Which Wailea resorts do Tutti babysitters serve?
Sitters cover the whole Wailea resort area, including the Grand Wailea, the Four Seasons Resort Maui, the Fairmont Kea Lani, the Andaz Maui, and the Wailea Beach Resort, plus the villa and condo complexes along Wailea Alanui Drive and neighbouring Makena. We also have dedicated pages for the Grand Wailea, the Four Seasons, and the Fairmont Kea Lani.
Do sitters come to the room or the villa?
Your sitter comes to you, whether that is a hotel room, a suite, or a private villa. Many Wailea bookings are villa stays where a kids club is not practical, and in-room care is the point.
Are Wailea babysitters background checked?
Yes. Every sitter on Tutti Vacation completes identity verification and a background check before their listing goes live, and you can read reviews from other traveling families before you book.
How much does a babysitter cost in Wailea?
Rates typically run $25-$45 per hour depending on the sitter's experience, the number of children, and the length of the booking. Every profile shows its rate before you confirm, with no resort concierge markup.
Can I book a sitter for an early Haleakala sunrise trip?
Yes. Haleakala sunrise trips leave Wailea in the middle of the night, which is one of the most common reasons families book a sitter here. An overnight or very early booking means the adults can go without waking the children at 2am.
Can we book multiple days across our stay?
Yes, and it is common in Wailea, where families often stay a week or more. You can book the same sitter for several sessions so your children see a familiar face, subject to that sitter having the dates free.
Book today
Keep the dinner reservation
while we handle the kids.
Whether you are at the Grand Wailea, the Four Seasons, the Fairmont Kea Lani, the Andaz, or a villa along the beach path, book a trusted Wailea babysitter for your evening out, sunrise drive, or spa afternoon. Verified sitters, transparent pricing, no agency hassle.