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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.
Wailea is also the sunniest, calmest base on the island and the closest to Haleakala, so the evenings and the pre-dawn sunrise drive are when parents most often want a sitter. A South Maui sitter on Tutti comes to the resort or villa; rates typically run $25-$45 per hour.
100+
Verified babysitters across Hawaii
1,200+
Families served since 2024
Families are in good hands.
- Background checkedEvery helper passes an identity and background check before their profile goes live.
- Meet on video firstFree video call with your sitter from the Tutti chat, before you book or pay.
- Free cancellationFull refund if you cancel at least 24 hours before your booking start time.
- Real human supportCall or text 808-298-0235 or email info@tuttivacation.com
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.
- South Maui sitters who know the Wailea resorts, Kihei and Makena
- Villa and suite care - naps, dinner and bedtime on your schedule
- Pre-dawn bookings for the Haleakala sunrise drive
- Background-checked, with reviews from other Wailea families
- Rate shown on every profile - $25 to $45/hour
Where families stay
Which Wailea resort suits your family?
Three Wailea resorts come up most with families, and each has its own Tutti page with resort-specific booking notes. Our full comparison is in the best Maui family resorts.
| Resort | Best for | Babysitting |
|---|---|---|
| Grand Wailea | Pools: the Wailea Canyon Activity Pool, waterslides and a water elevator | Grand Wailea babysitters |
| Four Seasons Resort Maui | Luxury with a dedicated kids club, Kids For All Seasons | Four Seasons Maui babysitters |
| Fairmont Kea Lani | All-suite space for families who want room to spread out | Fairmont Kea Lani babysitters |
South Maui with kids
What is there to do in Wailea with kids?
The Wailea beaches are among the calmest on Maui, and the beach path links most of them. A few family favorites:
- Wailea Beach - calm water for snorkeling and relaxing
- Charlie Young Beach - gentle waves and golden sand, a playground for all ages
- Polo Beach - quieter, with soft sand and gentle waves
- Keawekapu Beach - swimming and sunset views
- Big Beach (Makena) - a huge stretch of sand, but the shore break can be rough with kids
Where to go on a night out
With a sitter at the villa, these South Maui spots from our area guide are a short drive away:
- Morimoto - sushi and Japanese cuisine, a classic parents-only night
- Humble Market Kitchen - fresh, locally sourced Hawaiian flavors
- Lineage - Hawaiian comfort food with a modern twist
More beaches, Kihei and Makena are in the South Maui section of our Maui family travel guide.
Hospitality-professional · background-checked
Meet Maui babysitters serving Wailea
Trusted multitaskers across Maui, Oʻahu, and Kauaʻi - ready for your vacation.
Simple process
How to book a babysitter in Wailea
In peak seasons, booking 1-2 weeks ahead gives you the widest choice of Wailea sitters.
Browse Wailea babysitters
See which South Maui sitters cover Wailea, Kihei and Makena, then compare their experience with your children's ages, their reviews and their hourly rate.
Tell us your resort and plans
Name your Wailea resort or villa, the nights you want to go out, and whether a Haleakala sunrise run is on the list. South Maui sitters reply with their availability and rate.
Book and go
Pay on the platform and your sitter arrives at the room or villa - in time for the dinner reservation, or before you leave in the dark for Haleakala.
Real families
Stories from families visiting Maui
Across Maui, Oʻahu, and Kauaʻi resorts
★★★★★
"Mali was a wonderful babysitter for my daughter. She arrived on time, was very kind and attentive, and made sure everything went smoothly. M…"
★★★★★
"Janalise is amazing! I was nervous to book a babysitter we didn’t know while on vacation- but from our first conversation I could tell Jana…"
★★★★★
"Me-shell was wonderful with our two sets of kids ages 8,6,5,4,2.5 years old. She was very easy to coordinate the time and helpful in bringin…"
★★★★★
"Laura very helpful, and very thankful that take my request last minute! My daughter was taken care ❤️"
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. A sitter only appears on Tutti after identity verification and a background check, which matters in Wailea, where a resort concierge agency usually sends someone you have never seen. On Tutti you read reviews from other visiting families first.
How much does a babysitter cost in Wailea?
The same $25-$45 per hour as the rest of Maui - a Wailea address does not change the rate. What moves it is the number of children and how long you book, and a long Haleakala sunrise booking costs more than a dinner. Each profile shows its rate before you confirm.
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.