
Family-friendly holiday rentals in Wailea
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wailea
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea family-friendly rentals
Family-friendly home rentals with a hot tub

Maui Condo Steps From Beach & Ocean (Hotel Zoned)

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Partial OCEAN View! 2 Bedroom w/ AC, Pool & BBQ!

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Renovated Condo | 3 Min Walk to Toes in the Sand!

☀Very Desirable South Kihei | Enlivening Getaway ☀

Grand Champions 169 Beautiful 3 BR on the Fairway!

Beautiful Palms At Wailea #608-July/Aug. Discount
Family- and pet-friendly home rentals

Mana Hale Vacation Rental

Maui Meadows Ocean View Cottage

Oceanside Ohana & Banana Bread Near Beach-OGG-MACC

High-Floor Island Surf | AC | Walk to Beach

Resort Studio w/ 2 Beds-Walk to Beach Shops Dining

Mermaid Bungalow

2B/2B Cottage/Cozy/Central/Private/Historic town

Oceanfront renovated luxury-best location! SBR 404
Family-friendly home rentals with a pool

Upscale and Elegant Vistas

Prime Location, in the HEART of it ALL!

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

Wailea Ocean View Escape

Maui Retreat Ekahi 50F -All YOU Need!

Ekahi 22C Toes in the Sand in Under 2 Minutes

Modern Renovated Palms at Wailea Condo!

Wailea Elua Village | 1504
Quick stats about holiday rentals that are family-friendly in Wailea
Total rentals
1K properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
26K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
990 properties have a pool
Rentals with dedicated workspaces
570 properties have a dedicated workspace
Destinations to explore
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Serviced apartment rentals Wailea
- Rentals with an EV charger Wailea
- Cottage rentals Wailea
- Beach condo rentals Wailea
- Pet-friendly rentals Wailea
- Waterfront rentals Wailea
- Rentals with a sauna Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Fitness-friendly rentals Wailea
- Apartment rentals Wailea
- Hotel rentals Wailea
- Rentals with a washing machine and dryer Wailea
- Rentals with pools Wailea
- Condo rentals Wailea
- Villa rentals Wailea
- Luxury rentals Wailea
- House rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Family-friendly rentals Wailea
- Family-friendly rentals Maui County
- Family-friendly rentals Hawaii
- Family-friendly rentals United States
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Olowalu Beach
- Manele Golf Course
- Hāmoa Beach
- Kaipukaihina
- Maui Ocean Center
- Wailea Beach
- Kapua
- Puu Olai Beach
- Changs Beach
- Oneloa Beach
- Maui Golf & Sports Park
- Old Lahaina Luau
- Palauea Beach
- Ka'anapali Golf Courses
- Wailau Valley
- Wailea Golf Club
- Mokulau Beach
- Paukukalo Beach