
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

Hawaiian Paradise Escape Across Street from Beach

Cajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01

Endless Waves, Spectacular Oceanfront views!

Sugar Beach Resort #532 - Maui HI

Tropical Resort Across Beach With Turtles!

Maui Tranquility - Relax, Unwind & Feel Welcomed!

Ocean-view Maui Condo near Beach

Beautiful Ocean Views In Maui Kamaole.
Family- and pet-friendly home rentals

Beautiful Views~

Maui Beach House

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

Pookela Paradise-Newly Renovated, Fantastic Views!

Kula Jewel - Pool, Hot Tub & Awesome Views!

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"

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

Two Bedroom Paia North Shore Beach House
Family-friendly home rentals with a pool

12 Yds to the Beach-Kihei Beach #207

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates

Luxury Wailea Beach Condo

Beautiful Ocean Views and Aloha at Wailea Ekolu!

Maui View

Gaze out at Panoramic Ocean Views from an Airy Coastal Oasis

Oceanview and amazing kitchen Palms at Wailea #503

Cute one BR ground floor. Long & short term rates
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
- Honolulu Holiday rentals
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- Waterfront rentals Wailea
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- Rentals with a washing machine and dryer Wailea
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- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Changs Beach
- Pahoa Beach
- Manele Golf Course
- Kaipukaihina
- Wailea Beach
- Hāmoa Beach
- Maui Ocean Center
- Kapua
- Oneloa Beach
- Puu Olai Beach
- Old Lahaina Luau
- Maui Golf & Sports Park
- Pōhakukāʻanapali
- Wailau Valley
- Palauea Beach
- Things to do Wailea
- Sports activities Wailea
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- Nature and outdoors Wailea
- Food and drink Wailea
- Things to do Maui County
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- Things to do Hawaii
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- Things to do United States
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- Entertainment United States
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- Sports activities United States
- Nature and outdoors United States
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- Food and drink United States