Family-friendly holiday rentals in Wailea-Makena
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Top-rated family-friendly rentals in Wailea-Makena
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-Makena family-friendly rentals
Family-friendly home rentals with a hot tub
Condo in Kihei
4.89 out of 5 average rating, 139 reviewsMaui Banyan 1BR With View Across from Beach
20–27 Aug
Condo in Kihei
4.83 out of 5 average rating, 140 reviewsPalms At Wailea #608-May/June Special
24–31 Oct
Condo in Wailea
4.95 out of 5 average rating, 137 reviews4/21-5/30 Fabulous Peaceful 2bd in Upscale Wailea
15–22 Feb
Condo in Wailea-Makena
4.85 out of 5 average rating, 179 reviewsRomantic One BR Condo (Remodeled)
18–25 Apr
Townhouse in Kihei
4.79 out of 5 average rating, 284 reviewsKihei Bay Surf #149 / HI Taxes included in price
29 Jul – 5 Aug
Apartment in Kihei
4.94 out of 5 average rating, 109 reviewsKamaole Sands 7-207-Stunning Remodel-Large Lanai
27 Mar – 3 Apr
Apartment in Kihei
4.89 out of 5 average rating, 109 reviewsSugar Beach Resort #532 - Maui HI
7–14 Aug
Condo in Kihei
4.98 out of 5 average rating, 113 reviewsMaui-Time! at Maui Sunset - 2 Q beds/2 full baths
1–8 Aug
Family- and pet-friendly home rentals
Farm stay in Makawao
4.98 out of 5 average rating, 247 reviewsOcean View - Private Cabin
1–8 Aug
Apartment in Kaunakakai
4.8 out of 5 average rating, 400 reviews(Adventure or just relax) located at Hotel Molokai
27 Apr – 4 May
Home in Haiku-Pauwela
4.9 out of 5 average rating, 176 reviewsSpacious Private 3 BR Home: A/C, WiFi & CBL
1–8 Mar
Guesthouse in Wailuku
4.87 out of 5 average rating, 218 reviews2B/2Bcottage/central/private/ historic town/wi-fi
28 Nov – 5 Dec
Home in Paia
4.85 out of 5 average rating, 104 reviewsTwo Bedroom Green Turtle House Paia/North Shore
26 Jun – 3 Jul
Home in Wailea-Makena
5.0 out of 5 average rating, 66 reviewsWOW! Stunning Ocean Views, Large Deck &Luxury Beds
23–30 Aug
Home in Lanai City
4.95 out of 5 average rating, 84 reviewsThe Artists House
12–19 Sep
Condo in Lahaina
4.88 out of 5 average rating, 121 reviewsBeautiful Views~
26 Jan – 2 Feb
Family-friendly home rentals with a pool
Condo in Wailea-Makena
4.88 out of 5 average rating, 169 reviewsOcean View Wailea Ekolu Condo #804
4–11 Mar
Condo in Kihei
4.93 out of 5 average rating, 207 reviewsMagnificent remodel with ocean View
2–9 Apr
Condo in Kihei
4.93 out of 5 average rating, 218 reviewsHale Kai O Kihei 307 | Direct Beachfront
17–24 Mar
Condo in Kihei
4.81 out of 5 average rating, 202 reviewsBeautiful Condo with Ocean view!
15–22 Jul
Condo in Kihei
4.91 out of 5 average rating, 123 reviewsOcean View Condo in Kihei
17–24 Apr
Condo in Wailuku
4.99 out of 5 average rating, 156 reviewsBeautiful Oceanfront Condo- Great View, A/C,Wi-Fi
15–22 Oct
Apartment in Kihei
4.9 out of 5 average rating, 212 reviewsCozy Central Kihei Condo
11–18 Sep
Condo in Wailuku
4.91 out of 5 average rating, 103 reviewsLuxury Beachfront Condo with Amazing Ocean Views
5–12 Oct
Quick stats about holiday rentals that are family-friendly in Wailea-Makena
Total rentals
1.1K properties
Wi-Fi availability
1.1K properties include access to Wi-Fi
Rentals with dedicated workspaces
550 properties have a dedicated workspace
Rentals with a pool
1K properties have a pool
Pet-friendly rentals
10 properties allow pets
Total number of reviews
21K reviews
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