Owner Direct Family Rentals in Kihei

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  5.  Kihei

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2198 Kihei Family Rentals From $249

Organizing a family trip to Kihei? Discover large vacation rentals designed with plenty of room for group dining and recreation. Owner Direct lists verified multi-bedroom properties so the whole family stays comfortable.

Beach House Getaway
Beach House Getaway
House
Kihei, HI, USA
0.6k from Kihei center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$540
Average price / night
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PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
House
Kihei, HI, 96753, United States
0.4k from Kihei center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

191 reviews

$995
Average price / night
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103 Kihei Holiday
103 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay

1 Bedroom7 Guests
9.3

Superb

3 reviews

$469
Average price / night
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2BD/2BA! Charming Retreat: Ground Floor w/King, AC, Garden/Lanai
2BD/2BA! Charming Retreat: Ground Floor w/King, AC, Garden/Lanai
Condo
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$391
Average price / night
Check Availability
110 Kihei Holiday
110 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom7 Guests
1.0

Review score

1 reviews

$469
Average price / night
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☼ Stylish & Bright 2bd Oceanfront Condo|5★ Views
☼ Stylish & Bright 2bd Oceanfront Condo|5★ Views
Condo
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

11 reviews

$409
Average price / night
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214 Kihei Holiday
214 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom7 Guests
9.3

Superb

3 reviews

$491
Average price / night
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Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
House
Kihei, HI, 96753, United States
0.5k from Kihei center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Internet

6 Bedrooms18 Guests
10.0

Exceptional

46 reviews

$3469
Average price / night
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Kihei Holiday 311
Kihei Holiday 311
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Cheap, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms7 Guests
8.3

Very Good

9 reviews

$434
Average price / night
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Kihei - Tropical Cottage Across from the Beach - PERMIT # STKM 2015/0003
Kihei - Tropical Cottage Across from the Beach - PERMIT # STKM 2015/0003
Cottage
Kihei, HI, 96753-7716, United States
0.6k from Kihei center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

55 reviews

$667
Average price / night
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107 Kihei Holiday
107 Kihei Holiday
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$249
Average price / night
Check Availability
Steps to Sugar Beach!
Steps to Sugar Beach!
Condo
Kihei, HI, 96753, United States
0.7k from Kihei center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$451
Average price / night
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Your Maui Adventure Awaits - Sugar Beach
Your Maui Adventure Awaits - Sugar Beach
Apartment
Kihei, HI, USA
0.7k from Kihei center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Condos

2 Bedrooms5 Guests
New to Booking
$336
Average price / night
Check Availability
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
House
Kihei, HI, 96753, United States
0.7k from Kihei center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

6 Bedrooms17 Guests
9.6

Exceptional

220 reviews

$2531
Average price / night
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Nona Lani Cottages
Nona Lani Cottages
Apartment
Kihei, Hawaii, USA
0.7k from Kihei center

Apartments, Accommodations, Parking, 4-star, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

11 Bedrooms10 Guests
9.3

Superb

106 reviews

$446
Average price / night
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Ocean-View Kihei Condo w/ Pool Access!
Ocean-View Kihei Condo w/ Pool Access!
Condo
Kihei, HI, 96753, United States
0.7k from Kihei center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Kitchen

2 Bedrooms4 Guests
9.2

Superb

91 reviews

$372
Average price / night
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Newly Remodeled Steps to Sugar Beach!
Newly Remodeled Steps to Sugar Beach!
Condo
Kihei, HI, 96753, United States
0.7k from Kihei center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms7 Guests
8.8

Fabulous

15 reviews

$524
Average price / night
Check Availability
Best 2BR Oceanview on property! Modern, luxury unit. Whales, Beach, Pool, AC!
Best 2BR Oceanview on property! Modern, luxury unit. Whales, Beach, Pool, AC!
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

18 reviews

$466
Average price / night
Check Availability
Newly Remodeled Boutique Beachside 2bd | Aloha Pualani Suite 1
Newly Remodeled Boutique Beachside 2bd | Aloha Pualani Suite 1
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave

2 Bedrooms7 Guests
New to Booking
$466
Average price / night
Check Availability
2BR Oceanview Family Favorite! Beach, Pool, Hot Tub, AC! Whale Season Views!
2BR Oceanview Family Favorite! Beach, Pool, Hot Tub, AC! Whale Season Views!
Condo
Kihei, HI, 96753, United States
0.8k from Kihei center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.6

Exceptional

87 reviews

$397
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Friendly Rentals in Kihei.

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Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Kihei. If you plan on staying in the Kihei area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Kihei

You can explore 2198 verified family-friendly vacation rentals in Kihei. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Kihei vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $249 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Kihei offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it's helpful to check the listing details before booking.

Yes, some rentals in Kihei are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Kihei often include amenities such as Child Friendly, Wellness Facilities, and Laundry. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.