Family-Friendly Vacation Rentals in Kailua Beach, HI: Compare 10+ Sites & Save

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  6.  Kailua Beach

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90 Best Family Vacation Rentals in Kailua Beach (Starting from $173)

Beachfront spectacular Kailua beach
Beachfront spectacular Kailua beach
House
Kailua Beach, Kailua, Hawaii, USA
0.6k from Kailua Beach center

Breakfast, Internet, Private Beach, Balcony/Terrace, View, Kitchen, Air Conditioner

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1224
Average price / night
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Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
House
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

2 Bedrooms5 Guests
9.6

Exceptional

218 reviews

$646
Average price / night
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Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
1.0k from Kailua Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$936
Average price / night
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Apartment
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

1 Bedroom3 Guests
9.6

Exceptional

149 reviews

$373
Average price / night
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A Place of Peace Where Heaven Meets the Ocean
A Place of Peace Where Heaven Meets the Ocean
House
Kailua, HI, USA
1.5k from Kailua Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms4 Guests
New to Booking
$662
Average price / night
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Kailua Beach \"The Pink House\"  100 Yards from Ocean
Kailua Beach \"The Pink House\" 100 Yards from Ocean
House
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

4 Bedrooms6 Guests
10.0

Exceptional

79 reviews

$765
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Kailua Beach, Kailua, Hawaii, USA
1.7k from Kailua Beach center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
9.1

Superb

73 reviews

$275
Average price / night
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Luxury Beach Cottage in charming Kailua
Luxury Beach Cottage in charming Kailua
Cottage
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Laundry, Living Area

1 Bedroom6 Guests
New to Booking
$284
Average price / night
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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
House
Kailua, HI, USA
1.7k from Kailua Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$2342
Average price / night
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Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
10.0

Exceptional

115 reviews

$678
Average price / night
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Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Apartment
Kailua, HI, USA
1.8k from Kailua Beach center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
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Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$774
Average price / night
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Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
1.8k from Kailua Beach center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
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Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

1 Bedroom4 Guests
New to Booking
$293
Average price / night
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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
1.9k from Kailua Beach center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$976
Average price / night
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MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach!
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach!
House
Kailua, HI, 96734, United States
0.5k from Kailua Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

72 reviews

$476
Average price / night
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Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Apartment
Kailua, HI, USA
2.1k from Kailua Beach center

Apartments, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$219
Average price / night
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Tradewind Bungalow, in Kailua on Oahu
Tradewind Bungalow, in Kailua on Oahu
House
Kailua, HI, 96734, United States
0.7k from Kailua Beach center

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

2 Bedrooms6 Guests
9.8

Exceptional

145 reviews

$186
Average price / night
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Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
2.3k from Kailua Beach center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
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Wow!   Home just steps from the Beach with Private Salt Water Pool
Wow! Home just steps from the Beach with Private Salt Water Pool
House
Kailua, HI, 96734, United States
0.8k from Kailua Beach center

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

5 Bedrooms10 Guests
9.6

Exceptional

43 reviews

$1281
Average price / night
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BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
House
Kailua, HI, 96734, United States
0.8k from Kailua Beach center

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

3 Bedrooms7 Guests
10.0

Exceptional

62 reviews

$1339
Average price / night
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Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA
House
Kailua, HI, 96734, United States
0.8k from Kailua Beach center

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

6 Bedrooms14 Guests
9.8

Exceptional

51 reviews

$3472
Average price / night
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Kailua Town & Kailua Beach
Kailua Town & Kailua Beach
House
Kailua, HI, 96734, United States
0.9k from Kailua Beach center

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

3 Bedrooms6 Guests
9.6

Exceptional

53 reviews

$312
Average price / night
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Available and legal for stays less than 30 days.
Available and legal for stays less than 30 days.
Apartment
Kailua, HI, 96734, United States
1.1k from Kailua Beach center

AC, Barbecue, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

112 reviews

$344
Average price / night
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Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
House
Kailua, HI, 96734, United States
1.1k from Kailua Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

76 reviews

$647
Average price / night
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 Celebrate America's 250th Birthday &  Kailua Fireworks from  Beachfront Lanai
Celebrate America's 250th Birthday & Kailua Fireworks from Beachfront Lanai
House
Kailua, HI, 96734, United States
1.2k from Kailua Beach center

Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

47 reviews

$1466
Average price / night
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Beautiful Beachside Bungalow
Beautiful Beachside Bungalow
Cottage
Kailua, HI, 96734, United States
1.2k from Kailua Beach center

AC, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

1 Bedroom2 Guests
10.0

Exceptional

15 reviews

$366
Average price / night
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Pro Tip:
VacationByOwnerRentals 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 Vacation Rentals in Kailua Beach.

Where to stay in Kailua Beach? Best neighborhoods & areas

Kailua Beach Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 90 verified family-friendly vacation rentals in Kailua Beach. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Kailua Beach vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $173 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Kailua Beach 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 Kailua Beach 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 Kailua Beach often include amenities such as Child Friendly, View, and Ocean View. 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.