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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Hawaii

  5.  Kailua

Refine your search

Price per night

Amenity Filter

Rating

87 Best Family Vacation Rentals in Kailua (Starting from $138)

Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Kailua, Hawaii, USA
0.2k from Kailua 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
Check Availability
Kakela Kai, Beachfront Kailua Home, Private, A/C
Kakela Kai, Beachfront Kailua Home, Private, A/C
House
Kailua, HI, 96734, United States
0.1k from Kailua center

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

4 Bedrooms10 Guests
10.0

Exceptional

14 reviews

$1099
Average price / night
Check Availability
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
0.4k from Kailua center

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

5 Bedrooms10 Guests
New to Booking
$2342
Average price / night
Check Availability
Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi
Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi
House
Kailua, HI, 96734, United States
0.2k from Kailua center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms6 Guests
New to Booking
$480
Average price / night
Check Availability
Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
0.8k from Kailua center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
Check Availability
'Star of Hawaii'  Beachside, Pool, Steps to Beach - Great for Families
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
House
Kailua, HI, 96734, United States
0.2k from Kailua center

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

4 Bedrooms10 Guests
9.4

Superb

98 reviews

$669
Average price / night
Check Availability
Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
0.9k from Kailua center

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

4 Bedrooms14 Guests
New to Booking
$1890
Average price / night
Check Availability
 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
0.4k from Kailua center

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

4 Bedrooms8 Guests
10.0

Exceptional

47 reviews

$1466
Average price / night
Check Availability
Beachfront spectacular Kailua beach
Beachfront spectacular Kailua beach
House
Kailua, Hawaii, USA
0.9k from Kailua center

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

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1224
Average price / night
Check Availability
Happy House on Exquisite Kailua Beachside Property!
Happy House on Exquisite Kailua Beachside Property!
House
Kailua, HI, 96734, United States
0.4k from Kailua center

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

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$583
Average price / night
Check Availability
Kailani Loft, Kailua Coconut Grove 1-bedroom
Kailani Loft, Kailua Coconut Grove 1-bedroom
Apartment
Kailua, HI, USA
0.9k from Kailua center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom3 Guests
9.3

Superb

47 reviews

$193
Average price / night
Check Availability
Available and legal for stays less than 30 days.
Available and legal for stays less than 30 days.
Apartment
Kailua, HI, 96734, United States
0.5k from Kailua 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
Check Availability
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
0.9k from Kailua center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
Check Availability
Entire Fantastic Kailua Cottage.. waiting for you!
Entire Fantastic Kailua Cottage.. waiting for you!
Apartment
Kailua, HI, 96734, United States
0.5k from Kailua center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill

10.0

Exceptional

17 reviews

$143
Average price / night
Check Availability
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
0.9k from Kailua center

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

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
Check Availability
Beautiful Beachside Bungalow
Beautiful Beachside Bungalow
Cottage
Kailua, HI, 96734, United States
0.5k from Kailua center

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

1 Bedroom2 Guests
10.0

Exceptional

15 reviews

$366
Average price / night
Check Availability
Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Apartment
Kailua, HI, USA
1.0k from Kailua center

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

2 Bedrooms6 Guests
New to Booking
$261
Average price / night
Check Availability
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Villa
Kailua, HI, 96734, United States
0.6k from Kailua center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

5 Bedrooms12 Guests
New to Booking
$561
Average price / night
Check Availability
Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
House
Kailua, HI, USA
1.2k from Kailua center

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

3 Bedrooms7 Guests
New to Booking
$209
Average price / night
Check Availability
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
House
Kailua, HI, 96734, United States
0.7k from Kailua center

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

6 Bedrooms16 Guests
9.8

Exceptional

76 reviews

$4216
Average price / night
Check Availability
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA
House
Kailua, HI, 96734, United States
0.7k from Kailua center

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

6 Bedrooms14 Guests
9.8

Exceptional

51 reviews

$3472
Average price / night
Check Availability
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 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
Check Availability
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
House
Kailua, HI, 96734, United States
0.8k from Kailua center

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

3 Bedrooms6 Guests
9.2

Superb

146 reviews

$899
Average price / night
Check Availability
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach
Apartment
Kailua, HI, 96734, United States
0.9k from Kailua center

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

1 Bedroom4 Guests
9.8

Exceptional

9 reviews

$171
Average price / night
Check Availability
The Perfect Escape
The Perfect Escape
Apartment
Kailua, HI, 96734, United States
1.0k from Kailua center

Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$138
Average price / night
Check Availability
Steps to Kailua Beach • Relaxing 3BR Oasis • Fenced Yard
Steps to Kailua Beach • Relaxing 3BR Oasis • Fenced Yard
House
Kailua, HI, 96734, United States
1.0k from Kailua center

Crib, Dryer, Free Parking, Internet, Laundry, Living Area, Microwave, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$326
Average price / night
Check Availability
Huge House, Heated Pool, AC, Steps to Kailua Beach
Huge House, Heated Pool, AC, Steps to Kailua Beach
House
Kailua, HI, 96734, United States
1.0k from Kailua center

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

8 Bedrooms20 Guests
9.6

Exceptional

80 reviews

$1380
Average price / night
Check Availability

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.

Where to stay in Kailua? Best neighborhoods & areas

Stay Near Kailua's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Kailua Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 87 verified family-friendly vacation rentals in Kailua. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Kailua vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $138 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Kailua 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 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 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.