Family-Friendly Vacation Rentals in Windward Coast, USA: Compare 10+ Sites & Save

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79 Best Family Vacation Rentals in Windward Coast (Starting from $142)

@ Marbella Lane - Sunshine Seascape Ocean View
@ Marbella Lane - Sunshine Seascape Ocean View
House
Kaneohe, HI, USA
3.3k from Windward Coast center

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

4 Bedrooms8 Guests
New to Booking
$573
Average price / night
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Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Apartment
Kailua, HI, 96734, United States
2.3k from Windward Coast center

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

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$383
Average price / night
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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
4.2k from Windward Coast center

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

2 Bedrooms6 Guests
New to Booking
$261
Average price / night
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Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
House
Kailua, HI, 96734, United States
2.6k from Windward Coast center

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

4 Bedrooms8 Guests
10.0

Exceptional

89 reviews

$1720
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
4.3k from Windward Coast center

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

4 Bedrooms14 Guests
New to Booking
$1890
Average price / night
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Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
House
Kailua, HI, 96734, United States
2.8k from Windward Coast center

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

3 Bedrooms8 Guests
9.0

Fabulous

89 reviews

$372
Average price / night
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Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
House
Kailua, HI, USA
4.7k from Windward Coast center

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

3 Bedrooms7 Guests
New to Booking
$209
Average price / night
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Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

3 Bedrooms7 Guests
9.0

Fabulous

2 reviews

$373
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
4.8k from Windward Coast 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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Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

1 Bedroom4 Guests
9.8

Exceptional

76 reviews

$240
Average price / night
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Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
5.0k from Windward Coast center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
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Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

4 Bedrooms8 Guests
9.8

Exceptional

45 reviews

$426
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Windward Coast, USA
5.0k from Windward Coast 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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Hale Maluhia - Gorgeous Kaneohe Bay Home
Hale Maluhia - Gorgeous Kaneohe Bay Home
House
Kaneohe, HI, 96744, United States
3.2k from Windward Coast center

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

4 Bedrooms8 Guests
10.0

Exceptional

24 reviews

$354
Average price / night
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Kailani Loft, Kailua Coconut Grove 1-bedroom
Kailani Loft, Kailua Coconut Grove 1-bedroom
Apartment
Kailua, HI, USA
5.2k from Windward Coast 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
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KAILUA-STEPS TO THE BEACH
KAILUA-STEPS TO THE BEACH
House
Kailua Beach, HI, 96734, United States
3.3k from Windward Coast center

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

2 Bedrooms5 Guests
10.0

Exceptional

87 reviews

$182
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
5.7k from Windward Coast center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
Check Availability
Kailua Private Place in Paradise. Sleeps 2 to 4! Full Kitchen, AC, lanai w/BBQ
Kailua Private Place in Paradise. Sleeps 2 to 4! Full Kitchen, AC, lanai w/BBQ
Apartment
Kailua, HI, 96734, United States
3.4k from Windward Coast center

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

2 Bedrooms4 Guests
9.6

Exceptional

61 reviews

$142
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
5.7k from Windward Coast 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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Spacious Waterfront with Gorgeous View & Pool
Spacious Waterfront with Gorgeous View & Pool
Villa
Kaneohe, HI, 96744, United States
3.5k from Windward Coast center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$937
Average price / night
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Luxury beachfront villa on a world class beach in Kailua, HI
Luxury beachfront villa on a world class beach in Kailua, HI
House
Kailua, HI, 96734, United States
3.7k from Windward Coast center

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

6 Bedrooms18 Guests
10.0

Exceptional

2 reviews

$4253
Average price / night
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Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
House
Kailua, HI, 96734, United States
3.8k from Windward Coast center

AC, Balcony, Dryer, Free Parking, Heater, Hot Tub, Kitchen, Microwave, No Smoking

7 Bedrooms14 Guests
New to Booking
$4187
Average price / night
Check Availability
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
House
Kailua, HI, 96734, United States
3.9k from Windward Coast center

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

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$1354
Average price / night
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★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach
★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach
House
Kailua, HI, 96734, United States
3.9k from Windward Coast center

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

4 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$1084
Average price / night
Check Availability
Relaxing oceanfront home overlooking Kaneohe Bay
Relaxing oceanfront home overlooking Kaneohe Bay
House
Kaneohe, HI, 96744, United States
4.0k from Windward Coast center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$407
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
4.1k from Windward Coast 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
KAILUA BEACH VILLA - 1990/NUC-1798
KAILUA BEACH VILLA - 1990/NUC-1798
House
Kailua, HI, 96734, United States
4.2k from Windward Coast center

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

8 Bedrooms14 Guests
9.4

Superb

86 reviews

$2894
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 Windward Coast.

Where to stay in Windward Coast? Best neighborhoods & areas

Stay Near Windward Coast's Top Attractions

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

Windward Coast Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 79 verified family-friendly vacation rentals in Windward Coast. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Windward Coast vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $142 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Windward Coast 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 Windward Coast 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 Windward Coast often include amenities such as Child Friendly, Internet, and 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.