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

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  3.  USA

  4.  Hawaii

  5.  Kailua-Kona

  6.  Historic Kailua Village

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1116 Best Family Vacation Rentals in Historic Kailua Village (Starting from $172)

Alii Villas 307
Alii Villas 307
Apartment
Historic Kailua Village, Kailua-Kona, Hawaii, USA
0.1k from Historic Kailua Village center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family, Accessible hotels

2 Bedrooms4 Guests
8.8

Fabulous

16 reviews

$382
Average price / night
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Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool
Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool
House
Kailua-Kona, HI, 96740, United States
0.1k from Historic Kailua Village center

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

4 Bedrooms12 Guests
8.6

Fabulous

7 reviews

$1388
Average price / night
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Kona Plaza#218
Kona Plaza#218
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
New to Booking
$172
Average price / night
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Heart of Kona Ocean View Condo w/ Pool, Oversized Lanai, Incredible Location
Heart of Kona Ocean View Condo w/ Pool, Oversized Lanai, Incredible Location
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Barbecue, Crib, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen

2 Bedrooms4 Guests
9.6

Exceptional

37 reviews

$419
Average price / night
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Kona Plaza#203
Kona Plaza#203
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
6.5

Good

2 reviews

$254
Average price / night
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Peaceful Retreat • 5 min Walk to Town, Pier & Beach • Free Parking
Peaceful Retreat • 5 min Walk to Town, Pier & Beach • Free Parking
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
9.6

Exceptional

5 reviews

$253
Average price / night
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Kona Plaza#411
Kona Plaza#411
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
New to Booking
$251
Average price / night
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The Flying Honu is located in the heart of Kona Town
The Flying Honu is located in the heart of Kona Town
Apartment
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

110 reviews

$209
Average price / night
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Kona Plaza#221
Kona Plaza#221
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$261
Average price / night
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Kailua-Kona Condo w/ Lanai, Walk to Beach + Pier!
Kailua-Kona Condo w/ Lanai, Walk to Beach + Pier!
Condo
Kauila-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

1 Bedroom4 Guests
9.8

Exceptional

84 reviews

$236
Average price / night
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Kalanikai #319
Kalanikai #319
Apartment
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Apartments, Accommodations, Pools, Lodgings, Places to stay

1 Bedroom4 Guests
5.0

Review score

1 reviews

$240
Average price / night
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 Completely redecorated Aug. 2019 1 block to beach, free wi-fi, parking, and AC
Completely redecorated Aug. 2019 1 block to beach, free wi-fi, parking, and AC
Condo
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

2 Bedrooms5 Guests
9.2

Superb

98 reviews

$320
Average price / night
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Kona Plaza#302
Kona Plaza#302
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$245
Average price / night
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In Town Ocean View Condo-Walk to the Beach, Shops, Restaurants and Bars!
In Town Ocean View Condo-Walk to the Beach, Shops, Restaurants and Bars!
Condo
Kailua Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

2 Bedrooms5 Guests
9.4

Superb

101 reviews

$321
Average price / night
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Kalanikai 118 - Highly Walkable
Kalanikai 118 - Highly Walkable
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
New to Booking
$237
Average price / night
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One Bedroom, First Floor, Fully Furnished Condo
One Bedroom, First Floor, Fully Furnished Condo
Condo
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

1 Bedroom4 Guests
9.6

Exceptional

154 reviews

$188
Average price / night
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Kona Plaza#414
Kona Plaza#414
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom4 Guests
New to Booking
$294
Average price / night
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Apt A. w/ Balcony & Ocean View in Kona town -Walkable to shops, stores & beaches
Apt A. w/ Balcony & Ocean View in Kona town -Walkable to shops, stores & beaches
Apartment
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

2 Bedrooms6 Guests
7.8

Good

8 reviews

$270
Average price / night
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Kona Plaza#409
Kona Plaza#409
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

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

1 Bedroom8 Guests
New to Booking
$942
Average price / night
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Entire 3bedrooms Apt. w/ Balcony & Ocean Sunset View, Great Location
Entire 3bedrooms Apt. w/ Balcony & Ocean Sunset View, Great Location
Apartment
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

3 Bedrooms20 Guests
9.0

Fabulous

6 reviews

$513
Average price / night
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2BR-Hawaiian Style Apt. C/D in Kona town, Great Location, Walkable to everything
2BR-Hawaiian Style Apt. C/D in Kona town, Great Location, Walkable to everything
Apartment
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms6 Guests
8.0

Good

10 reviews

$265
Average price / night
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OCEAN VIEW! – 603 KAILUA VILLAGE!  NEW INTERIOR DOWNTOWN KONA - 1 BLOCK TO BAY!
OCEAN VIEW! – 603 KAILUA VILLAGE! NEW INTERIOR DOWNTOWN KONA - 1 BLOCK TO BAY!
Condo
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

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

1 Bedroom3 Guests
9.8

Exceptional

10 reviews

$258
Average price / night
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Downtown Kailua-Kona Condo w/ Pool & Views
Downtown Kailua-Kona Condo w/ Pool & Views
Condo
Kailua-Kona, HI, 96740-3118, United States
0.3k from Historic Kailua Village center

AC, Crib, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
9.6

Exceptional

23 reviews

$296
Average price / night
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Simply perfect! No one can beat 10 minutes walking to town, yet no traffic noise
Simply perfect! No one can beat 10 minutes walking to town, yet no traffic noise
House
Kailua-Kona, HI, 96740, United States
0.4k from Historic Kailua Village center

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

5 Bedrooms12 Guests
9.6

Exceptional

76 reviews

$728
Average price / night
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Kona Oceanview Penthouse in Kailua Village - Best Kona Location/View!
Kona Oceanview Penthouse in Kailua Village - Best Kona Location/View!
Condo
Kailua-Kona, HI, 96740, United States
0.4k from Historic Kailua Village center

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

3 Bedrooms6 Guests
9.8

Exceptional

98 reviews

$415
Average price / night
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Kailua Studio w/ Pool Access & Garden Views!
Kailua Studio w/ Pool Access & Garden Views!
Apartment
Kailua-Kona, HI, 96740, United States
0.4k from Historic Kailua Village center

AC, Barbecue, Free Parking, Hot Tub, Kitchen, Laundry, Microwave, No Smoking, Pool

1 Bedroom2 Guests
8.0

Good

25 reviews

$214
Average price / night
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Downtown Kona Retreat | Walk to Restaurants, Beaches & Shops
Downtown Kona Retreat | Walk to Restaurants, Beaches & Shops
Condo
Kailua-Kona, HI, 96740, United States
0.4k from Historic Kailua Village center

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

1 Bedroom2 Guests
8.6

Fabulous

14 reviews

$200
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 Historic Kailua Village.

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Historic Kailua Village Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1116 verified family-friendly vacation rentals in Historic Kailua Village. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Historic Kailua Village vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $172 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Historic Kailua Village 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 Historic Kailua Village 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 Historic Kailua Village often include amenities such as Child Friendly, Pool, 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.