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

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343 Best Family Vacation Rentals in Wailua Homesteads (Starting from $188)

Wailua Riverside Cottage - TVNC #1293 AC Kayaks, Paddle Boards!
Wailua Riverside Cottage - TVNC #1293 AC Kayaks, Paddle Boards!
Apartment
Kapaa, USA
4.4k from Wailua Homesteads center

Air Conditioner, Parking, Internet, Child Friendly

1 Bedroom2 Guests
7.0

Good

1 reviews

$217
Average price / night
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Beautiful 3 Bed Home in the Wailua Rise Estates, TVNC 1079, 377/night for four
Beautiful 3 Bed Home in the Wailua Rise Estates, TVNC 1079, 377/night for four
House
Kapaa, HI, 96746, United States
1.5k from Wailua Homesteads center

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

3 Bedrooms6 Guests
9.8

Exceptional

119 reviews

$477
Average price / night
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Fern Grotto Inn
Fern Grotto Inn
House
Kapaa, HI, USA
4.5k from Wailua Homesteads center

Accommodations, Parking, Villas, Vacation homes, Cottages, 3-star, Lodgings, Vacation rentals, Places to stay

11 Bedrooms22 Guests
9.1

Superb

51 reviews

$298
Average price / night
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Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!
Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!
House
Kapaa, HI, 96746, United States
4.5k from Wailua Homesteads center

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

3 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$624
Average price / night
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Worldmark Kapaa Shore
Worldmark Kapaa Shore
Apartment
Kapaa, HI, USA
4.7k from Wailua Homesteads center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering

3 Bedrooms10 Guests
7.4

Good

33 reviews

$188
Average price / night
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Luxury Gated Oceanfront Condo on Ground Floor
Luxury Gated Oceanfront Condo on Ground Floor
Condo
Kauai County, HI, 96746, United States
4.8k from Wailua Homesteads center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$1040
Average price / night
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Wailua Bay View 115
Wailua Bay View 115
Apartment
Kapaa, HI, USA
4.7k from Wailua Homesteads center

Apartments, Accommodations, Pools, Lodgings, Beach, Places to stay, Family

2 Bedrooms4 Guests
8.8

Fabulous

4 reviews

$341
Average price / night
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OCEANFRONT - BREATHTAKING!  PONO KAI Condo!! 2bd2bth! Washer/Dryer/AC
OCEANFRONT - BREATHTAKING! PONO KAI Condo!! 2bd2bth! Washer/Dryer/AC
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

AC, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet

2 Bedrooms6 Guests
9.2

Superb

96 reviews

$448
Average price / night
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Luxury Oceanfront ground floor condo
Luxury Oceanfront ground floor condo
House
Kapaa, HI, USA
4.8k from Wailua Homesteads center

Luxury, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms6 Guests
New to Booking
$1339
Average price / night
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Ground floor condo in beautiful Lae Nani!
Ground floor condo in beautiful Lae Nani!
Condo
Kapaʻa, HI, 96746, United States
4.8k from Wailua Homesteads center

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

2 Bedrooms6 Guests
9.8

Exceptional

25 reviews

$494
Average price / night
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Gardenfront Escape with Ocean Views at Kapa’a Sands 24
Gardenfront Escape with Ocean Views at Kapa’a Sands 24
House
Kapaa, HI, USA
4.8k from Wailua Homesteads center

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

2 Bedrooms4 Guests
8.7

Fabulous

13 reviews

$258
Average price / night
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Hale Awa'puhi 1-C Oceanfront Luxury 2 BR w/ AC and Private Beach Access
Hale Awa'puhi 1-C Oceanfront Luxury 2 BR w/ AC and Private Beach Access
Condo
Kapaa, HI, 96746, United States
4.8k from Wailua Homesteads center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

40 reviews

$814
Average price / night
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"Sea Haven" at the Wailua Bay View 305
"Sea Haven" at the Wailua Bay View 305
Apartment
Kapaa, HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
8.0

Good

1 reviews

$304
Average price / night
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Luxury 2-Story Oceanfront Condo w/ Views & Pool
Luxury 2-Story Oceanfront Condo w/ Views & Pool
Apartment
Wailua, HI, 96746, United States
4.8k from Wailua Homesteads center

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

9.4

Superb

57 reviews

$983
Average price / night
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Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Apartment
HI, USA
4.8k from Wailua Homesteads center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Beach, Places to stay, Condos

1 Bedroom2 Guests
New to Booking
$280
Average price / night
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Oceanfront Lae Nani Beach Resort Luxury Ground Floor on  Wailua Bay
Oceanfront Lae Nani Beach Resort Luxury Ground Floor on Wailua Bay
Condo
wailua, HI, 96746, United States
4.9k from Wailua Homesteads center

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

2 Bedrooms4 Guests
9.0

Fabulous

36 reviews

$358
Average price / night
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"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
House
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom4 Guests
8.0

Good

1 reviews

$326
Average price / night
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Beachfront condo with amazing pool, grill, large lanai, & children's items
Beachfront condo with amazing pool, grill, large lanai, & children's items
Condo
Kapaa, HI, 96746, United States
4.9k from Wailua Homesteads center

Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

10 reviews

$529
Average price / night
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Charming Wailua Bay View Oceanfront Top Floor with an Amazing View!
Charming Wailua Bay View Oceanfront Top Floor with an Amazing View!
House
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
9.0

Fabulous

3 reviews

$304
Average price / night
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NEW! \"Aloha Kai\": Oceanfront at Lae Nani's Newest Renovation + AC + Free Laundry
NEW! \"Aloha Kai\": Oceanfront at Lae Nani's Newest Renovation + AC + Free Laundry
Condo
Kapaa, HI, 96746, United States
5.0k from Wailua Homesteads center

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

1 Bedroom4 Guests
10.0

Exceptional

20 reviews

$553
Average price / night
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Stunning Oceanfront View Top Floor Condo at Wailua Bay View
Stunning Oceanfront View Top Floor Condo at Wailua Bay View
House
HI, USA
4.8k from Wailua Homesteads center

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

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$326
Average price / night
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New Listing! Charming Kapa'a Garden Cottage
New Listing! Charming Kapa'a Garden Cottage
House
KAPAA, HI, 96746, United States
5.0k from Wailua Homesteads center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$370
Average price / night
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Kauai Hale Melemele Cottage 1 Block to the Beach!
Kauai Hale Melemele Cottage 1 Block to the Beach!
House
KAPAA, HI, 96746, United States
5.0k from Wailua Homesteads center

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

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$442
Average price / night
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Lae Nani #621, AC, Ocean View, Tropical Oasis, Steps to Beach and Town
Lae Nani #621, AC, Ocean View, Tropical Oasis, Steps to Beach and Town
Condo
Kapaa, HI, 96746, United States
5.0k from Wailua Homesteads center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$530
Average price / night
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The Hoover's - Lae Nani Condo #317 - Kauai, Hawaii USA
The Hoover's - Lae Nani Condo #317 - Kauai, Hawaii USA
Apartment
Kauai County, HI, 96746, United States
5.0k from Wailua Homesteads center

Barbecue, Extra Bed, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool

1 Bedroom4 Guests
10.0

Exceptional

66 reviews

$301
Average price / night
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Luxury Oceanfront Condo - Fabulous Ground Floor 3BR/2BA, Sleeps 6 - Lae Nani 511
Luxury Oceanfront Condo - Fabulous Ground Floor 3BR/2BA, Sleeps 6 - Lae Nani 511
Condo
Kapaa, HI, 96746, United States
5.0k from Wailua Homesteads center

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

3 Bedrooms6 Guests
10.0

Exceptional

115 reviews

$894
Average price / night
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Prime Beachfront location at Lae Nani ~ Best of the Best !!
Prime Beachfront location at Lae Nani ~ Best of the Best !!
Condo
Kapaa, HI, 96746, United States
5.0k from Wailua Homesteads center

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

1 Bedroom3 Guests
10.0

Exceptional

189 reviews

$473
Average price / night
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Pro Tip:
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Wailua Homesteads Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 343 verified family-friendly vacation rentals in Wailua Homesteads. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Wailua Homesteads vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $188 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Wailua Homesteads 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 Wailua Homesteads 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 Wailua Homesteads 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.