Owner Direct Vacation Rentals in Kailua Pier

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  5.  Kailua-Kona

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1509 Kailua Pier Vacation Homes From $172

Looking for the ideal vacation rental in Kailua Pier? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Big Island Kona Plaza 311 condo
Big Island Kona Plaza 311 condo
Apartment
Kailua-Kona, HI, USA
0.3k from Kailua Pier center

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

2 Bedrooms4 Guests
9.0

Fabulous

1 reviews

$174
Average price / night
Check Availability
2-bedroom Condo in Kona - Walk to Beaches, Shops & Restaurants - Booking Fast
2-bedroom Condo in Kona - Walk to Beaches, Shops & Restaurants - Booking Fast
Apartment
Kailua Kona, HI, 96740, United States
0.2k from Kailua Pier center

AC, Dryer, Internet, Laundry, No Smoking, Washer

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$457
Average price / night
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Kona Plaza#218
Kona Plaza#218
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier 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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Two Private hosted Oceanfront Homes conveniently located in Kailua Kona, Hawaii
Two Private hosted Oceanfront Homes conveniently located in Kailua Kona, Hawaii
House
Kailua Kona, HI, 96740, United States
0.2k from Kailua Pier center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Internet

13 Bedrooms34 Guests
10.0

Exceptional

2 reviews

$8006
Average price / night
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Kona Plaza#203
Kona Plaza#203
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier 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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Enjoy staying right on Keiki beach. Walking distance to the Ironman start!
Enjoy staying right on Keiki beach. Walking distance to the Ironman start!
Villa
Kailua-Kona, HI, 96740, United States
0.4k from Kailua Pier center

AC, Dryer, Internet, Laundry, Living Area, No Smoking, Washer

5 Bedrooms14 Guests
New to Booking
$6592
Average price / night
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Kona Plaza#411
Kona Plaza#411
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier 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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Da KONA WEST 305 - listen to the ocean waves crashing !! 30 + days stays
Da KONA WEST 305 - listen to the ocean waves crashing !! 30 + days stays
Apartment
Kailua-Kona, HI, 96740, United States
0.4k from Kailua Pier center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

1 Bedroom2 Guests
9.8

Exceptional

29 reviews

$212
Average price / night
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Kona Plaza#221
Kona Plaza#221
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier 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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Sunsets and Tradewinds
Sunsets and Tradewinds
House
Kailua-Kona, HI, 96740, United States
0.5k from Kailua Pier center

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

1 Bedroom2 Guests
8.0

Good

2 reviews

$301
Average price / night
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Na Hale H2
Na Hale H2
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$494
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
0.5k from Kailua Pier center

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

4 Bedrooms12 Guests
8.6

Fabulous

7 reviews

$1192
Average price / night
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Kona Plaza#302
Kona Plaza#302
House
Kailua-Kona, HI, USA
0.3k from Kailua Pier 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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Spacious 8BR w/Ocean Views, Sleeps 16 with AC in fabulous Kailua-Kona
Spacious 8BR w/Ocean Views, Sleeps 16 with AC in fabulous Kailua-Kona
House
Kailua-Kona, HI, 96740, United States
0.5k from Kailua Pier center

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

8 Bedrooms16 Guests
New to Booking
$6582
Average price / night
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Big Island Kona Plaza 220 by Coldwell Banker Island Vacations
Big Island Kona Plaza 220 by Coldwell Banker Island Vacations
Apartment
Kailua-Kona, HI, USA
0.3k from Kailua Pier center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay

1 Bedroom4 Guests
New to Booking
$296
Average price / night
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Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates.
Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates.
House
Kailua Kona, HI, 96740, United States
0.5k from Kailua Pier center

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

3 Bedrooms8 Guests
9.2

Superb

80 reviews

$713
Average price / night
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🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town
🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town
House
Kailua Kona, HI, 96740, United States
0.5k from Kailua Pier center

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

5 Bedrooms10 Guests
9.8

Exceptional

54 reviews

$2363
Average price / night
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Aloha Lil Hawaiiana 🌺
Aloha Lil Hawaiiana 🌺
Apartment
Kailua, HI, 96740, United States
0.5k from Kailua Pier center

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

1 Bedroom2 Guests
8.8

Fabulous

5 reviews

$192
Average price / night
Check Availability
Downtown Kona Getaway | Ocean Views, Pool & Walk to Everything!
Downtown Kona Getaway | Ocean Views, Pool & Walk to Everything!
Apartment
Kailua-Kona, HI, 96740, United States
0.6k from Kailua Pier center

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

2 Bedrooms5 Guests
9.4

Superb

10 reviews

$328
Average price / night
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A Slice of Paradise in Kona - walk to stores, restaurants and the beach
A Slice of Paradise in Kona - walk to stores, restaurants and the beach
Apartment
Kailua-Kona, HI, 96740, United States
0.6k from Kailua Pier center

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

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$274
Average price / night
Check Availability
Oceanfront Retreat w/Sunset Views &  Paddleboards
Oceanfront Retreat w/Sunset Views & Paddleboards
House
Kailua-Kona, HI, 96740, United States
0.6k from Kailua Pier center

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

4 Bedrooms10 Guests
New to Booking
$3431
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Vacation Rentals in Kailua Pier.

Kailua Pier Vacation Rentals on the Map

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Frequently Asked Questions

There are a lot of options in Kailua Pier. If you plan on staying in the Kailua Pier area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Kailua Pier

You can explore 1509 verified vacation rentals in Kailua Pier. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Kailua Pier vary depending on the season, property size, and location. Rates typically start from around $172 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Kailua Pier include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Kailua Pier welcome pets. Currently, 3 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Kailua Pier often include amenities such as Wellness Facilities, Pool, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.