Owner Direct Vacation Rentals in Kailua Beach

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  3.  USA

  4.  Hawaii

  5.  Kailua
  6.  Kailua Beach

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257 Kailua Beach Vacation Homes From $152

Looking for the ideal vacation rental in Kailua Beach? 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.

Beachfront spectacular Kailua beach
Beachfront spectacular Kailua beach
House
Kailua Beach, Kailua, Hawaii, USA
0.6k from Kailua Beach center

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

4 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$1224
Average price / night
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BAREFOOT BEACH RETREAT, 2BR, NEWLY FURN. WALK-2-BEACH/BUZZ'S=2 MIN, KAʻOHAO SCH.
BAREFOOT BEACH RETREAT, 2BR, NEWLY FURN. WALK-2-BEACH/BUZZ'S=2 MIN, KAʻOHAO SCH.
House
Honolulu, HI, 96734, United States
0.2k from Kailua Beach center

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

2 Bedrooms4 Guests
New to Booking
$292
Average price / night
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Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
1.0k from Kailua Beach center

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

3 Bedrooms6 Guests
New to Booking
$936
Average price / night
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Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
House
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

2 Bedrooms5 Guests
9.6

Exceptional

222 reviews

$828
Average price / night
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Beautiful Guest House Kailua Beach
Beautiful Guest House Kailua Beach
House
Kailua, HI, USA
1.4k from Kailua Beach center

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

1 Bedroom2 Guests
9.1

Superb

75 reviews

$284
Average price / night
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Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
Cottage
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

2 Bedrooms5 Guests
9.2

Superb

161 reviews

$628
Average price / night
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A Place of Peace Where Heaven Meets the Ocean
A Place of Peace Where Heaven Meets the Ocean
House
Kailua, HI, USA
1.5k from Kailua Beach center

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

2 Bedrooms4 Guests
New to Booking
$662
Average price / night
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Apartment
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

1 Bedroom3 Guests
9.6

Exceptional

158 reviews

$417
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Kailua Beach, Kailua, Hawaii, USA
1.7k from Kailua Beach 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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Kailua Beach \"The Pink House\"  100 Yards from Ocean
Kailua Beach \"The Pink House\" 100 Yards from Ocean
House
Kailua, HI, 96734, United States
0.2k from Kailua Beach center

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

4 Bedrooms6 Guests
10.0

Exceptional

81 reviews

$953
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
1.7k from Kailua Beach 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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The Modern Kailua Beach House
The Modern Kailua Beach House
House
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

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

3 Bedrooms6 Guests
New to Booking
$431
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
1.8k from Kailua Beach center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
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Luxury Beach Cottage in charming Kailua
Luxury Beach Cottage in charming Kailua
Cottage
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Laundry, Living Area

1 Bedroom6 Guests
New to Booking
$291
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
1.8k from Kailua Beach 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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The Cicak Shack - a perfect beach hideaway
The Cicak Shack - a perfect beach hideaway
Apartment
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Laundry, Living Area

1 Bedroom2 Guests
New to Booking
$184
Average price / night
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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
1.9k from Kailua Beach center

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

1 Bedroom4 Guests
New to Booking
$976
Average price / night
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Kahela - Paradise for Rent
Kahela - Paradise for Rent
House
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

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

4 Bedrooms8 Guests
9.8

Exceptional

51 reviews

$722
Average price / night
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Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
10.0

Exceptional

116 reviews

$742
Average price / night
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Secluded Beach Bungalow with Private Garden
Secluded Beach Bungalow with Private Garden
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

1 Bedroom2 Guests
10.0

Exceptional

33 reviews

$245
Average price / night
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Footsteps to Hawaii's Best Beach
Footsteps to Hawaii's Best Beach
Cottage
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

1 Bedroom2 Guests
10.0

Exceptional

55 reviews

$152
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 Beach.

Kailua Beach Vacation Rentals on the Map

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Frequently Asked Questions

There are a lot of options in Kailua Beach. If you plan on staying in the Kailua Beach 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 Beach

You can explore 257 verified vacation rentals in Kailua Beach. 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 Beach vary depending on the season, property size, and location. Rates typically start from around $152 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 Beach 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 Beach welcome pets. Currently, 12 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 Beach often include amenities such as View, Ocean View, and Balcony/Terrace. 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.