Owner Direct Vacation Rentals in Kailua Bay Beach

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251 Kailua Bay Beach Vacation Homes From $104

Looking for the ideal vacation rental in Kailua Bay 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.

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
0.5k from Kailua Bay 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
Check Availability
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
House
Kailua, HI, 96734, United States
0.3k from Kailua Bay Beach center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

1 Bedroom2 Guests
10.0

Exceptional

29 reviews

$307
Average price / night
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Beautiful Guest House Kailua Beach
Beautiful Guest House Kailua Beach
House
Kailua, HI, USA
0.6k from Kailua Bay 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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Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
House
Kailua, HI, 96734, United States
0.4k from Kailua Bay Beach center

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

3 Bedrooms10 Guests
10.0

Exceptional

37 reviews

$3546
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Kailua Bay Beach, Kailua, Hawaii, USA
0.7k from Kailua Bay 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 Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Villa
Kailua, HI, 96734, United States
0.4k from Kailua Bay Beach center

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

5 Bedrooms12 Guests
New to Booking
$2410
Average price / night
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Beachfront spectacular Kailua beach
Beachfront spectacular Kailua beach
House
Kailua Bay Beach, Kailua, Hawaii, USA
0.8k from Kailua Bay 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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Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi
Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

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

4 Bedrooms6 Guests
New to Booking
$502
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
0.9k from Kailua Bay Beach 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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 Celebrate America's 250th Birthday &  Kailua Fireworks from  Beachfront Lanai
Celebrate America's 250th Birthday & Kailua Fireworks from Beachfront Lanai
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

47 reviews

$1442
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
1.1k from Kailua Bay Beach 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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Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House
Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

AC, Balcony, Dryer, Free Parking, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
8.0

Good

1 reviews

$484
Average price / night
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Kalama Room
Kalama Room
Apartment
Kailua, HI, USA
1.2k from Kailua Bay Beach center

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

1 Bedroom2 Guests
New to Booking
$104
Average price / night
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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1390
Average price / night
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Private One Bedroom Side House close to Kailua
Private One Bedroom Side House close to Kailua
House
Kailua, HI, USA
1.4k from Kailua Bay Beach center

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

1 Bedroom2 Guests
3.5

Review score

2 reviews

$235
Average price / night
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Kailua Kai/Beach Front Licensed Rental #1990/NUC-1780
Kailua Kai/Beach Front Licensed Rental #1990/NUC-1780
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

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

4 Bedrooms10 Guests
9.6

Exceptional

137 reviews

$2697
Average price / night
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Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
1.4k from Kailua Bay Beach center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
Check Availability
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

AC, Balcony, Dryer, Free Parking, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

4 Bedrooms8 Guests
New to Booking
$910
Average price / night
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Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

AC, Balcony, Dryer, Free Parking, Kitchen, Laundry, No Smoking, Outdoor Space, Tennis Court

2 Bedrooms4 Guests
New to Booking
$636
Average price / night
Check Availability
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
House
Kailua, HI, 96734, United States
0.5k from Kailua Bay Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$441
Average price / night
Check Availability
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
House
Kailua, HI, 96734, United States
0.6k from Kailua Bay Beach center

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

3 Bedrooms7 Guests
New to Booking
$2309
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 Bay Beach.

Kailua Bay Beach Vacation Rentals on the Map

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Frequently Asked Questions

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

You can explore 251 verified vacation rentals in Kailua Bay 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 Bay Beach vary depending on the season, property size, and location. Rates typically start from around $104 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 Bay 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 Bay Beach welcome pets. Currently, 6 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 Bay Beach often include amenities such as Internet, 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.