Vacation Rentals in Kailua Beach, HI: Compare 10+ Sites & Save

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252 Best Vacation Rentals in Kailua Beach (Starting from $140)

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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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

218 reviews

$646
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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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
9.4

Superb

151 reviews

$522
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 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

149 reviews

$373
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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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

79 reviews

$765
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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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
$454
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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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
$284
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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Romantic Oceanview Guesthouse.  Steps from the Beach!
Romantic Oceanview Guesthouse. Steps from the Beach!
Apartment
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

AC, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, TV

1 Bedroom2 Guests
9.8

Exceptional

170 reviews

$290
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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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

$665
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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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

115 reviews

$678
Average price / night
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Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Apartment
Kailua, HI, USA
2.1k from Kailua Beach center

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

2 Bedrooms4 Guests
New to Booking
$219
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

32 reviews

$250
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
2.2k from Kailua 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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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

$140
Average price / night
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Enchanting Beach Bungalow with Private Garden
Enchanting Beach Bungalow with Private Garden
Apartment
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

80 reviews

$316
Average price / night
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The Banyan Beach Bungalow
The Banyan Beach Bungalow
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

1 Bedroom2 Guests
10.0

Exceptional

26 reviews

$366
Average price / night
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Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$774
Average price / night
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Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

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

1 Bedroom4 Guests
New to Booking
$293
Average price / night
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Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1641
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 Vacation Rentals in Kailua Beach.

Where to stay in Kailua Beach? Best neighborhoods & areas

Kailua Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 252 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 $140 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, 10 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 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.