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

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  4.  Hawaii

  5.  Kailua

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242 Best Vacation Rentals in Kailua (Starting from $104)

Beautiful Guest House Kailua Beach
Beautiful Guest House Kailua Beach
House
Kailua, HI, USA
0.1k from Kailua 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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Kakela Kai, Beachfront Kailua Home, Private, A/C
Kakela Kai, Beachfront Kailua Home, Private, A/C
House
Kailua, HI, 96734, United States
0.1k from Kailua center

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

4 Bedrooms10 Guests
10.0

Exceptional

14 reviews

$1099
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Kailua, Hawaii, USA
0.2k from Kailua 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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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
0.1k from Kailua center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$347
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
0.4k from Kailua 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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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
0.2k from Kailua center

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

4 Bedrooms6 Guests
New to Booking
$480
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
0.8k from Kailua 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
0.2k from Kailua center

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

4 Bedrooms10 Guests
9.6

Exceptional

134 reviews

$2734
Average price / night
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Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
0.8k from Kailua center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
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'Star of Hawaii'  Beachside, Pool, Steps to Beach - Great for Families
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
House
Kailua, HI, 96734, United States
0.2k from Kailua center

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

4 Bedrooms10 Guests
9.4

Superb

98 reviews

$669
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
0.9k from Kailua 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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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
0.3k from Kailua center

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

2 Bedrooms4 Guests
8.0

Good

1 reviews

$405
Average price / night
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Beachfront spectacular Kailua beach
Beachfront spectacular Kailua beach
House
Kailua, Hawaii, USA
0.9k from Kailua 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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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
0.3k from Kailua center

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

3 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$3308
Average price / night
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Kailani Loft, Kailua Coconut Grove 1-bedroom
Kailani Loft, Kailua Coconut Grove 1-bedroom
Apartment
Kailua, HI, USA
0.9k from Kailua center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom3 Guests
9.3

Superb

47 reviews

$193
Average price / night
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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
0.3k from Kailua center

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

4 Bedrooms8 Guests
New to Booking
$715
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
0.9k from Kailua 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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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
0.3k from Kailua center

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

2 Bedrooms4 Guests
New to Booking
$579
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
0.9k from Kailua 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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 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
0.4k from Kailua center

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

4 Bedrooms8 Guests
10.0

Exceptional

47 reviews

$1466
Average price / night
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Kalama Room
Kalama Room
Apartment
Kailua, HI, USA
1.0k from Kailua 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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Happy House on Exquisite Kailua Beachside Property!
Happy House on Exquisite Kailua Beachside Property!
House
Kailua, HI, 96734, United States
0.4k from Kailua center

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

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$583
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
0.4k from Kailua center

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

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1142
Average price / night
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Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
House
Kailua, HI, 96734, United States
0.4k from Kailua center

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

1 Bedroom2 Guests
10.0

Exceptional

29 reviews

$314
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 center

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

5 Bedrooms12 Guests
New to Booking
$2363
Average price / night
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Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Apartment
Kailua, HI, 96734, United States
0.5k from Kailua center

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

2 Bedrooms3 Guests
New to Booking
$282
Average price / night
Check Availability
Available and legal for stays less than 30 days.
Available and legal for stays less than 30 days.
Apartment
Kailua, HI, 96734, United States
0.5k from Kailua center

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

1 Bedroom2 Guests
10.0

Exceptional

112 reviews

$344
Average price / night
Check Availability

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.

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Frequently Asked Questions

You can explore 242 verified vacation rentals in Kailua. 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 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 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 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 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.