Kailua Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Kailua, Hawaii, USA

PRIVATE BEACHFRONT RENTAL
FromCA $649 per night
10.0 (168 Reviews)
1 Bedroom 2 Guests
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach!
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10.0 (1 Review)
3 Bedrooms 7 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Modern Luxury Beach House Kailua
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9.2 (87 Reviews)
3 Bedrooms 7 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (75 Reviews)
1 Bedroom 2 Guests
Available and legal for stays less than 30 days.
10.0 (112 Reviews)
1 Bedroom 2 Guests
Oahu Camper Adventures
FromCA $171 per night
9.1 (65 Reviews)
1 Bedroom 4 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromCA $1,673 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
KAILUA-STEPS TO THE BEACH
FromCA $262 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Enchanting Beach Bungalow with Private Garden
10.0 (80 Reviews)
1 Bedroom 2 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Kailua Beachside home
FromCA $2,584 per night
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New
4 Bedrooms 14 Guests
Upscale Kailua Getaway: Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
Beautiful Kailua Hale Studio
FromCA $513 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
A Place of Peace where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
Footsteps to Hawaii's Best Beach
FromCA $192 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromCA $183 per night
10.0 (45 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromCA $142 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromCA $1,334 per night
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New
1 Bedroom 4 Guests
Secluded Beach Bungalow with Private Garden
10.0 (32 Reviews)
1 Bedroom 2 Guests
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromCA $502 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromCA $537 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Entire Fantastic Kailua Cottage. waiting for you!
10.0 (17 Reviews)
1 Bedroom 3 Guests
Beautiful Beachside Bungalow
FromCA $502 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
10.0 (12 Reviews)
2 Bedrooms 2 Guests
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
10.0 (10 Reviews)
1 Bedroom 4 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Oahu Ohana Vans LLC
FromCA $410 per night
New
4 Bedrooms 4 Guests
Heavenly Hale Best monthly Vacation rental - walk to beach!
9.6 (4 Reviews)
2 Bedrooms 4 Guests
Absolutely Oceanfront - 60' Waterfall Lap Pool
9.4 (168 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (163 Reviews)
1 Bedroom 2 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (96 Reviews)
2 Bedrooms 4 Guests
Little Yellow Cottage: Steps to Lanikai Beach
9.4 (57 Reviews)
2 Bedrooms 4 Guests
Kailua Sands Getaway
FromCA $81 per night
9.4 (13 Reviews)
1 Bedroom 1 Guest
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
9.2 (154 Reviews)
2 Bedrooms 5 Guests
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
9.2 (104 Reviews)
4 Bedrooms 3 Guests
60 second walk to Lanikai Beach. 2 Bedrooms w/AC
9.0 (8 Reviews)
2 Bedrooms 4 Guests
Light and breezy Kailua apartment
9.0 (2 Reviews)
1 Bedroom 2 Guests
Ohana Rental Cottage Close to Beach
8.0 (4 Reviews)
2 Bedrooms 6 Guests
Private Luxury Home, Steps from the Beach w/AC, Ranch Beach House
8.0 (1 Review)
2 Bedrooms 4 Guests

About Kailua Vacation Rentals

With more than 459 Kailua vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Kailua.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Kailua, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Kailua. Places to stay near Kailua are 1293.64 ft² on average, with prices averaging CA $1,120 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Kailua with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Kailua?

What are the top vacation rentals in Kailua?

How many Rentbyowner vacation rentals are available in Kailua?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 459 in the Kailua area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Kailua. 

Nearby Neighborhood (7)

NeighborhoodProperty Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 115
Lanikai Vacation Rentals in Kailua, Hawaii 70
Coconut Grove Vacation Rentals in Kailua, Hawaii 499
Enchanted Lake Vacation Rentals in Kailua, Hawaii 456
Keolu Hills Vacation Rentals in Kailua, Hawaii 438
Kuulei Tract Vacation Rentals in Kailua, Hawaii 483
Palolo Vacation Rentals in Kailua, Hawaii 167