408+ Kailua Holiday Rentals & Private Villas
When do you want to travel?
We search multiple sites to find you the best prices.
10.0
(111 Reviews)
- Air Conditioner
- Parking
- Pool
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House
9.1
(85 Reviews)
- Parking
- View
- Ocean View
10.0
(1 Review)
- Air Conditioner
- Parking
- TV
10.0
(72 Reviews)
- Air Conditioner
- Parking
- TV
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House
9.1
(75 Reviews)
- Parking
- View
- Balcony/Terrace
9.8
(73 Reviews)
- Air Conditioner
- Parking
- Pool
9.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
9.8
(44 Reviews)
- Parking
- Pool
- TV
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Apartment
8.6
(52 Reviews)
- Air Conditioner
- Parking
- View
10.0
(228 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(134 Reviews)
- Air Conditioner
- Parking
- TV
10.0
(120 Reviews)
- Air Conditioner
- Parking
- TV
9.8
(76 Reviews)
- Air Conditioner
- Parking
- Pool
9.8
(76 Reviews)
- Air Conditioner
- Parking
- TV
9.6
(44 Reviews)
- Air Conditioner
- Parking
- Pool
9.4
(168 Reviews)
- Air Conditioner
- Parking
- Pool
9.4
(163 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(21 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(8 Reviews)
- Air Conditioner
- Parking
- TV
9.2
(20 Reviews)
- Air Conditioner
- Parking
- Pool
New
- Air Conditioner
- Parking
- TV
10.0
(101 Reviews)
- Parking
- TV
- View
10.0
(88 Reviews)
- Air Conditioner
- Parking
- Pool
10.0
(76 Reviews)
- Air Conditioner
- Parking
- TV
Frequently Asked Questions About Kailua Holiday Homes
What are the top rated Holiday Home Rentals in Kailua?
There are a lot of options in Kailua. If you plan on staying in the Kailua area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Kailua:
- Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
- Available and legal for stays less than 30 days.
- Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
- KAILUA-STEPS TO THE BEACH
- Enchanting Beach Bungalow with Private Garden
- Kailua Beach "The Pink House" 100 Yards from Ocean
- The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!
- BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
- Since 1985 Legal Lanikai Garden Studio AC, across the street from Lanikai Beach!
- Steps to Beach- Heated Pool- AC-Minimum Stay 7 Nights-CONTACT HOST
Which are the best holiday rentals in Kailua, HI?
There are many holiday rentals available in Kailua; however, here are a few of the most popular holiday homes listed in Kailua on our website:
What are the most family-friendly holiday homes in or near Kailua?
At Pacificislands most of our places to stay are perfect for families. Check out the complete list of holiday homes in Kailua to find one that works for you.
Can we get a self-catering family vacation rental in Kailua?
Yes, there are 408 self-catering family homes and holiday rentals in Kailua.
What are the top luxury holiday homes near Kailua?
There are more than 408 luxury holiday homes in or near Kailua, according to 2026 data from Pacificislands. Consider these homes for your next holiday:
