Search Villas in Kailua

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Villas in Kailua

Luxurious Hawaiian Villa Oasis
Beach towels

Luxurious Hawaiian Villa Oasis

10.0 out of 10, Exceptional, (19)
"Would highly recommend this property. Both location, house, and property management team led by Inbar we're all top notch!!"
Luxurious Hawaiian Villa Oasis
Luxury Hawaii Kai Villa Luana – Ocean View, Saltwater Pool, 5 Min to Sandy Beach
Outdoor pool

Luxury Hawaii Kai Villa Luana – Ocean View, Saltwater Pool, 5 Min to Sandy Beach

Luxury Hawaii Kai Villa Luana – Ocean View, Saltwater Pool, 5 Min to Sandy Beach
3 Beachfront Spas|90"THTR|Only home in Hawaii with Private Beach|Jurassic Park F
Terrace/patio

3 Beachfront Spas|90"THTR|Only home in Hawaii with Private Beach|Jurassic Park F

10.0 out of 10, Exceptional, (23)
"Relaxing family vacation on the quiet side of the island."
3 Beachfront Spas|90"THTR|Only home in Hawaii with Private Beach|Jurassic Park F
TMV 5: 8bdrm,/7ba at Tiki Moon Villas
Exterior

TMV 5: 8bdrm,/7ba at Tiki Moon Villas

10.0 out of 10, Exceptional, (1)
"Jade a great time property was great and on a great area"
TMV 5: 8bdrm,/7ba at Tiki Moon Villas
Spacious Waterfront with Gorgeous View & Pool
Outdoor pool

Spacious Waterfront with Gorgeous View & Pool

10.0 out of 10, Exceptional, (8)
"Wonderful property with so much room inside house and amazing outside spaces. Our Family of 8 and young grandson had a great time. House sits on beautiful bay. Home set up for many activities."
Spacious Waterfront with Gorgeous View & Pool
Poolside Paradise: with Double Bay View Rooms (Unit C)
Private kitchen

Poolside Paradise: with Double Bay View Rooms (Unit C)

Poolside Paradise: with Double Bay View Rooms (Unit C)
Spacious Studio Suite With Office (Unit A)
Private kitchen

Spacious Studio Suite With Office (Unit A)

Spacious Studio Suite With Office (Unit A)
Hale Ohana - Beachfront, Pool, AC
Pool

Hale Ohana - Beachfront, Pool, AC

2.0 star property
8.0 out of 10, Very Good, (1)
"The property is stunning. There is very little to no help once you arrive. There are numerous things on the property That are somewhat challenging to operate. Don't expect any help learning how to work any of the electronics or ask any basic questions. But with that said, the property is amazing."
Hale Ohana - Beachfront, Pool, AC
King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)
Private kitchen

King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)

King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)
Moana Vista by AvantStay | Private Beach + Views
Terrace/patio

Moana Vista by AvantStay | Private Beach + Views

Moana Vista by AvantStay | Private Beach + Views
Poolside Paradise: with Double Bay View Rooms (Unit C)
Private kitchen

Poolside Paradise: with Double Bay View Rooms (Unit C)

Poolside Paradise: with Double Bay View Rooms (Unit C)
Spacious Suite With Office (Unit A)
Private kitchen

Spacious Suite With Office (Unit A)

Spacious Suite With Office (Unit A)
Relaxing 3-br/2.5ba villa with pool and tiki bar
Outdoor dining

Relaxing 3-br/2.5ba villa with pool and tiki bar

3.0 star property
Relaxing 3-br/2.5ba villa with pool and tiki bar
Ocean Breeze: 1bdrm/1ba at Tiki Moon Villas
Outdoor dining

Ocean Breeze: 1bdrm/1ba at Tiki Moon Villas

9.0 out of 10, Wonderful, (6)
"Loved the location, we saw whales in the morning. GREAT food places close by, embrace food trucks. Bed was comfortable. Kitchen is minimal. But who’s there for the kitchen? The patio is wonderful, get up and enjoy the sunrises just outside your door. Beach accessories were good quality, we appreciate the chairs especially. We were greeted at the start of our stay and saw the property manager repeatedly with regular checkins. Our only ‘would do differently’ is renting the car through the...
Ocean Breeze: 1bdrm/1ba at Tiki Moon Villas
King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)
Private kitchen

King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)

King Suite Oasis: Unwind with Jacuzzi & Bay Views (Unit B)
Luxury Villa in Beachfront Estate In Kailua
On the beach, beach towels

Luxury Villa in Beachfront Estate In Kailua

2.0 star property
Luxury Villa in Beachfront Estate In Kailua
Luxurious Paradise on Marina
Exterior

Luxurious Paradise on Marina

4.0 star property
Luxurious Paradise on Marina
Moana Vista by Avantstay Private Beach Views
Villa

Moana Vista by Avantstay Private Beach Views

2.0 star property
Moana Vista by Avantstay Private Beach Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your villa in Kailua with Expedia?
We think arranging a vacation shouldn’t be hard, so if you’re searching for villas at a competitive rate, Expedia delivers. Save those pennies and opt for an all-inclusive stay, or splurge on a plush villa to spoil your favorite people. Use our convenient search filters to find a property in Kailua that fits your needs.
How can I find cheap villas in Kailua?
A fantastic way to track down cheap villas in Kailua is with Expedia’s filter tool. Narrow your search results by star rating, budget and amenities to grab awesome deals in just a few clicks.