COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

- Travelers
- Owners / Managers
Help
Deals
Discover
Manage your booking
$ USD

Travelers

Sign in
Join
Manage your booking
$ USD
Help
Deals

Owners

Owner login
List your property
Help

Search 105,200+ Vacation Rentals

Where do you want to go? ✕

Check in

Check out

Sleeps

Adults

Children

Sleeps

Search

All Vacation Rentals

Kailua Vacation Rentals

Kailua Waterfront Homes, Apartments & More - 79 Rentals Available.

Min price

Max price

Bedrooms

Adults

Children

More Filters Fewer Filters

Air conditioning (4)
Balcony or terrace (2)
DVD player (4)
Dishwasher (13)
Garden (4)
Grill (15)
Heated pool (1)
High Speed Internet (5)
High chair (3)
Hot tub/Jacuzzi (2)
Private pool (3)
Swimming pool (4)
Washing machine (7)
Wi-Fi available (4)

More

Less

Apartment (5)
Cottage (1)
House (11)
Villa (1)

More

Less

Payment Protection

To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

79 Vacation rentals

Sort by:

Filters applied: Waterfront

Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 26

Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $199

Kailua House

1 bedroom 1
1 bathroom
sleeps 2 2
3 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 2 hours 52 minutes

“My stay was delightful in this one bedroom apartment. My view of the ocean was spectacular. Everything was meticulous and I couldn't have been more pleased. The full obscure blinds on the windows when the sun was shining in were a real benefit to...”

- Review left on 01/07/2017

$228.00

Very Good (4 reviews)

from $228.00 / night

Book

1 / 16

Kailua Surf Paradise Hale, pool

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 19 minutes

$325.00

from $325.00 / night

Book

1 / 17

Absolutely Oceanfront - NOW $199 -Kailua Studio with 2 decks - Legal

Kailua House

1 bedroom 1
1 bathroom
sleeps 2 2
3 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 2 hours 41 minutes

$228.00

from $228.00 / night

Book

1 / 12

Large Private Luxury Home w/Pool, A/C and Ocean Views. Kailua Shores Estate

Kailua Apartment

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Child friendly

$4,001.00

from $4,001.00 / night

Inquire

1 / 28

Kailua Beach House

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Child friendly

$1,250.00

from $1,250.00 / night

Inquire

1 / 25

Beach House w/amazing ocean views & 10 steps from beach access. Hale Kalio

Kailua House

6 bedrooms 6
4 bathrooms
sleeps 11 11
min stay varies

Child friendly
Private garden

$595.00

from $595.00 / night

Inquire

1 / 23

Lanikai Cottage

Kailua Apartment

3 bedrooms 3
2 bathrooms
sleeps 7 7
10 nights min

Child friendly

$650.00

from $650.00 / night

Inquire

1 / 16

Kailua Shores Estate 8 Bedroom

Kailua House

8 bedrooms 8
9 bathrooms
sleeps 16 16
10 nights min

Swimming pool
Child friendly
Air conditioning

$5,000.00

from $5,000.00 / night

Inquire

1 / 27

Lanikai Breeze

Kailua House

5 bedrooms 5
5 bathrooms
sleeps 12 12
min stay varies

Child friendly

$1,500.00

from $1,500.00 / night

Inquire

1 / 26

Lanikai Oceanside 5 Bedroom

Kailua House

5 bedrooms 5
4 bathrooms
sleeps 12 12
min stay varies

Child friendly

$2,001.00

from $2,001.00 / night

Inquire

1 / 22

Hale Nani Lanikai

Kailua Apartment

3 bedrooms 3
4 bathrooms
sleeps 8 8
10 nights min

Child friendly

$795.00

from $795.00 / night

Inquire

1 / 28

Maluhia

Kailua Apartment

4 bedrooms 4
4 bathrooms
sleeps 8 8
10 nights min

Child friendly

$1,670.00

from $1,670.00 / night

Inquire

1 / 5

Ke'aloha

Kailua Apartment

4 bedrooms 4
3 bathrooms
sleeps 7 7
10 nights min

Child friendly

$585.00

from $585.00 / night

Inquire

1 / 31

Lanikai Oceanside 4 Bedroom - Lanikai Kailua Oceanfront Beach House

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Child friendly

$1,750.00

from $1,750.00 / night

Inquire

1 / 7

Lanikai Ohana Hale

Kailua Cottage

1 bedroom 1
1 bathroom
sleeps 2 2
3 nights min

Child friendly

$225.00

from $225.00 / night

Inquire

1 / 23

Lanikai Ocean View Villa

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 8 8
10 nights min

Child friendly

$1,450.00

from $1,450.00 / night

Inquire

1 / 14

Hale Kimo

Kailua Villa

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Child friendly

$900.00

from $900.00 / night

Inquire

1 / 14

Kailani Villa

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 8 8
10 nights min

Child friendly

$1,500.00

from $1,500.00 / night

Inquire

Your search has been expanded 19.8 miles to include more rentals

1 / 21

Hale Kai

Hawaii Kai House - 8.9 miles away

5 bedrooms 5
4 bathrooms
sleeps 10 10
min stay varies

Child friendly

$1,200.00

from $1,200.00 / night

Inquire

1 / 24

Executive Gold Coast Oceanfront Suite

Kahala Apartment - 10.7 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
90 nights min

Child friendly

$251.00

from $251.00 / night

Inquire

1 / 44

Hokulani

Kahala House - 9.6 miles away

6 bedrooms 6
6 bathrooms
sleeps 15 15
10 nights min

Child friendly

$1,700.00

from $1,700.00 / night

Inquire

1 / 29

STUDIO WAIKIKI NEW YEARS WAIKIKI CONDO-5* LOCATION- USE OF PENTHOUSE LOUNGE

Honolulu Condo - 10.1 miles away

1 bedroom 1
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly
Car not necessary

Responds fast! Avg. 2 hours 18 minutes

$224.00

from $224.00 / night

Book

1 / 17

Hale Laulea

Hawaii Kai House - 8.1 miles away

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Child friendly

$850.00

from $850.00 / night

Inquire

1 / 22

Lumahai Hale

Hawaii Kai Apartment - 9.7 miles away

3 bedrooms 3
3 bathrooms
sleeps 6 6
10 nights min

Child friendly

$650.00

from $650.00 / night

Inquire

1 / 25

Kahala Grand Splendor

Kahala House - 9.9 miles away

5 bedrooms 5
4 bathrooms
sleeps 10 10
10 nights min

Child friendly

$2,900.00

from $2,900.00 / night

Inquire

1 / 4

Casa de Makalei

Honolulu House - 7.3 miles away

4 bedrooms 4
5 bathrooms
sleeps 8 8
min stay varies

Child friendly

$1,200.00

from $1,200.00 / night

Inquire

1 / 5

Ohana Kai

Hawaii Kai Townhouse - 8 miles away

3 bedrooms 3
3 bathrooms
sleeps 5 5
10 nights min

Child friendly

$450.00

from $450.00 / night

Inquire

1 / 27

Hale Makalei

Kahala House - 10.7 miles away

6 bedrooms 6
5 bathrooms
sleeps 13 13
10 nights min

Child friendly

$850.00

from $850.00 / night

Inquire

1 / 27

STUDIO WAIKIKI BEACHNEW YEARS USE OF OWNERS PENTHOUSE,100 ft BEACH 5* LOCATION

Honolulu Studio - 10.1 miles away

Studio -1
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly
Car not necessary

Responds fast! Avg. 2 hours 18 minutes

$224.00

from $224.00 / night

Book

1 / 43

Paiko Lagoon Retreat

Hawaii Kai House - 7.8 miles away

7 bedrooms 7
5 bathrooms
sleeps 24 24
10 nights min

Child friendly

$2,500.00

from $2,500.00 / night

Inquire

1 / 22

Hale Niuiki

Hawaii Kai House - 8 miles away

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Child friendly

$1,035.00

from $1,035.00 / night

Inquire

1 / 12

Panoramic Ocean View- NOW $99 -Upgraded studio-Kitchenette- #3704

Honolulu Studio - 9.9 miles away

Studio -1
1 bathroom
sleeps 2 2
3 nights min

Nearest beach 20 mi
Swimming pool
Child friendly

Responds fast! Avg. 2 hours 52 minutes

$114.00

from $114.00 / night

Book

1 / 28

Hale Koa Estate - beachfront, w/ pool

Laie House - 19.8 miles away

4 bedrooms 4
5 bathrooms
sleeps 10 10
3 nights min

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

Responds fast! Avg. 3 hours 11 minutes

“This gorgeous home was the perfect location for our family vacation! Three generations under one roof and we never felt crowded. The pool, the beach, the yard, huge bedrooms. Really, it was perfection and I look forward to returning...”

- Review left on 09/04/2016

$2,405.00

Very Good (3 reviews)

from $2,405.00 / night

Book

1 / 10

Popular Waikiki Banyan One Bedroom With Parking

Honolulu Condo - 9.9 miles away

1 bedroom 1
1 bathroom
sleeps 5 5
30 nights min

Swimming pool
Ask about children
Air conditioning

$107.00

Average (2 reviews)

from $107.00 / night

Book

1 / 20

Hale Poola

Kahala House - 8.4 miles away

5 bedrooms 5
3 bathrooms
sleeps 10 10
min stay varies

Child friendly

$550.00

from $550.00 / night

Inquire

1 / 22

Moana Lani

Hawaii Kai Apartment - 8 miles away

5 bedrooms 5
6 bathrooms
sleeps 10 10
10 nights min

Child friendly

$2,500.00

from $2,500.00 / night

Inquire

1 / 6

Wyndham Waikiki Beach Walk

Honolulu Apartment - 10 miles away

2 bedrooms 2
2 bathrooms
sleeps 8 8
7 nights min

Child friendly

$441.00

Very Good (22 reviews)

from $441.00 / night

Book

1 / 39

AlohaPalace com 3-story OceanView w/Cottage,Pool & Elevator. 30 Day Minimum Stay

Honolulu Villa - 9 miles away

5 bedrooms 5
6 bathrooms
sleeps 25 25
min stay varies

Nearest beach 0.5 mi
Swimming pool
Child friendly

“What a blessing we had finding this home to rent for our large family reunion/vacation! We had 22 of our family members join us to celebrate our 50th wedding anniversary! The house fit our needs perfectly & Milan was an amazing host & a resource...”

- Review left on 10/26/2017

$343.00

Excellent (5 reviews)

from $343.00 / night

Book

1 / 45

Ocean House

Honolulu House - 9.2 miles away

6 bedrooms 6
7 bathrooms
sleeps 12 12
min stay varies

Child friendly

$6,000.00

from $6,000.00 / night

Inquire

1 / 40

Banyan House

Kahala House - 10 miles away

8 bedrooms 8
8 bathrooms
sleeps 22 22
7 nights min

Child friendly

$9,000.00

from $9,000.00 / night

Inquire

Page 1 of 2

1 2 Next Last

This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

What is Certificate of Excellence?

TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.

Looking for vacation inspiration?

Get the best deals and personalised recommendations, straight to your inbox (you can unsubscribe at any time).

The field must contain a valid email address.

Terms of use | Privacy policy

Discover

Rental type
Worldwide destinations
- Siesta Key
- Hawaii
- Key West
- Florida Keys
- Clearwater Beach
- Outer Banks
- Miami Beach
- Maui
- Naples
Other suggestions

Find a Rental
About Us
Terms

Copyright© 2020 Vacation Home Rentals. All rights reserved

See the details for this home, contact the owner, pay for your trip and more!

Go to manage your vacation booking

1

Need to think it over?

Send yourself an email so you can come back to book this property.

Enter your email address

The Enter your email address field is required. The "Enter your email address" field must contain a valid email address.

Privacy Policy

To get help making a booking, call our dedicated Reservations team at:

+1-857-504-6968

+1-857-504-6968

Monday to Friday - 7:00 to 23:30 UTC Weekends - 7:00 to 20:00 UTC