Search 105,200+ Vacation Rentals

Kailua Waterfront Homes, Apartments & More - 165 Rentals Available.

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

165 Vacation rentals

Filters applied: Waterfront

(4)

1 / 26

Kailua House

  • 1
  • 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$343.00

Very Good (4 reviews)

Book

from $343.00 / night

1 / 17

Kailua House

  • 3
  • 8
  • min stay varies
  • Nearest beach 6 mi
  • Ask about children
  • Air conditioning

$378.00

Book

from $378.00 / night

1 / 32

Kailua House

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$5,411.00

Book

from $5,411.00 / night

1 / 59

Kailua House

  • 3
  • 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$917.00

Book

from $917.00 / night

1 / 16

Kailua House

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 7 minutes

$630.00

Book

from $630.00 / night

(1)

1 / 21

Kailua House

  • 5
  • 10
  • min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly
“Perfect location, right on the ocean which made for spectacular views. The house was large and accommodating, and mostly clean. The sliding doors/screens to the outside were definitely worn and old and hard to open/close. We did find a few (dead)...”
- Review left on 01/04/2017

$1,226.00

Very Good (1 reviews)

Book

from $1,226.00 / night

1 / 12

Kailua House

  • 1
  • 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$252.00

Book

from $252.00 / night

1 / 23

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,250.00

Inquire

from $1,250.00 / night

1 / 22

Kailua Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

$795.00

Inquire

from $795.00 / night

1 / 28

Kailua Apartment

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,670.00

Inquire

from $1,670.00 / night

1 / 7

Kailua Cottage

  • 1
  • 2
  • 3 nights min
  • Child friendly

$225.00

Inquire

from $225.00 / night

1 / 26

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$2,000.00

Inquire

from $2,000.00 / night

1 / 31

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,751.00

Inquire

from $1,751.00 / night

1 / 23

Kailua Apartment

  • 3
  • 7
  • min stay varies
  • Child friendly

$675.00

Inquire

from $675.00 / night

1 / 14

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$900.00

Inquire

from $900.00 / night

1 / 34

Kailua House

  • 5
  • 9
  • min stay varies
  • Child friendly

$1,200.00

Inquire

from $1,200.00 / night

1 / 27

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$1,500.00

Inquire

from $1,500.00 / night

1 / 36

Kailua Apartment

  • 7
  • 14
  • 7 nights min
  • Child friendly

$9,500.00

Inquire

from $9,500.00 / night

1 / 28

Kailua House

  • 4
  • 8
  • 7 nights min
  • Child friendly

$1,250.00

Inquire

from $1,250.00 / night

1 / 5

Kailua Apartment

  • 4
  • 7
  • min stay varies
  • Child friendly

$585.00

Inquire

from $585.00 / night

1 / 16

Kailua House

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,500.00

Inquire

from $4,500.00 / night

1 / 14

Kailua Villa

  • 4
  • 10
  • min stay varies
  • Child friendly

$826.00

Inquire

from $826.00 / night

1 / 28

Kailua House

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,200.00

Inquire

from $1,200.00 / night

1 / 39

Kailua Villa

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$6,000.00

Inquire

from $6,000.00 / night

Your search has been expanded 19.1 miles to include more rentals

1 / 35

Kahala House - 10.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$850.00

Inquire

from $850.00 / night

1 / 29

Kahala Villa - 8.9 miles away

  • 5
  • 12
  • min stay varies
  • Child friendly

$890.00

Inquire

from $890.00 / night

(1)

1 / 28

Hauula House - 18.6 miles away

  • 3
  • 10
  • min stay varies
  • Ask about children
“It was very warm inside the house, but the drinking outside was hilarious, even though you cannot, you should atleast put it inside a cup. Other wise it was awesome here, so thank you JENNA for your hard work and communication with me. YES I would...”
- Review left on 07/13/2016

$228.00

Very Good (1 reviews)

Book

from $228.00 / night

1 / 34

Kaneohe House - 3.6 miles away

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$973.00

Book

from $973.00 / night

1 / 32

Hawaii Kai Apartment - 7.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,250.00

Inquire

from $1,250.00 / night

1 / 20

Hauula House - 16 miles away

  • 2
  • 6
  • min stay varies
  • Ask about children

$183.00

Book

from $183.00 / night

1 / 20

Kahala House - 8.4 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$10.00

Inquire

from $10.00 / night

(1)

1 / 51

Honolulu Condo - 9.9 miles away

  • 1
  • 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The studio was conveniently located within walking distance of the Ala Moana Mall and away from the busiest part of Waikiki. The check-in/check-out process was very organized and easy. The room was clean when we arrived. It is smaller than...”
- Review left on 06/21/2013

$167.00

Very Good (1 reviews)

Book

from $167.00 / night

1 / 17

Hawaii Kai House - 8.1 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$795.00

Inquire

from $795.00 / night

1 / 40

Kahala House - 10 miles away

  • 8
  • 22
  • 7 nights min
  • Child friendly

$9,000.00

Inquire

from $9,000.00 / night

(1)

1 / 26

Hauula Condo - 16.5 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$132.00

Excellent (1 reviews)

Book

from $132.00 / night

(9)

1 / 23

Honolulu Apartment - 9.7 miles away

  • 1
  • 4
  • 30 nights min
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 31 minutes

“The room was located in the center of Waikiki and you could walk to ALL attractions with out needing a rental car. I did get a rental car for a couple days to see all of Oahu and Enterprise is located on the first floor of the building! The cost...”
- Review left on 09/26/2016

$62.00

Very Good (9 reviews)

Book

from $62.00 / night

1 / 25

Kahala House - 9.9 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$2,500.00

Inquire

from $2,500.00 / night

(4)

1 / 34

Hauula House - 19.1 miles away

  • 5
  • 17
  • min stay varies
  • Ask about children
“Was perfect for our family The kitchen was exactly the size we needed. And it was close to all the beaches we love and the Polynesian cultural center. It was easy to reserve and our agent was very helpful...”
- Review left on 12/02/2016

$469.00

Excellent (4 reviews)

Book

from $469.00 / night

1 / 15

Kahala Apartment - 10.3 miles away

  • 3
  • 2
  • min stay varies
  • Child friendly

$2,500.00

Inquire

from $2,500.00 / night

1 / 36

Honolulu Condo - 10 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly

$1,500.00

Inquire

from $1,500.00 / night