Search 105,200+ Vacation Rentals

Kailua 2-bedroom Homes, Apartments & More - 152 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

152 Vacation rentals

Filters applied: 2+ Bedrooms

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

$916.00

Book

from $916.00 / night

1 / 16

Kailua House

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

Responds fast! Avg. 1 hour 45 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)

1 / 29

Kailua House

  • 6
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
“We walked into the home and all 8 of us were stoked! The indoor spaciousness, the rooming out door meeting area was the ultimate and where we spend most if not all of our time while on site. I hope we have an opportunity to stay again in the future....”
- Review left on 02/06/2016

$1,495.00

Very Good (1 reviews)

Book

from $1,495.00 / night

1 / 33

Kailua Villa

  • 4
  • 10
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 55 minutes

$900.00

Book

from $900.00 / night

1 / 25

Kailua Villa

  • 5
  • 10
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 55 minutes

$4,500.00

Book

from $4,500.00 / night

1 / 37

Kailua Villa

  • 5
  • 14
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 55 minutes

$1,200.00

Book

from $1,200.00 / night

1 / 36

Kailua Apartment

  • 7
  • 14
  • 7 nights min
  • Child friendly

$9,500.00

Inquire

from $9,500.00 / night

1 / 23

Kailua Apartment

  • 3
  • 7
  • min stay varies
  • Child friendly

$650.00

Inquire

from $650.00 / night

1 / 28

Kailua House

  • 4
  • 8
  • 7 nights min
  • Child friendly

$1,250.00

Inquire

from $1,250.00 / night

1 / 26

Kailua Villa

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 55 minutes

$1,250.00

Book

from $1,250.00 / night

1 / 28

Kailua Apartment

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,670.00

Inquire

from $1,670.00 / night

1 / 14

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$900.00

Inquire

from $900.00 / night

1 / 26

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$2,000.00

Inquire

from $2,000.00 / 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

$695.00

Inquire

from $695.00 / night

1 / 27

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$1,500.00

Inquire

from $1,500.00 / night

1 / 14

Kailua Villa

  • 4
  • 10
  • min stay varies
  • Child friendly

$825.00

Inquire

from $825.00 / 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 / 5

Kailua Apartment

  • 4
  • 7
  • min stay varies
  • Child friendly

$585.00

Inquire

from $585.00 / night

1 / 34

Kailua House

  • 5
  • 9
  • min stay varies
  • Child friendly

$1,200.00

Inquire

from $1,200.00 / 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 19.8 miles to include more rentals

(46)

Certificate of Excellence

1 / 33

Honolulu Condo - 9.9 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 8 minutes

Certificate of Excellence

“We stay here for 6 nights in November 2016. The owners are very professional and the condo was spotless and all the amenities you could think of. The beds and all furnishing were top notch and very comfy. The views from the condo are spectacular....”
- Review left on 11/29/2016

$287.00

Excellent (46 reviews)

Book

from $287.00 / night

1 / 36

Laie House - 19.7 miles away

  • 10
  • 34
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

$1,804.00

Book

from $1,804.00 / night

(3)

1 / 16

Honolulu Condo - 9.8 miles away

  • 2
  • 6
  • 2 nights min
  • Nearest beach 0.3 mi
  • Child friendly
  • Car not necessary

$250.00

Very Good (3 reviews)

Book

from $250.00 / night

(1)

1 / 24

Waipahu House - 16.6 miles away

  • 3
  • 8
  • 4 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 10 minutes

$138.00

Excellent (1 reviews)

Book

from $138.00 / night

(1)

1 / 11

Honolulu Condo - 9.9 miles away

  • 2
  • 5
  • 3 nights min
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 4 minutes

$327.00

Excellent (1 reviews)

Book

from $327.00 / night

1 / 9

Hauula House - 18 miles away

  • 3
  • 8
  • min stay varies
  • Child friendly

$217.00

Book

from $217.00 / night

1 / 18

Hauula House - 19.1 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

$241.00

Book

from $241.00 / night

1 / 24

Hauula House - 18 miles away

  • 3
  • 10
  • min stay varies
  • Ask about children

$217.00

Book

from $217.00 / night

1 / 46

Hauula Condo - 16.5 miles away

  • 2
  • 8
  • min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

$258.00

Book

from $258.00 / night

(8)

1 / 26

Hauula House - 19 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning
“It must be noted that the caretaker of the house was extremely hospitable. When we checked in, I noticed there was fresh pineapple waiting for us on the dining table. It was one of the sweetest pineapples I have ever tasted. The home was clean,...”
- Review left on 08/14/2016

$274.00

Very Good (8 reviews)

Book

from $274.00 / night

(1)

1 / 60

Laie House - 19.8 miles away

  • 14
  • 34
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$4,208.00

Average (1 reviews)

Book

from $4,208.00 / night

1 / 31

Waimanalo House - 6.5 miles away

  • 6
  • 16
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

$2,296.00

Book

from $2,296.00 / night

1 / 30

Kahala Apartment - 8.5 miles away

  • 6
  • 11
  • 7 nights min
  • Child friendly

$2,500.00

Inquire

from $2,500.00 / night

1 / 35

Kahala House - 10.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$851.00

Inquire

from $851.00 / night

1 / 19

Kahala Apartment - 9.4 miles away

  • 5
  • 7
  • min stay varies
  • Child friendly

$1,200.00

Inquire

from $1,200.00 / night