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)

Search 105,200+ Vacation Rentals

Kailua Waterfront Homes, Apartments & More - 79 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

79 Vacation rentals

Filters applied: Waterfront

(4)

1 / 26

Kailua House

  • 1
  • 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)

Book

from $228.00 / night

1 / 16

Kailua House

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

Responds fast! Avg. 1 hour 19 minutes

$325.00

Book

from $325.00 / night

1 / 17

Kailua House

  • 1
  • 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 41 minutes

$228.00

Book

from $228.00 / night

1 / 12

Kailua Apartment

  • 5
  • 10
  • min stay varies
  • Child friendly

$4,001.00

Inquire

from $4,001.00 / night

1 / 28

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,250.00

Inquire

from $1,250.00 / night

1 / 25

Kailua House

  • 6
  • 11
  • min stay varies
  • Child friendly
  • Private garden

$595.00

Inquire

from $595.00 / night

1 / 23

Kailua Apartment

  • 3
  • 7
  • 10 nights min
  • Child friendly

$650.00

Inquire

from $650.00 / night

1 / 16

Kailua House

  • 8
  • 16
  • 10 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$5,000.00

Inquire

from $5,000.00 / night

1 / 27

Kailua House

  • 5
  • 12
  • min stay varies
  • Child friendly

$1,500.00

Inquire

from $1,500.00 / night

1 / 26

Kailua House

  • 5
  • 12
  • min stay varies
  • Child friendly

$2,001.00

Inquire

from $2,001.00 / night

1 / 22

Kailua Apartment

  • 3
  • 8
  • 10 nights min
  • Child friendly

$795.00

Inquire

from $795.00 / night

1 / 28

Kailua Apartment

  • 4
  • 8
  • 10 nights min
  • Child friendly

$1,670.00

Inquire

from $1,670.00 / night

1 / 5

Kailua Apartment

  • 4
  • 7
  • 10 nights min
  • Child friendly

$585.00

Inquire

from $585.00 / night

1 / 31

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,750.00

Inquire

from $1,750.00 / night

1 / 7

Kailua Cottage

  • 1
  • 2
  • 3 nights min
  • Child friendly

$225.00

Inquire

from $225.00 / night

1 / 23

Kailua House

  • 4
  • 8
  • 10 nights min
  • Child friendly

$1,450.00

Inquire

from $1,450.00 / night

1 / 14

Kailua Villa

  • 4
  • 10
  • min stay varies
  • Child friendly

$900.00

Inquire

from $900.00 / night

1 / 14

Kailua House

  • 4
  • 8
  • 10 nights min
  • Child friendly

$1,500.00

Inquire

from $1,500.00 / night

Your search has been expanded 19.8 miles to include more rentals

1 / 21

Hawaii Kai House - 8.9 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$1,200.00

Inquire

from $1,200.00 / night

1 / 24

Kahala Apartment - 10.7 miles away

  • 2
  • 4
  • 90 nights min
  • Child friendly

$251.00

Inquire

from $251.00 / night

1 / 44

Kahala House - 9.6 miles away

  • 6
  • 15
  • 10 nights min
  • Child friendly

$1,700.00

Inquire

from $1,700.00 / night

1 / 29

Honolulu Condo - 10.1 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 18 minutes

$224.00

Book

from $224.00 / night

1 / 17

Hawaii Kai House - 8.1 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$850.00

Inquire

from $850.00 / night

1 / 22

Hawaii Kai Apartment - 9.7 miles away

  • 3
  • 6
  • 10 nights min
  • Child friendly

$650.00

Inquire

from $650.00 / night

1 / 25

Kahala House - 9.9 miles away

  • 5
  • 10
  • 10 nights min
  • Child friendly

$2,900.00

Inquire

from $2,900.00 / night

1 / 4

Honolulu House - 7.3 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,200.00

Inquire

from $1,200.00 / night

1 / 5

Hawaii Kai Townhouse - 8 miles away

  • 3
  • 5
  • 10 nights min
  • Child friendly

$450.00

Inquire

from $450.00 / night

1 / 27

Kahala House - 10.7 miles away

  • 6
  • 13
  • 10 nights min
  • Child friendly

$850.00

Inquire

from $850.00 / night

1 / 27

Honolulu Studio - 10.1 miles away

  • -1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 18 minutes

$224.00

Book

from $224.00 / night

1 / 43

Hawaii Kai House - 7.8 miles away

  • 7
  • 24
  • 10 nights min
  • Child friendly

$2,500.00

Inquire

from $2,500.00 / night

1 / 22

Hawaii Kai House - 8 miles away

  • 4
  • 10
  • min stay varies
  • Child friendly

$1,035.00

Inquire

from $1,035.00 / night

1 / 12

Honolulu Studio - 9.9 miles away

  • -1
  • 2
  • 3 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 52 minutes

$114.00

Book

from $114.00 / night

(3)

1 / 28

Laie House - 19.8 miles away

  • 4
  • 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)

Book

from $2,405.00 / night

(2)

1 / 10

Honolulu Condo - 9.9 miles away

  • 1
  • 5
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$107.00

Average (2 reviews)

Book

from $107.00 / night

1 / 20

Kahala House - 8.4 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$550.00

Inquire

from $550.00 / night

1 / 22

Hawaii Kai Apartment - 8 miles away

  • 5
  • 10
  • 10 nights min
  • Child friendly

$2,500.00

Inquire

from $2,500.00 / night

(22)

1 / 6

Honolulu Apartment - 10 miles away

  • 2
  • 8
  • 7 nights min
  • Child friendly

$441.00

Very Good (22 reviews)

Book

from $441.00 / night

(5)

1 / 39

Honolulu Villa - 9 miles away

  • 5
  • 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)

Book

from $343.00 / night

1 / 45

Honolulu House - 9.2 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

$6,000.00

Inquire

from $6,000.00 / night

1 / 40

Kahala House - 10 miles away

  • 8
  • 22
  • 7 nights min
  • Child friendly

$9,000.00

Inquire

from $9,000.00 / night