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Kailua Waterfront Homes, Apartments & More - 199 Rentals Available.

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199 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)

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from $343.00 / night

1 / 17

Kailua House

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

$378.00

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from $378.00 / night

1 / 32

Kailua House

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

$5,411.00

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from $5,411.00 / night

1 / 59

Kailua House

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

$916.00

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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

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from $630.00 / night

1 / 12

Kailua House

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

$252.00

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from $252.00 / 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)

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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)

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from $1,495.00 / night

1 / 25

Kailua Villa

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

Responds fast! Avg. 1 hour 1 minutes

$900.00

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from $900.00 / night

1 / 25

Kailua Villa

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

Responds fast! Avg. 1 hour 1 minutes

$4,500.00

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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 1 minutes

$1,200.00

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from $1,200.00 / night

1 / 26

Kailua Villa

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

Responds fast! Avg. 1 hour 1 minutes

$1,250.00

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from $1,250.00 / night

1 / 7

Kailua Cottage

  • 1
  • 2
  • 3 nights min
  • Child friendly

$225.00

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from $225.00 / night

1 / 28

Kailua Apartment

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,670.00

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from $1,670.00 / night

1 / 26

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$2,000.00

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from $2,000.00 / night

1 / 16

Kailua House

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

$4,500.00

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from $4,500.00 / night

1 / 32

Kailua Villa

  • 1
  • 10
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 1 minutes

$2,000.00

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from $2,000.00 / night

1 / 14

Kailua Villa

  • 4
  • 10
  • min stay varies
  • Child friendly

$795.00

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from $795.00 / night

1 / 27

Kailua House

  • 5
  • 12
  • 7 nights min
  • Child friendly

$1,500.00

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from $1,500.00 / night

1 / 34

Kailua House

  • 5
  • 9
  • min stay varies
  • Child friendly

$1,200.00

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from $1,200.00 / night

1 / 28

Kailua House

  • 4
  • 8
  • 7 nights min
  • Child friendly

$1,250.00

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from $1,250.00 / night

1 / 23

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$1,250.00

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from $1,250.00 / night

1 / 23

Kailua Apartment

  • 3
  • 7
  • min stay varies
  • Child friendly

$650.00

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from $650.00 / night

1 / 14

Kailua House

  • 4
  • 8
  • min stay varies
  • Child friendly

$900.00

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from $900.00 / night

1 / 36

Kailua Apartment

  • 7
  • 14
  • 7 nights min
  • Child friendly

$9,500.00

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from $9,500.00 / night

1 / 5

Kailua Apartment

  • 4
  • 7
  • min stay varies
  • Child friendly

$585.00

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from $585.00 / night

1 / 22

Kailua Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

$695.00

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from $695.00 / night

1 / 28

Kailua House

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

$1,200.00

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from $1,200.00 / night

1 / 39

Kailua Villa

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

$6,000.00

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from $6,000.00 / night

Your search has been expanded 19 miles to include more rentals

(22)

1 / 25

Honolulu Condo - 9.9 miles away

  • 1
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 23 minutes

“We really enjoyed staying here. The condo was the perfect size for 4 of us and it was just a few minute walk to the beach. The views are amazing. I love the floor to ceiling windows in the bedroom, and the fact that the bedroom windows open so I...”
- Review left on 05/24/2017

$183.00

Excellent (22 reviews)

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from $183.00 / night

1 / 34

Kaneohe House - 3.6 miles away

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

$1,145.00

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from $1,145.00 / night

(1)

1 / 11

Honolulu Condo - 9.9 miles away

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

Responds fast! Avg. 34 minutes

$327.00

Excellent (1 reviews)

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from $327.00 / night

1 / 9

Hauula House - 18 miles away

  • 3
  • 8
  • min stay varies
  • Child friendly

$217.00

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from $217.00 / night

(1)

1 / 26

Hauula House - 19 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Air conditioning

$274.00

Excellent (1 reviews)

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from $274.00 / night

(3)

1 / 18

Honolulu Condo - 9.7 miles away

  • 1
  • 2
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 34 minutes

$65.00

Excellent (3 reviews)

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from $65.00 / night

1 / 22

Hauula House - 18.3 miles away

  • 2
  • 5
  • min stay varies
  • Child friendly
  • Private garden

$178.00

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from $178.00 / night

1 / 31

Waimanalo House - 6.5 miles away

  • 6
  • 16
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$2,296.00

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from $2,296.00 / night

(36)

1 / 12

Honolulu Apartment - 9.8 miles away

  • 1
  • 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

Responds fast! Avg. 3 hours 24 minutes

$143.00

Excellent (36 reviews)

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from $143.00 / night

1 / 22

Hawaii Kai House - 7.7 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly

$1,075.00

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from $1,075.00 / night

1 / 30

Kahala Apartment - 8.5 miles away

  • 6
  • 11
  • 7 nights min
  • Child friendly

$2,500.00

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from $2,500.00 / night