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Kailua Vacation Rentals

Kailua Waterfront Homes, Apartments & More - 212 Rentals Available.

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Air conditioning (13)
Balcony or terrace (4)
DVD player (19)
Dishwasher (19)
Fireplace (1)
Garden (2)
Grill (14)
Heated pool (2)
High Speed Internet (27)
High chair (1)
Hot tub/Jacuzzi (12)
Private pool (15)
Sauna (1)
Swimming pool (18)
Washing machine (19)
Wi-Fi available (18)

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Villa (6)

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212 Vacation rentals

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Filters applied: Waterfront

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

1 / 32

Ohana Beachfront Villa - luxury home w/ pool - ID

Kailua House

5 bedrooms 5
6 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$4,725.00

from $4,725.00 / night

Book

1 / 26

Absolutely Oceanfront Kailua Vacation Rental- $199

Kailua House

1 bedroom 1
1 bathroom
sleeps 3 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

$299.00

Very Good (4 reviews)

from $299.00 / night

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1 / 16

Kailua Surf Paradise Hale, pool

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 10 10
7 nights min

Swimming pool
Ask about children
Air conditioning

Responds fast! Avg. 1 hour 46 minutes

$550.00

from $550.00 / night

Book

1 / 12

Kailua Ocean View Studio 2 decks-Upgraded-60 foot pool w waterfalls-Wow! $199

Kailua House

1 bedroom 1
1 bathroom
sleeps 3 3
3 nights min

Swimming pool
Child friendly
Air conditioning

$299.00

from $299.00 / night

Book

1 / 17

Jungle Waterfall Retreat - w/ AC, BBQ

Kailua House

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Nearest beach 6 mi
Ask about children
Air conditioning

$330.00

from $330.00 / night

Book

1 / 59

Stunning Kailua Oceanfront Getaway

Kailua House

3 bedrooms 3
3 bathrooms
sleeps 6 6
6 nights min

Beach/lakeside relaxation
Swimming pool
Child friendly

$775.00

from $775.00 / night

Book

1 / 21

Shangri-La By The Sea - Tranquil, Gorgeous Stunning views with pool - ID

Kailua House

5 bedrooms 5
3 bathrooms
sleeps 10 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

$1,070.00

Very Good (1 reviews)

from $1,070.00 / night

Book

1 / 40

Unforgettable Beachfront Oasis

Kailua House

6 bedrooms 6
5 bathrooms
sleeps 12 12
7 nights min

Beach/lakeside relaxation
Swimming pool
Ask about children

“We rented this beautiful house for 10 days over Christmas, it was an absolutely wonderful vacation in a perfect home!! Wanda was an absolute sweetheart, thank you for all the wonderful gifts when we arrived!! I requested a Christmas tree because we...”

- Review left on 01/27/2016

$1,500.00

Very Good (8 reviews)

from $1,500.00 / night

Inquire

1 / 29

Oasis Villa - outdoor kitchen, pool and jacuzzi - ID

Kailua House

6 bedrooms 6
5 bathrooms
sleeps 18 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

$1,305.00

Very Good (1 reviews)

from $1,305.00 / night

Book

1 / 17

Lanikai Ohana Hale

Kailua House

1 bedroom 1
1 bathroom
sleeps 5 5
min stay varies

Child friendly

$225.00

from $225.00 / night

Inquire

1 / 30

Lanikai Cottage

Kailua House

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly

$455.00

from $455.00 / night

Inquire

1 / 44

Castle Point Estate

Kailua House

7 bedrooms 7
8 bathrooms
sleeps 15 15
min stay varies

Swimming pool
Child friendly

$9,500.00

from $9,500.00 / night

Inquire

1 / 26

Plantation at Paradise Point

Kailua Villa

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Ask about children
Ask about pets

Responds fast! Avg. 1 hour 49 minutes

$4,500.00

from $4,500.00 / night

Book

1 / 25

Kehaulani

Kailua Villa

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Ask about children
Ask about pets

Responds fast! Avg. 1 hour 49 minutes

$900.00

from $900.00 / night

Book

1 / 20

Premier Oceanfront Vacation Home

Kailua Villa

6 bedrooms 6
5 bathrooms
sleeps 12 12
min stay varies

Child friendly

Responds fast! Avg. 37 minutes

$1,050.00

from $1,050.00 / night

Book

1 / 24

Hale Nani Lanikai

Kailua House

3 bedrooms 3
4 bathrooms
sleeps 8 8
min stay varies

Child friendly

$695.00

from $695.00 / night

Inquire

1 / 28

Just steps to the beach with private pool. *Monthly rental**

Kailua House

6 bedrooms 6
6 bathrooms
sleeps 14 14
7 nights min

Swimming pool
Ask about children
Air conditioning

$1,050.00

from $1,050.00 / night

Inquire

1 / 25

Maluhia

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$1,500.00

from $1,500.00 / night

Inquire

1 / 37

Royal Kailua Estate

Kailua Villa

8 bedrooms 8
10 bathrooms
sleeps 16 16
7 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 37 minutes

$9,500.00

from $9,500.00 / night

Book

1 / 40

Kailani Villa

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Child friendly

$900.00

from $900.00 / night

Inquire

1 / 24

Ke'aloha

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 11 11
min stay varies

Child friendly

$480.00

from $480.00 / night

Inquire

1 / 37

Hale Mokulua

Kailua Villa

5 bedrooms 5
5 bathrooms
sleeps 14 14
min stay varies

Ask about children
Ask about pets

Responds fast! Avg. 1 hour 49 minutes

$1,500.00

from $1,500.00 / night

Book

1 / 26

Kailua Beach House

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly

$1,250.00

from $1,250.00 / night

Inquire

1 / 14

Hale Kimo

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly

$660.00

from $660.00 / night

Inquire

1 / 39

Stunning Estate Owned by Paul Mitchell on Lanikai Beach on Oahu!

Kailua Villa

7 bedrooms 7
7 bathrooms
sleeps 14 14
7 nights min

Swimming pool
Ask about children
Air conditioning

$6,000.00

from $6,000.00 / night

Inquire

1 / 35

Lanikai Plumeria Beach House

Kailua House

5 bedrooms 5
6 bathrooms
sleeps 12 12
min stay varies

Child friendly

$725.00

from $725.00 / night

Inquire

1 / 27

Lanikai Breeze

Kailua House

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly

$1,500.00

from $1,500.00 / night

Inquire

1 / 23

Lanikai Ocean View Villa

Kailua House

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly

$1,000.00

from $1,000.00 / night

Inquire

1 / 26

Lanikai Oceanside

Kailua House

4 bedrooms 4
4 bathrooms
sleeps 10 10
min stay varies

Child friendly
Air conditioning

$2,000.00

from $2,000.00 / night

Inquire

Page 1 of 6

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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.

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.

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