50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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72 Vacation rentals

Travelers going to Kailua are booking December dates now. Secure your vacation rental today and have the perfect trip.

(6) Excellent 

23

Oahu / Kailua

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $236 / night

$1650 - $1800 / week

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from $236 / night

(1) Excellent 

22

Oahu / Kailua

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Private garden

 …see more

from $199 / night

$1400 / week

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from $199 / night

(5) Excellent 

24

Oahu / Kailua

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Ask about children

 …see more

from $189 / night

$1323 / week

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from $189 / night

13

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Car not necessary

 …see more

from $159 / night

$1113 / week

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from $159 / night

(8) Excellent 

28

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $80 / night

$560 / week

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from $80 / night

8

Oahu / Kailua

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $66 / night

$450 / week

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from $66 / night

(1) Excellent 

25

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.18 mi
  • Ask about children

 …see more

from $165 / night

$1085 - $1225 / week

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from $165 / night

(2) Excellent 

12

Oahu / Kailua

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Private garden

 …see more

from $199 / night

$1500 / week

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from $199 / night

8

Oahu / Kailua

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly

 …see more

from $350 / night

$2450 / week

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from $350 / night

(1) Excellent 

19

Oahu / Kailua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $155 / night

$1085 / week

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from $155 / night

(2) Very Good 

30

Oahu / Kailua

4 7 5 nights min

  • 4 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $350 / night

$2450 / week

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from $350 / night

(12) Excellent 

34

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children

 …see more

from $126 / night

$840 / week

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from $126 / night

(3) Excellent 

16

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
  • Air conditioning

 …see more

from $190 / night

$1300 / week

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from $190 / night

38

Oahu / Kailua

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children

 …see more

from $6000 / night

$42000 - $70000 / week

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from $6000 / night

6

Oahu / Kailua

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $90 / night

$565 / week

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from $90 / night

12

Oahu / Kailua

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $130 / night

$910 / week

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from $130 / night

(1) Excellent 

12

Oahu / Kailua

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $145 / night

$950 / week

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from $145 / night

38

Oahu / Kailua

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $6250 / night

$43750 - $65625 / week

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from $6250 / night

24

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $100 / night

$700 - $933 / week

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from $100 / night

9

Oahu / Kailua

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly

 …see more

from $260 / night

$1820 / week

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from $260 / night

5

Oahu / Kailua

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Air conditioning
  • Pet friendly

 …see more

from $206 / night

$1442 - $1862 / week

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from $206 / night

12

Oahu / Kailua

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $495 / night

$3465 - $5075 / week

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from $495 / night

16

Oahu / Kailua

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $148 / night

$999 / week

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from $148 / night

21

Oahu / Kailua

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi

 …see more

from $600 / night

$4200 / week

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from $600 / night

7

Oahu / Kailua

9 20 Min stay varies

  • 9 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $1135 / night

$7945 / week

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from $1135 / night

26

Oahu / Kailua

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $4500 / night

$31500 - $42000 / week

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from $4500 / night

(3) Excellent 

21

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Air conditioning

 …see more

from $200 / night

$1400 / week

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from $200 / night

20

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min

 …see more

from $160 / night

$1120 / week

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from $160 / night

26

Oahu / Kailua

5 10 10 nights min

  • 5 bedrooms
  • Sleeps 10
  • 10 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $1200 / night

$8400 - $17500 / week

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from $1200 / night

20

Oahu / Kailua

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $900 / night

$6300 - $9800 / week

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from $900 / night

37

Oahu / Kailua

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly

 …see more

from $7000 / night

$49000 - $87500 / week

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from $7000 / night

13

Oahu / Kailua

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+

 …see more

from $169 / night

$1183 / week

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from $169 / night

24

Oahu / Kailua

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Ask about children
  • Ask about pets

 …see more

from $7000 / night

$49000 - $87500 / week

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from $7000 / night

34

Oahu / Kailua

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

 …see more

from $1500 / night

$10500 - $15750 / week

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from $1500 / night

21

Oahu / Kailua

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly

 …see more

from $585 / night

$4095 - $7000 / week

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from $585 / night

8

Oahu / Kailua

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly

 …see more

from $600 / night

$4200 / week

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from $600 / night

17

Oahu / Kailua

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation

 …see more

from $1050 / night

$12250 / week

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from $1050 / night

23

Oahu / Kailua

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $750 / night

$5250 / week

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from $750 / night

29

Oahu / Kailua

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $575 / night

$4025 - $8575 / week

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from $575 / night

23

Oahu / Kailua

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $178 / night

$1246 / week

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from $178 / night

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