50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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69 Vacation rentals

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7

Vacation studio in Kailua

Oahu / Kailua

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Kailua beach is about 1 mile from Kailua town. Kailua Guesthouse is located half-way between. It's about a 10-minute walk to the beach, a 10-minute walk to town. TheBus stop is about 300 feet from our front gate. My father acquired the property in 1947  …see more

from $139 / night

$910 / week

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from $139 / 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

23

Oahu / Kailua

2 6 3 nights min

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

 …see more

from $134 / night

$909 - $2579 / week

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from $134 / night

13

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $159 / night

$1113 / week

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from $159 / 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

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

24

Oahu / Kailua

Studio 16 7 nights min

  • Studio
  • 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

(14) Excellent 

34

Oahu / Kailua

1 2 3 nights min

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

 …see more

from $126 / night

$840 / week

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from $126 / night

15

Oahu / Kailua

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Air conditioning

 …see more

from $195 / night

$1365 / week

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from $195 / night

(2) Excellent 

13

Oahu / Kailua

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi

 …see more

from $350 / night

$2450 - $3850 / week

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from $350 / night

25

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $1650 / night

$11550 / week

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from $1650 / night

11

Oahu / Kailua

2 4 Min stay varies

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

 …see more

from $495 / night

$3465 / week

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from $495 / night

24

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $595 / night

$4165 / week

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from $595 / night

30

Oahu / Kailua

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $1500 / night

$10500 / week

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from $1500 / night

(1) Excellent 

19

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $155 / night

$1085 / week

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from $155 / night

(1) Very Good 

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

(7) Excellent 

23

Oahu / Kailua

2 4 5 nights min

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

 …see more

from $250 / night

$1600 / week

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from $250 / 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

16

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $550 / night

$3850 / week

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from $550 / 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 / week

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from $165 / night

14

Oahu / Kailua

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Child friendly

 …see more

from $225 / night

$1575 / week

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from $225 / night

24

Oahu / Kailua

3 7 Min stay varies

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

 …see more

from $350 / night

$2275 - $2660 / week

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from $350 / night

(3) Very Good 

23

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi

 …see more

from $450 / night

$3150 / week

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from $450 / 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

(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

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

28

Oahu / Kailua

3 8 Min stay varies

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

 …see more

from $700 / night

$4900 / week

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from $700 / night

33

Oahu / Kailua

5 12 Min stay varies

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

 …see more

from $1500 / night

$10500 / week

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from $1500 / night

20

Oahu / Kailua

6 12 10 nights min

  • 6 bedrooms
  • Sleeps 12
  • 10 nights min
  • Child friendly

 …see more

from $1050 / night

$7350 - $12250 / week

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from $1050 / 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

44

Oahu / Kailua

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly

 …see more

from $8000 / night

$56000 / week

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from $8000 / night

22

Oahu / Kailua

Studio 2 30 nights min

  • Studio
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+

 …see more

from $135 / night

$945 / week

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from $135 / night

40

Oahu / Kailua

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $2500 / night

$17500 - $35000 / week

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from $2500 / 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

35

Oahu / Kailua

4 8 10 nights min

  • 4 bedrooms
  • Sleeps 8
  • 10 nights min
  • Swimming pool
  • Child friendly

 …see more

from $3000 / night

$21000 / week

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from $3000 / night

(25) Very Good 

15

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Swimming pool

 …see more

from $105 / night

$730 / week

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from $105 / 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

7

Oahu / Kailua

9 20 6 nights min

  • 9 bedrooms
  • Sleeps 20
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $1135 / night

$7945 / week

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from $1135 / night

13

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min

 …see more

from $179 / night

$1200 / week

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from $179 / night

20

Oahu / Kailua

4 11 Min stay varies

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

 …see more

from $585 / night

$4095 / week

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from $585 / night