50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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65 Vacation rentals

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 and b …see more

from $140 / night

$911 / week

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from $140 / night

(8) 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

from $251 / night

$1600 / week

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from $251 / night

(2) Excellent 

12

Oahu / Kailua

1 2 1 night min

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

from $180 / night

$1254 / week

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from $180 / 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

from $353 / night

$2470 - $3881 / week

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from $353 / night

23

Oahu / Kailua

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from $120 / night

$808 - $1968 / week

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from $120 / 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

from $131 / night

$911 / week

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from $131 / night

24

Oahu / Kailua

1 2 7 nights min

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

from $151 / night

$1051 / week

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from $151 / night

28

Oahu / Kailua

3 8 Min stay varies

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

from $651 / night

$4551 / week

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from $651 / night

30

Oahu / Kailua

6 14 Min stay varies

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

from $1500 / night

$10500 / week

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from $1500 / 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

from $451 / night

$3151 / week

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from $451 / night

13

Oahu / Kailua

1 3 Min stay varies

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

from $160 / night

$1114 / week

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from $160 / night

15

Oahu / Kailua

1 3 3 nights min

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

from $196 / night

$1365 / week

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from $196 / night

21

Oahu / Kailua

3 8 30 nights min

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

from $600 / night

$4200 / week

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from $600 / night

(1) Very Good 

8

Oahu / Kailua

2 4 5 nights min

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

from $351 / night

$2451 / week

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from $351 / night

14

Oahu / Kailua

1 5 3 nights min

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

from $225 / night

$1575 / week

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from $225 / night

20

Oahu / Kailua

4 11 Min stay varies

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

from $585 / night

$4095 / week

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from $585 / night

16

Oahu / Kailua

3 6 Min stay varies

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

from $551 / night

$3851 / week

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from $551 / night

(16) Excellent 

34

Oahu / Kailua

1 2 3 nights min

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

from $127 / night

$840 / week

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from $127 / night

35

Oahu / Kailua

4 8 Min stay varies

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

from $2896 / night

$20266 / week

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from $2896 / 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

from $67 / night

$451 / week

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from $67 / night

(4) Excellent 

16

Oahu / Kailua

1 2 5 nights min

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

from $191 / night

$1300 / week

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from $191 / night

53

Oahu / Kailua

8 16 7 nights min

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

from $7000 / night

$49000 / week

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from $7000 / 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

from $156 / night

$1086 / week

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from $156 / night

(3) Very Good 

30

Oahu / Kailua

4 7 5 nights min

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

from $351 / night

$2451 / week

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from $351 / night

(2) Very Good 

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

from $165 / night

$1085 / week

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from $165 / 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

from $145 / night

$951 / week

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from $145 / night

24

Oahu / Kailua

3 6 Min stay varies

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

from $596 / night

$4166 / week

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from $596 / night

17

Oahu / Kailua

6 12 14 nights min

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

from $1051 / night

$12251 / week

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from $1051 / night

23

Oahu / Kailua

4 10 Min stay varies

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

from $1020 / night

$7140 / week

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from $1020 / night

25

Oahu / Kailua

4 10 Min stay varies

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

from $1500 / night

$10500 / week

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from $1500 / night

(25) Very Good 

19

Oahu / Kailua

1 2 5 nights min

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

from $105 / night

$731 / week

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from $105 / night

30

Oahu / Kailua

3 6 14 nights min

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

from $425 / night

$2975 / week

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from $425 / night

20

Oahu / Kailua

5 10 5 nights min

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

from $900 / night

$6300 - $9800 / week

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from $900 / night

10

Oahu / Kailua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

from $200 / night

$1394 / week

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from $200 / night

27

Oahu / Kailua

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

from $7000 / night

$49000 - $87500 / week

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from $7000 / night

(1) Very Good 

6

Oahu / Kailua

3 6 Min stay varies

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

from $976 / night

$6825 / week

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from $976 / night

23

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min

from $160 / night

$1120 / week

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from $160 / 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

from $200 / night

$1400 / week

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from $200 / night

24

Oahu / Kailua

1 3 5 nights min

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

from $151 / night

$1200 / week

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from $151 / 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

from $91 / night

$565 / week

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from $91 / night

1