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Vacation Rentals
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Kailua
Studio /
1
BA /
Sleeps
2
From $140/nt
Featured
4
BR /
2
BA /
Sleeps
8
Featured
3
BR /
2
BA /
Sleeps
8
From $529/nt
Featured
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BR /
3
BA /
Sleeps
9
From $800/nt
Featured
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BR /
1
BA /
Sleeps
8
From $250/nt
Featured
Kailua with Pools
(113)
sort by
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Availability Last Updated
Accepts Online Payments
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Bedrooms: Most to Least
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Price: Low to High
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Special Offers First
Summer Decadence! - luxuriate in elegant and private home -pool, walk to beach
4 Bedrooms,
3
Bathrooms
, Sleeps 9
$800
per night
Summer Decadence! - luxuriate in elegant and private home -pool, walk to beach
Book it Now!
2 night Minimum Stay
4
BR,
3
BA,
Sleeps
9
Oahu
>
Kailua House
#236104
(13)
Compare
'Hale Nalu Palekaiko ' Pool, Walk to Kailua Beach
4 Bedrooms,
3
Bathrooms
, Sleeps 10
$425
per night
'Hale Nalu Palekaiko ' Pool, Walk to Kailua Beach
5 night Minimum Stay
4
BR,
3
BA,
Sleeps
10
Oahu
>
Kailua House
#65043vb
(32)
Compare
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach
1 Bedrooms,
1
Bathroom
, Sleeps 2
$175
per night
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach
Book it Now!
1
BR,
1
BA,
Sleeps
2
Oahu
>
Kailua Cottage
#241024
(12)
Compare
Place in Paradise - Beach Front; CANCELLATION MAY17-29 SPECIAL RATE OFFER!
5 Bedrooms,
5
Bathrooms
,
1
Half Bath
, Sleeps 14
$1,200 - $1,800
per night
Place in Paradise - Beach Front; CANCELLATION MAY17-29 SPECIAL RATE OFFER!
5 - 10 night Minimum Stay
5
BR,
5
BA,
1
HF BA,
Sleeps
14
Oahu
>
Kailua House
#10118vb
(6)
Compare
Stunning Kailua Oceanfront House with Beach Walk Right Outside
3 Bedrooms,
3
Bathrooms
, Sleeps 6
$4,550 - $7,700
per week
Stunning Kailua Oceanfront House with Beach Walk Right Outside
7 night Minimum Stay
3
BR,
3
BA,
Sleeps
6
Oahu
>
Kailua House
#221336
(36)
Compare
Akialoa Getaway: Large Studio Suite with wrap around balcony And AC!
1 Bedrooms,
1
Bathroom
, Sleeps 4
$175
per night
Akialoa Getaway: Large Studio Suite with wrap around balcony And AC!
3 night Minimum Stay
1
BR,
1
BA,
Sleeps
4
Oahu
>
Kailua House
#436652vb
(4)
Compare
Gracious Island Getaway on Beautiful Kailua Beach
4 Bedrooms, Sleeps 8
Gracious Island Getaway on Beautiful Kailua Beach
4
BR,
Sleeps
8
Oahu
>
Kailua House
#444417vb
(15)
Compare
Ka'hela - Paradise for Rent
4 Bedrooms,
4
Bathrooms
, Sleeps 8
Ka'hela - Paradise for Rent
4
BR,
4
BA,
Sleeps
8
Oahu
>
Kailua House
#3000795
1 Review
Compare
Kolea Estate-Gated Kailua Retreat! 1 Mile from Lanikai Beach
6 Bedrooms,
4
Bathrooms
,
1
Half Bath
, Sleeps 16
$1,000
per night
Kolea Estate-Gated Kailua Retreat! 1 Mile from Lanikai Beach
5 - 12 night Minimum Stay
6
BR,
4
BA,
1
HF BA,
Sleeps
16
Oahu
>
Kailua Villa
#384067
(30)
Compare
Sandcastle - Peaceful Beach House
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$45,000
per month
Sandcastle - Peaceful Beach House
30 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Oahu
>
Kailua House
#3524855
Compare
Stop! Must See Kailua Beachside Villa
4 Bedrooms,
4
Bathrooms
, Sleeps 8
$900
per night
Stop! Must See Kailua Beachside Villa
7 night Minimum Stay
4
BR,
4
BA,
Sleeps
8
Oahu
>
Kailua House
#337362
(4)
Compare
Charming & Spacious Kama'aina Home on Kailua Beach
3 Bedrooms,
3
Bathrooms
, Sleeps 8
Charming & Spacious Kama'aina Home on Kailua Beach
3
BR,
3
BA,
Sleeps
8
Oahu
>
Kailua House
#25474vb
(8)
Compare
Gorgeous 'Green' Executive Home on a Quiet Beach Lane
5 Bedrooms,
2
Bathrooms
,
1
Half Bath
, Sleeps 12
Gorgeous 'Green' Executive Home on a Quiet Beach Lane
5
BR,
2
BA,
1
HF BA,
Sleeps
12
Oahu
>
Kailua House
#317921
(10)
Compare
'Star of Hawaii' - Family Living, Pool, Walk to Beach
4 Bedrooms,
3
Bathrooms
, Sleeps 12
'Star of Hawaii' - Family Living, Pool, Walk to Beach
4
BR,
3
BA,
Sleeps
12
Oahu
>
Kailua House
#48531vb
(28)
Compare
Luxury Kailua Beachfront Estate in Kailua
5 Bedrooms,
5
Bathrooms
, Sleeps 10
Luxury Kailua Beachfront Estate in Kailua
5
BR,
5
BA,
Sleeps
10
Oahu
>
Kailua Villa
#288676
2 Reviews
Compare
Villa Lanikai Alii- Luxury Beachfront w/Pool, Spacious Yard, More
5 Bedrooms,
4
Bathrooms
, Sleeps 10
Villa Lanikai Alii- Luxury Beachfront w/Pool, Spacious Yard, More
5
BR,
4
BA,
Sleeps
10
Oahu
>
Kailua Villa
#3246731
Compare
Stop! Swimming Pool and its Across from the Beach.
4 Bedrooms,
2
Bathrooms
, Sleeps 8
Stop! Swimming Pool and its Across from the Beach.
4
BR,
2
BA,
Sleeps
8
Oahu
>
Kailua House
#249119vb
1 Review
Compare
Sleeps 10 - Salt Water Pool And Steps From Kailua Beach
5 Bedrooms,
3
Bathrooms
, Sleeps 10
Sleeps 10 - Salt Water Pool And Steps From Kailua Beach
5
BR,
3
BA,
Sleeps
10
Oahu
>
Kailua House
#445708vb
Compare
Bali-Hawaii Home 2,000 Sq.Feet with Private Pool
1 Bedrooms, Sleeps 5
$2,100
per week
Bali-Hawaii Home 2,000 Sq.Feet with Private Pool
Book it Now!
7 night Minimum Stay
1
BR,
Sleeps
5
Oahu
>
Kailua House
#220874vb
(12)
Compare
Families Reconnect Play Relax Together - Pool, Hot Tub, Short Walk to the Beach
3 Bedrooms,
2
Bathrooms
, Sleeps 8
$529
per night
Families Reconnect Play Relax Together - Pool, Hot Tub, Short Walk to the Beach
5 night Minimum Stay
3
BR,
2
BA,
Sleeps
8
Oahu
>
Kailua House
#207816
(48)
Compare
Akialoa Getaways- Huge 2bedroom Suite Living,Dining and Kitchen!
2 Bedrooms,
1
Bathroom
, Sleeps 4
$200
per night
Akialoa Getaways- Huge 2bedroom Suite Living,Dining and Kitchen!
3 night Minimum Stay
2
BR,
1
BA,
Sleeps
4
Oahu
>
Kailua House
#439113vb
(5)
Compare
Location! Quiet, Private Hawaiian Beachside Home w/ solar heated pool
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$5,250
per week
Location! Quiet, Private Hawaiian Beachside Home w/ solar heated pool
7 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Oahu
>
Kailua House
#266648
1 Review
Compare
Beach side Executive Home
4 Bedrooms,
3
Bathrooms
, Sleeps 8
$575
per night
Beach side Executive Home
5 night Minimum Stay
4
BR,
3
BA,
Sleeps
8
Oahu
>
Kailua House
#350477
(9)
Compare
Kailua Beachfront Retreat
6 Bedrooms,
5
Bathrooms
, Sleeps 10
Kailua Beachfront Retreat
6
BR,
5
BA,
Sleeps
10
Oahu
>
Kailua House
#206463
(6)
Compare
Your Island Home Away from Home!
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Your Island Home Away from Home!
3
BR,
2
BA,
Sleeps
8
Oahu
>
Kailua House
#313988
(34)
Compare
Beautiful Villa On Kailua Beachside
6 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 14
Beautiful Villa On Kailua Beachside
6
BR,
3
BA,
1
HF BA,
Sleeps
14
Oahu
>
Kailua House
#469879vb
Compare
Tropical Hideaway Studio on the Water in Kailua with Swimming Pool
Studio,
1
Bathroom
, Sleeps 4
$149 - $155
per night
Tropical Hideaway Studio on the Water in Kailua with Swimming Pool
Book it Now!
2 night Minimum Stay
Studio,
1
BA,
Sleeps
4
Oahu
>
Kailua Studio
#913424
(25)
Compare
Aloha from the Island of Oahu, and Welcome to Paradise!
5 Bedrooms,
4
Bathrooms
, Sleeps 16
$600 - $650
per night
Aloha from the Island of Oahu, and Welcome to Paradise!
5 - 7 night Minimum Stay
5
BR,
4
BA,
Sleeps
16
Oahu
>
Kailua House
#42225vb
(24)
Compare
Stunning Kailua Beachside 3 BR Home with Lagoon Pool
3 Bedrooms,
2
Bathrooms
, Sleeps 8
Stunning Kailua Beachside 3 BR Home with Lagoon Pool
3
BR,
2
BA,
Sleeps
8
Oahu
>
Kailua House
#317922
(5)
Compare
Kailua Executive Estate Resort Living
4 Bedrooms,
3
Bathrooms
,
1
Half Bath
, Sleeps 10
$7,700 - $8,080
per week
Kailua Executive Estate Resort Living
7 night Minimum Stay
4
BR,
3
BA,
1
HF BA,
Sleeps
10
Oahu
>
Kailua Estate
#446284vb
1 Review
Compare
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