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Holiday Rentals in Kailua

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273 rentals in Kailua.
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Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, holiday rental in Kailua
Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, holiday rental in Kailua
Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, holiday rental in Kailua

Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, holiday rental in Kailua
SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, holiday rental in Kailua
SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, holiday rental in Kailua

SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10), holiday rental in Kailua
Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10), holiday rental in Kailua
Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10), holiday rental in Kailua

Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10)

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Kailua Beachfront - Licensed Rental #90/TVU-0248, holiday rental in Kailua
Kailua Beachfront - Licensed Rental #90/TVU-0248, holiday rental in Kailua
Kailua Beachfront - Licensed Rental #90/TVU-0248, holiday rental in Kailua

Kailua Beachfront - Licensed Rental #90/TVU-0248

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, holiday rental in Kailua
'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, holiday rental in Kailua
'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, holiday rental in Kailua

'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, holiday rental in Kailua
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, holiday rental in Kailua
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, holiday rental in Kailua

'Koi Palms Luxury Cottage' Short Walk to Kailua Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Adorable Beachfront Home with Gorgeous Ocean Views, holiday rental in Kailua
Adorable Beachfront Home with Gorgeous Ocean Views, holiday rental in Kailua
Adorable Beachfront Home with Gorgeous Ocean Views, holiday rental in Kailua

Adorable Beachfront Home with Gorgeous Ocean Views

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lanikai Ocean Front; Licensed Short Term Rental: #90/TVU-0042, holiday rental in Kailua
Lanikai Ocean Front; Licensed Short Term Rental: #90/TVU-0042, holiday rental in Kailua
Lanikai Ocean Front; Licensed Short Term Rental: #90/TVU-0042, holiday rental in Kailua

Lanikai Ocean Front; Licensed Short Term Rental: #90/TVU-0042

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Walk to beach, 3 bd, 2 bth private house,  heated pool, yard, AC, WIFI, parking, holiday rental in Kailua
Walk to beach, 3 bd, 2 bth private house,  heated pool, yard, AC, WIFI, parking, holiday rental in Kailua
Walk to beach, 3 bd, 2 bth private house,  heated pool, yard, AC, WIFI, parking, holiday rental in Kailua

Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lanikai Cottage on Secluded Quiet Beach with Amazing Views, holiday rental in Kailua
Lanikai Cottage on Secluded Quiet Beach with Amazing Views, holiday rental in Kailua
Lanikai Cottage on Secluded Quiet Beach with Amazing Views, holiday rental in Kailua

Lanikai Cottage on Secluded Quiet Beach with Amazing Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enchanting Beach Bungalow with Private Garden, holiday rental in Kailua
Enchanting Beach Bungalow with Private Garden, holiday rental in Kailua
Enchanting Beach Bungalow with Private Garden, holiday rental in Kailua

Enchanting Beach Bungalow with Private Garden

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability, holiday rental in Kailua
Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability, holiday rental in Kailua
Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability, holiday rental in Kailua

Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, holiday rental in Kailua
Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, holiday rental in Kailua
Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, holiday rental in Kailua

Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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The Perfect Kailua Retreat!, holiday rental in Kailua
The Perfect Kailua Retreat!, holiday rental in Kailua
The Perfect Kailua Retreat!, holiday rental in Kailua

The Perfect Kailua Retreat!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Pristine Cozy 1000 sqf 1 bdrm aprt With Sweeping Views of Kailua, holiday rental in Kailua
Pristine Cozy 1000 sqf 1 bdrm aprt With Sweeping Views of Kailua, holiday rental in Kailua
Pristine Cozy 1000 sqf 1 bdrm aprt With Sweeping Views of Kailua, holiday rental in Kailua

Pristine Cozy 1000 sqf 1 bdrm aprt With Sweeping Views of Kailua

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kailua Beach Vacation Cottage, holiday rental in Kailua
Kailua Beach Vacation Cottage, holiday rental in Kailua
Kailua Beach Vacation Cottage, holiday rental in Kailua

Kailua Beach Vacation Cottage

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Barefoot living on Lanikai Beach -- BEACHFRONT!, holiday rental in Kailua
Barefoot living on Lanikai Beach -- BEACHFRONT!, holiday rental in Kailua
Barefoot living on Lanikai Beach -- BEACHFRONT!, holiday rental in Kailua

Barefoot living on Lanikai Beach -- BEACHFRONT!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, holiday rental in Kailua
Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, holiday rental in Kailua
Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, holiday rental in Kailua

Awesome Beachside Cottage Located Just Steps Away from Kailua Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Just off the Sand-Heated Pool-Air Conditioned-Quiet/Secure-Ask Owner/rates&dates, holiday rental in Kailua
Just off the Sand-Heated Pool-Air Conditioned-Quiet/Secure-Ask Owner/rates&dates, holiday rental in Kailua
Just off the Sand-Heated Pool-Air Conditioned-Quiet/Secure-Ask Owner/rates&dates, holiday rental in Kailua

Just off the Sand-Heated Pool-Air Conditioned-Quiet/Secure-Ask Owner/rates&dates

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, holiday rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, holiday rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, holiday rental in Kailua

10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Stunning Kailua Oceanfront House, holiday rental in Kailua
Stunning Kailua Oceanfront House, holiday rental in Kailua
Stunning Kailua Oceanfront House, holiday rental in Kailua

Stunning Kailua Oceanfront House

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, holiday rental in Kailua
Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, holiday rental in Kailua
Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, holiday rental in Kailua

Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, holiday rental in Kailua
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, holiday rental in Kailua
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, holiday rental in Kailua

Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Come Relax on the Lake! Kayaks and SUP included!!!, holiday rental in Kailua
Come Relax on the Lake! Kayaks and SUP included!!!, holiday rental in Kailua
Come Relax on the Lake! Kayaks and SUP included!!!, holiday rental in Kailua

Come Relax on the Lake! Kayaks and SUP included!!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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42 feet from Beautiful White Sands and Kailua Beach, holiday rental in Kailua
42 feet from Beautiful White Sands and Kailua Beach, holiday rental in Kailua
42 feet from Beautiful White Sands and Kailua Beach, holiday rental in Kailua

42 feet from Beautiful White Sands and Kailua Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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KAILUA-STEPS TO THE BEACH, holiday rental in Kailua
KAILUA-STEPS TO THE BEACH, holiday rental in Kailua
KAILUA-STEPS TO THE BEACH, holiday rental in Kailua

KAILUA-STEPS TO THE BEACH

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, holiday rental in Kailua
Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, holiday rental in Kailua
Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, holiday rental in Kailua

Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, holiday rental in Kailua
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, holiday rental in Kailua
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, holiday rental in Kailua

Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, holiday rental in Kailua
Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, holiday rental in Kailua
Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, holiday rental in Kailua

Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, holiday rental in Kailua
Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, holiday rental in Kailua
Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, holiday rental in Kailua

Bring your aloha shirt and visit Kailua TAX I.D.W********-01 NUC 90/BB-0069

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Prime Location Across from Kailua Beach Park w/AC!!, holiday rental in Kailua
Prime Location Across from Kailua Beach Park w/AC!!, holiday rental in Kailua
Prime Location Across from Kailua Beach Park w/AC!!, holiday rental in Kailua

Prime Location Across from Kailua Beach Park w/AC!!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Spacious 3 story home with unbelievable views & access to secluded beach!, holiday rental in Kailua
Spacious 3 story home with unbelievable views & access to secluded beach!, holiday rental in Kailua
Spacious 3 story home with unbelievable views & access to secluded beach!, holiday rental in Kailua

Spacious 3 story home with unbelievable views & access to secluded beach!

Holiday Rental House
6 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
More info
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Happy House on Exquisite Kailua Beachside Property!, holiday rental in Kailua
Happy House on Exquisite Kailua Beachside Property!, holiday rental in Kailua
Happy House on Exquisite Kailua Beachside Property!, holiday rental in Kailua

Happy House on Exquisite Kailua Beachside Property!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., holiday rental in Kailua
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., holiday rental in Kailua
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., holiday rental in Kailua

Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tradewind Bungalow, in Kailua on Oahu, holiday rental in Kailua
Tradewind Bungalow, in Kailua on Oahu, holiday rental in Kailua
Tradewind Bungalow, in Kailua on Oahu, holiday rental in Kailua

Tradewind Bungalow, in Kailua on Oahu

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, holiday rental in Kailua
Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, holiday rental in Kailua
Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, holiday rental in Kailua

Great Location, Large Pool, Koi Pond, Walk to Kailua Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
More info
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Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, holiday rental in Kailua
Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, holiday rental in Kailua
Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, holiday rental in Kailua

Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Single-Family Home on large tropical landscaped lot, holiday rental in Kailua
Private Single-Family Home on large tropical landscaped lot, holiday rental in Kailua
Private Single-Family Home on large tropical landscaped lot, holiday rental in Kailua

Private Single-Family Home on large tropical landscaped lot

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, holiday rental in Kailua
Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, holiday rental in Kailua
Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, holiday rental in Kailua

Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Steps to the Beach Guesthouse, holiday rental in Kailua
Steps to the Beach Guesthouse, holiday rental in Kailua
Steps to the Beach Guesthouse, holiday rental in Kailua

Steps to the Beach Guesthouse

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Resort-like, Kailua Lanikai, 2 Min/Beach, AC, WiFi, Pool, Kayaks, MAY SPECIAL!, holiday rental in Kailua
Resort-like, Kailua Lanikai, 2 Min/Beach, AC, WiFi, Pool, Kayaks, MAY SPECIAL!, holiday rental in Kailua
Resort-like, Kailua Lanikai, 2 Min/Beach, AC, WiFi, Pool, Kayaks, MAY SPECIAL!, holiday rental in Kailua

Resort-like, Kailua Lanikai, 2 Min/Beach, AC, WiFi, Pool, Kayaks, MAY SPECIAL!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
More info
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5 Minute Walk to Kailua Beach, holiday rental in Kailua
5 Minute Walk to Kailua Beach, holiday rental in Kailua
5 Minute Walk to Kailua Beach, holiday rental in Kailua

5 Minute Walk to Kailua Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Close  to beach, sleeps 2, AC, quiet, private, holiday rental in Kailua
Close  to beach, sleeps 2, AC, quiet, private, holiday rental in Kailua
Close  to beach, sleeps 2, AC, quiet, private, holiday rental in Kailua

Close to beach, sleeps 2, AC, quiet, private

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Canal-font, lovely renovated home, 10 min walk to the beach., holiday rental in Kailua
Canal-font, lovely renovated home, 10 min walk to the beach., holiday rental in Kailua
Canal-font, lovely renovated home, 10 min walk to the beach., holiday rental in Kailua

Canal-font, lovely renovated home, 10 min walk to the beach.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Kahela - Paradise for Rent, holiday rental in Kailua
Kahela - Paradise for Rent, holiday rental in Kailua
Kahela - Paradise for Rent, holiday rental in Kailua

Kahela - Paradise for Rent

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous Views and Home. Minutes from Lanikai Beach in Kailua., holiday rental in Kailua
Gorgeous Views and Home. Minutes from Lanikai Beach in Kailua., holiday rental in Kailua
Gorgeous Views and Home. Minutes from Lanikai Beach in Kailua., holiday rental in Kailua

Gorgeous Views and Home. Minutes from Lanikai Beach in Kailua.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Beachfront Rental, holiday rental in Kailua
Private Beachfront Rental, holiday rental in Kailua
Private Beachfront Rental, holiday rental in Kailua

Private Beachfront Rental

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Nancy's Kailua Cottage Mauka, holiday rental in Kailua
Nancy's Kailua Cottage Mauka, holiday rental in Kailua
Nancy's Kailua Cottage Mauka, holiday rental in Kailua

Nancy's Kailua Cottage Mauka

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Payment Protection

Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot, holiday rental in Kailua
Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot, holiday rental in Kailua
Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot, holiday rental in Kailua

Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Kailua Beachfront w/direct beach access; Licensed Rental #90/TVU-0141, holiday rental in Kailua
Kailua Beachfront w/direct beach access; Licensed Rental #90/TVU-0141, holiday rental in Kailua
Kailua Beachfront w/direct beach access; Licensed Rental #90/TVU-0141, holiday rental in Kailua

Kailua Beachfront w/direct beach access; Licensed Rental #90/TVU-0141

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Frequently Asked Questions about Kailua