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Kailua Vacation Rentals

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250 rentals in Kailua.
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Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, vacation rental in Kailua
Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, vacation rental in Kailua
Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, vacation 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
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SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, vacation rental in Kailua
SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, vacation rental in Kailua
SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, vacation 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), vacation rental in Kailua
Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10), vacation rental in Kailua
Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10), vacation 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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Licensed Short Term Rental Beach Front - Kailua, vacation rental in Kailua
Licensed Short Term Rental Beach Front - Kailua, vacation rental in Kailua
Licensed Short Term Rental Beach Front - Kailua, vacation rental in Kailua

Licensed Short Term Rental Beach Front - Kailua

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, vacation rental in Kailua
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, vacation rental in Kailua
'Koi Palms Luxury Cottage' Short Walk to Kailua Beach, vacation 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, vacation rental in Kailua
Adorable Beachfront Home with Gorgeous Ocean Views, vacation rental in Kailua
Adorable Beachfront Home with Gorgeous Ocean Views, vacation 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 , near Buzz's Steakhouse, vacation rental in Kailua
Lanikai Ocean Front; Licensed Short Term Rental , near Buzz's Steakhouse, vacation rental in Kailua
Lanikai Ocean Front; Licensed Short Term Rental , near Buzz's Steakhouse, vacation rental in Kailua

Lanikai Ocean Front; Licensed Short Term Rental , near Buzz's Steakhouse

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lanikai Cottage on Secluded Quiet Beach with Amazing Views, vacation rental in Kailua
Lanikai Cottage on Secluded Quiet Beach with Amazing Views, vacation rental in Kailua
Lanikai Cottage on Secluded Quiet Beach with Amazing Views, vacation 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, vacation rental in Kailua
Enchanting Beach Bungalow with Private Garden, vacation rental in Kailua
Enchanting Beach Bungalow with Private Garden, vacation rental in Kailua

Enchanting Beach Bungalow with Private Garden

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, vacation rental in Kailua
Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, vacation rental in Kailua
Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, vacation rental in Kailua

Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c

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, vacation rental in Kailua
Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability, vacation rental in Kailua
Steps to Kailua Beach-Heated Pool-Air Conditioned-Ask Owner Availability, vacation 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, vacation rental in Kailua
Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, vacation rental in Kailua
Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, vacation 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!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Oasis, Steps To The Beach! 100% Solar!, vacation rental in Kailua
Perfect Oasis, Steps To The Beach! 100% Solar!, vacation rental in Kailua
Perfect Oasis, Steps To The Beach! 100% Solar!, vacation rental in Kailua

Perfect Oasis, Steps To The Beach! 100% Solar!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kailua Beach Vacation Cottage, vacation rental in Kailua
Kailua Beach Vacation Cottage, vacation rental in Kailua
Kailua Beach Vacation Cottage, vacation rental in Kailua

Kailua Beach Vacation Cottage

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

Barefoot living on Lanikai Beach -- BEACHFRONT!

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

Stunning Kailua Oceanfront House

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, vacation rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, vacation rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/private pool/solar, vacation rental in Kailua

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, vacation rental in Kailua
Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, vacation rental in Kailua
Steps to Paradise - Kailua Beachside - Daily or Discounted Monthly Rates, vacation rental in Kailua

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Best Price and Location on Beautiful Kailua Beach!, vacation rental in Kailua
Best Price and Location on Beautiful Kailua Beach!, vacation rental in Kailua
Best Price and Location on Beautiful Kailua Beach!, vacation rental in Kailua

Best Price and Location on Beautiful Kailua Beach!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spend September and October 42 feet from Beautiful Kailua Beach, vacation rental in Kailua
Spend September and October 42 feet from Beautiful Kailua Beach, vacation rental in Kailua
Spend September and October 42 feet from Beautiful Kailua Beach, vacation rental in Kailua

Spend September and October 42 feet from Beautiful Kailua Beach

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, vacation rental in Kailua
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, vacation rental in Kailua
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option, vacation 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
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KAILUA-STEPS TO THE BEACH, vacation rental in Kailua
KAILUA-STEPS TO THE BEACH, vacation rental in Kailua
KAILUA-STEPS TO THE BEACH, vacation rental in Kailua

KAILUA-STEPS TO THE BEACH

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, vacation rental in Kailua
Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, vacation rental in Kailua
Kailua Lanikai By The Sea- 3 Bed, 2 1/2 Baths, 2200 sq. ft., A/C, Sleeps, vacation 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
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Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, vacation rental in Kailua
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, vacation rental in Kailua
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry, vacation 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
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Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, vacation rental in Kailua
Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, vacation rental in Kailua
Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!, vacation 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
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Footsteps to Hawaii's Best Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, vacation rental in Kailua
Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, vacation rental in Kailua
Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, vacation 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
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Prime Location Across from Kailua Beach Park w/AC!!, vacation rental in Kailua
Prime Location Across from Kailua Beach Park w/AC!!, vacation rental in Kailua
Prime Location Across from Kailua Beach Park w/AC!!, vacation rental in Kailua

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Happy House on Exquisite Kailua Beachside Property!, vacation rental in Kailua
Happy House on Exquisite Kailua Beachside Property!, vacation rental in Kailua
Happy House on Exquisite Kailua Beachside Property!, vacation rental in Kailua

Happy House on Exquisite Kailua Beachside Property!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., vacation rental in Kailua
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., vacation rental in Kailua
Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., vacation 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
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Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, vacation rental in Kailua
Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, vacation rental in Kailua
Great Location, Large Pool, Koi Pond, Walk to Kailua Beach, vacation rental in Kailua

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, vacation rental in Kailua
Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, vacation rental in Kailua
Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach, vacation 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
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30 day minimum, vacation rental in Kailua
30 day minimum, vacation rental in Kailua
30 day minimum, vacation rental in Kailua

30 day minimum

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, vacation rental in Kailua
Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, vacation rental in Kailua
Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, vacation 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
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Resort-like, Kailua-Lanikai, 2 Min/Beach, AC, WiFi, Pool/Hot tub, Kayaks, vacation rental in Kailua
Resort-like, Kailua-Lanikai, 2 Min/Beach, AC, WiFi, Pool/Hot tub, Kayaks, vacation rental in Kailua
Resort-like, Kailua-Lanikai, 2 Min/Beach, AC, WiFi, Pool/Hot tub, Kayaks, vacation rental in Kailua

Resort-like, Kailua-Lanikai, 2 Min/Beach, AC, WiFi, Pool/Hot tub, Kayaks

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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5 Minute Walk to Kailua Beach, vacation rental in Kailua
5 Minute Walk to Kailua Beach, vacation rental in Kailua
5 Minute Walk to Kailua Beach, vacation rental in Kailua

5 Minute Walk to Kailua Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Canal-font, lovely renovated home, 10 min walk to the beach., vacation rental in Kailua
Canal-font, lovely renovated home, 10 min walk to the beach., vacation rental in Kailua
Canal-font, lovely renovated home, 10 min walk to the beach., vacation 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
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Kahela - Paradise for Rent, vacation rental in Kailua
Kahela - Paradise for Rent, vacation rental in Kailua
Kahela - Paradise for Rent, vacation rental in Kailua

Kahela - Paradise for Rent

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

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot Tu, vacation rental in Kailua
Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot Tu, vacation rental in Kailua
Palione Papalani by AvantStay | Steps from Kailua Beach w/ Private Pool & Hot Tu, vacation rental in Kailua

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

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Kailua Beachfront - Licensed Short Term Rental, vacation rental in Kailua
Kailua Beachfront - Licensed Short Term Rental, vacation rental in Kailua
Kailua Beachfront - Licensed Short Term Rental, vacation rental in Kailua

Kailua Beachfront - Licensed Short Term Rental

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Available and legal for stays less than 30 days, vacation rental in Kailua
Available and legal for stays less than 30 days, vacation rental in Kailua
Available and legal for stays less than 30 days, vacation rental in Kailua

Available and legal for stays less than 30 days

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Martins Hale - Private 1 Bedroom Studio, vacation rental in Kailua
Martins Hale - Private 1 Bedroom Studio, vacation rental in Kailua
Martins Hale - Private 1 Bedroom Studio, vacation rental in Kailua

Martins Hale - Private 1 Bedroom Studio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage, vacation rental in Kailua
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage, vacation rental in Kailua
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage, vacation rental in Kailua

licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Home in Gated Community Steps from Kailua Beach, vacation rental in Kailua
Luxury Home in Gated Community Steps from Kailua Beach, vacation rental in Kailua
Luxury Home in Gated Community Steps from Kailua Beach, vacation rental in Kailua

Luxury Home in Gated Community Steps from Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Kailua Beach Park Cottage - 2BR, vacation rental in Kailua
Kailua Beach Park Cottage - 2BR, vacation rental in Kailua
Kailua Beach Park Cottage - 2BR, vacation rental in Kailua

Kailua Beach Park Cottage - 2BR

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kaimana Cottage - Walking Distance to beach!, vacation rental in Kailua
Kaimana Cottage - Walking Distance to beach!, vacation rental in Kailua
Kaimana Cottage - Walking Distance to beach!, vacation rental in Kailua

Kaimana Cottage - Walking Distance to beach!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nancy's Kailua Cottage Mauka, vacation rental in Kailua
Nancy's Kailua Cottage Mauka, vacation rental in Kailua
Nancy's Kailua Cottage Mauka, vacation rental in Kailua

Nancy's Kailua Cottage Mauka

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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