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Kailua Vacation Rentals

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Bathrooms

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5 mi
204 rentals in Kailua.
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, vacation rental in Kailua
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, vacation rental in Kailua
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, vacation rental in Kailua

Beautiful Kailua Hale Studio Unit. Walking distance to beach and town

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Beachfront Rental, vacation rental in Kailua
Private Beachfront Rental, vacation rental in Kailua
Private Beachfront Rental, vacation rental in Kailua

Private Beachfront Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, vacation rental in Kailua
Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, vacation rental in Kailua
Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, vacation rental in Kailua

Viewhouse in Lanikai OCEAN MOKULUA ISLANDS , BEACH, LANIKAI NUC 90/BB -0108

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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PRIVATE BEACHFRONT RENTAL, vacation rental in Kailua
PRIVATE BEACHFRONT RENTAL, vacation rental in Kailua
PRIVATE BEACHFRONT RENTAL, vacation rental in Kailua

PRIVATE BEACHFRONT RENTAL

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, vacation rental in Kailua
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, vacation rental in Kailua
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, vacation rental in Kailua

Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, vacation rental in Kailua
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, vacation rental in Kailua
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, vacation rental in Kailua

Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., vacation rental in Kailua
Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., vacation rental in Kailua
Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., vacation rental in Kailua

Beautiful Kailua Hale 1 Bedroom Unit. Walking distance to beach and town.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, vacation rental in Kailua
Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, vacation rental in Kailua
Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, vacation rental in Kailua

Less than 1 min walk to Kailua Beach- NUC#90/BB -0013

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, vacation rental in Kailua
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, vacation rental in Kailua
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, vacation rental in Kailua

BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, vacation rental in Kailua
NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, vacation rental in Kailua
NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, vacation rental in Kailua

NUC 90/BB-0069, GE-*******-8864-01, TA-*******-8864-01

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Unique Relaxing Suite at Lanikai Beach, Legal Vacation Rental, vacation rental in Kailua
Unique Relaxing Suite at Lanikai Beach, Legal Vacation Rental, vacation rental in Kailua
Unique Relaxing Suite at Lanikai Beach, Legal Vacation Rental, vacation rental in Kailua

Unique Relaxing Suite at Lanikai Beach, Legal Vacation Rental

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa, vacation rental in Kailua
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa, vacation rental in Kailua
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa, vacation rental in Kailua

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031, vacation rental in Kailua
Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031, vacation rental in Kailua
Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031, vacation rental in Kailua

Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ocean View Guest Cottage - 90/TVU-0287, vacation rental in Kailua
Ocean View Guest Cottage - 90/TVU-0287, vacation rental in Kailua
Ocean View Guest Cottage - 90/TVU-0287, vacation rental in Kailua

Ocean View Guest Cottage - 90/TVU-0287

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage with Private yard, Walking Distance to Beach & Town, vacation rental in Kailua
Cottage with Private yard, Walking Distance to Beach & Town, vacation rental in Kailua
Cottage with Private yard, Walking Distance to Beach & Town, vacation rental in Kailua

Cottage with Private yard, Walking Distance to Beach & Town

Rental Home
1 bedroom
1 bathroom
Sleeps 4
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.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, vacation rental in Kailua
Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, vacation rental in Kailua
Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, vacation rental in Kailua

Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, vacation rental in Kailua
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, vacation rental in Kailua
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, vacation rental in Kailua

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

Rental Home
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Romantic Oceanview Guesthouse.  Steps from the Beach!, vacation rental in Kailua
Romantic Oceanview Guesthouse.  Steps from the Beach!, vacation rental in Kailua
Romantic Oceanview Guesthouse.  Steps from the Beach!, vacation rental in Kailua

Romantic Oceanview Guesthouse. Steps from the Beach!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, vacation rental in Kailua
Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, vacation rental in Kailua
Awesome Beachside Cottage Located Just Steps Away from Kailua Beach, vacation rental in Kailua

Awesome Beachside Cottage Located Just Steps Away from Kailua Beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, vacation rental in Kailua
Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, vacation rental in Kailua
Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, vacation rental in Kailua

Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Kailua Blue Ocean Breeze Beach Studio, vacation rental in Kailua
Kailua Blue Ocean Breeze Beach Studio, vacation rental in Kailua
Kailua Blue Ocean Breeze Beach Studio, vacation rental in Kailua

Kailua Blue Ocean Breeze Beach Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kailua Beachfront - Licensed Rental AUG 26 - SEP 12 AVAILABILITY, vacation rental in Kailua
Kailua Beachfront - Licensed Rental AUG 26 - SEP 12 AVAILABILITY, vacation rental in Kailua
Kailua Beachfront - Licensed Rental AUG 26 - SEP 12 AVAILABILITY, vacation rental in Kailua

Kailua Beachfront - Licensed Rental AUG 26 - SEP 12 AVAILABILITY

Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Kailua Beach "The Pink House"  100 Yards from Ocean, vacation rental in Kailua
Kailua Beach "The Pink House"  100 Yards from Ocean, vacation rental in Kailua
Kailua Beach "The Pink House"  100 Yards from Ocean, vacation rental in Kailua

Kailua Beach "The Pink House" 100 Yards from Ocean

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Heavenly Hale Best Licensed Vacation rental - walk to beach!, vacation rental in Kailua
Heavenly Hale Best Licensed Vacation rental - walk to beach!, vacation rental in Kailua
Heavenly Hale Best Licensed Vacation rental - walk to beach!, vacation rental in Kailua

Heavenly Hale Best Licensed Vacation rental - walk to beach!

Condo/Apartment
2 bedrooms
2 bathrooms
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, vacation rental in Kailua
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, vacation rental in Kailua
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, vacation rental in Kailua

Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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!

Rental Home
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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-30 of 204
Frequently Asked Questions about Kailua






Kailua Vacation Rentals
Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.
A Kailua Vacation
Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.
Family-Friendly Kailua
From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.
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