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Kailua Vacation Rentals

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5 mi
199 rentals in Kailua.
Viewhouse in Lanikai  BEST LOCATION ,  LANIKAI NUC 90/BB -0108, vacation rental in Kailua
Viewhouse in Lanikai  BEST LOCATION ,  LANIKAI NUC 90/BB -0108, vacation rental in Kailua
Viewhouse in Lanikai  BEST LOCATION ,  LANIKAI NUC 90/BB -0108, vacation rental in Kailua

Viewhouse in Lanikai BEST LOCATION , 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 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
1 bedroom
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
5 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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Lovely Private Kailua Cottage, vacation rental in Kailua
Lovely Private Kailua Cottage, vacation rental in Kailua
Lovely Private Kailua Cottage, vacation rental in Kailua

Lovely Private Kailua Cottage

Rental Home
2 bedrooms
2 bathrooms
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
1 bedroom
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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Amazing & Large Kailua Beachfront for up to 14 guests, vacation rental in Kailua
Amazing & Large Kailua Beachfront for up to 14 guests, vacation rental in Kailua
Amazing & Large Kailua Beachfront for up to 14 guests, vacation rental in Kailua

Amazing & Large Kailua Beachfront for up to 14 guests

Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
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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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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Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, vacation rental in Kailua
Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, vacation rental in Kailua
Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, vacation rental in Kailua

Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Huge House, Heated Pool, AC, Steps to Kailua Beach, vacation rental in Kailua
Huge House, Heated Pool, AC, Steps to Kailua Beach, vacation rental in Kailua
Huge House, Heated Pool, AC, Steps to Kailua Beach, vacation rental in Kailua

Huge House, Heated Pool, AC, Steps to Kailua Beach

Rental Home
8 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Absolutely Oceanfront - 60' Waterfall Lap Pool, vacation rental in Kailua
Absolutely Oceanfront - 60' Waterfall Lap Pool, vacation rental in Kailua
Absolutely Oceanfront - 60' Waterfall Lap Pool, vacation rental in Kailua

Absolutely Oceanfront - 60' Waterfall Lap Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Location on Kailua Beach - Licensed Short Term Rental, vacation rental in Kailua
Perfect Location on Kailua Beach - Licensed Short Term Rental, vacation rental in Kailua
Perfect Location on Kailua Beach - Licensed Short Term Rental, vacation rental in Kailua

Perfect Location on Kailua Beach - Licensed Short Term Rental

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Kailua  Beach  Studio, vacation rental in Kailua
Kailua  Beach  Studio, vacation rental in Kailua
Kailua  Beach  Studio, vacation rental in Kailua

Kailua Beach Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Suite By the Sea - a bright and sparkling Apartment, vacation rental in Kailua
Suite By the Sea - a bright and sparkling Apartment, vacation rental in Kailua
Suite By the Sea - a bright and sparkling Apartment, vacation rental in Kailua

Suite By the Sea - a bright and sparkling Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Studio with King Bed & Private Bath - AC and Steps from the Beach!, vacation rental in Kailua
Charming Studio with King Bed & Private Bath - AC and Steps from the Beach!, vacation rental in Kailua
Charming Studio with King Bed & Private Bath - AC and Steps from the Beach!, vacation rental in Kailua

Charming Studio with King Bed & Private Bath - AC and Steps from the Beach!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kailua Beach Cottage with A/C, vacation rental in Kailua
Kailua Beach Cottage with A/C, vacation rental in Kailua
Kailua Beach Cottage with A/C, vacation rental in Kailua

Kailua Beach Cottage with A/C

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Beach Cottage, vacation rental in Kailua
Charming Beach Cottage, vacation rental in Kailua
Charming Beach Cottage, vacation rental in Kailua

Charming Beach Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Steps to the Beach Guesthouse, vacation rental in Kailua
Steps to the Beach Guesthouse, vacation rental in Kailua
Steps to the Beach Guesthouse, vacation rental in Kailua

Steps to the Beach Guesthouse

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Beachside Bungalow, vacation rental in Kailua
Beautiful Beachside Bungalow, vacation rental in Kailua
Beautiful Beachside Bungalow, vacation rental in Kailua

Beautiful Beachside Bungalow

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale, vacation rental in Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale, vacation rental in Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale, vacation rental in Kailua

Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy 1 bedroom steps to white sand beach, vacation rental in Kailua
Comfy 1 bedroom steps to white sand beach, vacation rental in Kailua
Comfy 1 bedroom steps to white sand beach, vacation rental in Kailua

Comfy 1 bedroom steps to white sand beach

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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� Charming Apartment in Prime Location – Steps from Kailua Beach & Town �, vacation rental in Kailua
� Charming Apartment in Prime Location – Steps from Kailua Beach & Town �, vacation rental in Kailua
� Charming Apartment in Prime Location – Steps from Kailua Beach & Town �, vacation rental in Kailua

� Charming Apartment in Prime Location – Steps from Kailua Beach & Town �

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Charming Kailua Studio: Your Tranquil Oasis Awaits, vacation rental in Kailua
Charming Kailua Studio: Your Tranquil Oasis Awaits, vacation rental in Kailua
Charming Kailua Studio: Your Tranquil Oasis Awaits, vacation rental in Kailua

Charming Kailua Studio: Your Tranquil Oasis Awaits

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Light and breezy Kailua apartment, vacation rental in Kailua
Light and breezy Kailua apartment, vacation rental in Kailua
Light and breezy Kailua apartment, vacation rental in Kailua

Light and breezy Kailua apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, vacation rental in Kailua
'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, vacation rental in Kailua
'Kailua Lani Luxury Suite' short walk to Kailua and Lanikai Beaches, vacation rental in Kailua

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tradewind Bungalow, in Kailua on Oahu, vacation rental in Kailua
Tradewind Bungalow, in Kailua on Oahu, vacation rental in Kailua
Tradewind Bungalow, in Kailua on Oahu, vacation rental in Kailua

Tradewind Bungalow, in Kailua on Oahu

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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____Cute 2 Bedrooms Plantation Home with AC_____, vacation rental in Kailua
____Cute 2 Bedrooms Plantation Home with AC_____, vacation rental in Kailua
____Cute 2 Bedrooms Plantation Home with AC_____, vacation rental in Kailua

____Cute 2 Bedrooms Plantation Home with AC_____

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Penthouse View in Lanikai  LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3., vacation rental in Kailua
Penthouse View in Lanikai  LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3., vacation rental in Kailua
Penthouse View in Lanikai  LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3., vacation rental in Kailua

Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sept. 2023 Reduced Rate - Steps away from Kailua Beach Park!, vacation rental in Kailua
Sept. 2023 Reduced Rate - Steps away from Kailua Beach Park!, vacation rental in Kailua
Sept. 2023 Reduced Rate - Steps away from Kailua Beach Park!, vacation rental in Kailua

Sept. 2023 Reduced Rate - Steps away from Kailua Beach Park!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach, vacation rental in Kailua
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach, vacation rental in Kailua
Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach, vacation rental in Kailua

Stylish 1BR Apartment with AC, Full Kitchen & W/D - Just Steps to the Beach

Condo/Apartment
2 bedrooms
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

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy 2 Bedroom Cottage - Steps from the Beach, vacation rental in Kailua
Cozy 2 Bedroom Cottage - Steps from the Beach, vacation rental in Kailua
Cozy 2 Bedroom Cottage - Steps from the Beach, vacation rental in Kailua

Cozy 2 Bedroom Cottage - Steps from the Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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�Last-Minute Deal! 2BR Apt w/ Stunning Mountain Views, Full Kitchen, A/C �, vacation rental in Kailua
�Last-Minute Deal! 2BR Apt w/ Stunning Mountain Views, Full Kitchen, A/C �, vacation rental in Kailua
�Last-Minute Deal! 2BR Apt w/ Stunning Mountain Views, Full Kitchen, A/C �, vacation rental in Kailua

�Last-Minute Deal! 2BR Apt w/ Stunning Mountain Views, Full Kitchen, A/C �

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House, vacation rental in Kailua
Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House, vacation rental in Kailua
Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House, vacation rental in Kailua

Private Luxury Home, Steps from the Beach w/ AC, Ranch Beach House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Serene Lanikai House Near the Beach w/Outdoor BBQ & Close to Shopping Center, vacation rental in Kailua
Serene Lanikai House Near the Beach w/Outdoor BBQ & Close to Shopping Center, vacation rental in Kailua
Serene Lanikai House Near the Beach w/Outdoor BBQ & Close to Shopping Center, vacation rental in Kailua

Serene Lanikai House Near the Beach w/Outdoor BBQ & Close to Shopping Center

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Beachlane House with 2 bedrooms * AC, vacation rental in Kailua
Private Beachlane House with 2 bedrooms * AC, vacation rental in Kailua
Private Beachlane House with 2 bedrooms * AC, vacation rental in Kailua

Private Beachlane House with 2 bedrooms * AC

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen, vacation rental in Kailua
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen, vacation rental in Kailua
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen, vacation rental in Kailua

Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family cottage available July 17-August 1., vacation rental in Kailua
Family cottage available July 17-August 1., vacation rental in Kailua
Family cottage available July 17-August 1., vacation rental in Kailua

Family cottage available July 17-August 1.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Pilipu Palms 2, vacation rental in Kailua
Pilipu Palms 2, vacation rental in Kailua
Pilipu Palms 2, vacation rental in Kailua

Pilipu Palms 2

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Steps to quiet part of Kailua beach, renovated, entire home, A/C, perfection, vacation rental in Kailua
Steps to quiet part of Kailua beach, renovated, entire home, A/C, perfection, vacation rental in Kailua
Steps to quiet part of Kailua beach, renovated, entire home, A/C, perfection, vacation rental in Kailua

Steps to quiet part of Kailua beach, renovated, entire home, A/C, perfection

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Kailua Condo / Townhouse on Oahu 30 consecutive day rental period, vacation rental in Kailua
Kailua Condo / Townhouse on Oahu 30 consecutive day rental period, vacation rental in Kailua
Kailua Condo / Townhouse on Oahu 30 consecutive day rental period, vacation rental in Kailua

Kailua Condo / Townhouse on Oahu 30 consecutive day rental period

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tropical Masterpiece in the Heart of Lanikai, vacation rental in Kailua
Tropical Masterpiece in the Heart of Lanikai, vacation rental in Kailua
Tropical Masterpiece in the Heart of Lanikai, vacation rental in Kailua

Tropical Masterpiece in the Heart of Lanikai

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach, vacation rental in Kailua
Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach, vacation rental in Kailua
Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach, vacation rental in Kailua

Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 199
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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