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Holiday Rentals in Kailua

Destination
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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
275 rentals in Kailua.
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, holiday rental in Kailua
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, holiday rental in Kailua
Beautiful Kailua Hale Studio Unit.  Walking distance to beach and town, holiday rental in Kailua

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared), holiday rental in Kailua
***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared), holiday rental in Kailua
***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared), holiday rental in Kailua

***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared)

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, holiday rental in Kailua
Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, holiday rental in Kailua
Viewhouse in Lanikai  OCEAN MOKULUA ISLANDS ,  BEACH, LANIKAI NUC 90/BB -0108, holiday rental in Kailua

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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 2
Match: Sleeps
More info
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Sheffield Studio  Walk to Kailua Beach or Town, holiday rental in Kailua
Sheffield Studio  Walk to Kailua Beach or Town, holiday rental in Kailua
Sheffield Studio  Walk to Kailua Beach or Town, holiday rental in Kailua

Sheffield Studio Walk to Kailua Beach or Town

Private Room
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, holiday rental in Kailua
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, holiday rental in Kailua
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach, holiday rental in Kailua

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, holiday rental in Kailua
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, holiday rental in Kailua
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more, holiday 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
More info
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Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., holiday rental in Kailua
Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., holiday rental in Kailua
Beautiful Kailua Hale 1 Bedroom Unit.  Walking distance to beach and town., holiday 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
More info
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Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, holiday rental in Kailua
Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, holiday rental in Kailua
Less than 1 min walk to Kailua Beach- NUC#90/BB -0013, holiday rental in Kailua

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, holiday rental in Kailua
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, holiday rental in Kailua
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LOT, holiday rental in Kailua

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, holiday rental in Kailua
NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, holiday rental in Kailua
NUC 90/BB-0069,  GE-*******-8864-01, TA-*******-8864-01, holiday rental in Kailua

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

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

Unique Relaxing Suite at Lanikai Beach, Legal Vacation Rental

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

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

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

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

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

Ocean View Guest Cottage - 90/TVU-0287

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private & Charming Studio  AC * Strong WiFi  Walk to Beautiful Kailua Beach, holiday rental in Kailua
Private & Charming Studio  AC * Strong WiFi  Walk to Beautiful Kailua Beach, holiday rental in Kailua
Private & Charming Studio  AC * Strong WiFi  Walk to Beautiful Kailua Beach, holiday rental in Kailua

Private & Charming Studio AC * Strong WiFi Walk to Beautiful Kailua Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cottage with Private yard, Walking Distance to Beach & Town, holiday rental in Kailua
Cottage with Private yard, Walking Distance to Beach & Town, holiday rental in Kailua
Cottage with Private yard, Walking Distance to Beach & Town, holiday rental in Kailua

Cottage with Private yard, Walking Distance to Beach & Town

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Available and legal for stays less than 30 days., holiday rental in Kailua
Available and legal for stays less than 30 days., holiday rental in Kailua
Available and legal for stays less than 30 days., holiday rental in Kailua

Available and legal for stays less than 30 days.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, holiday rental in Kailua
Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, holiday rental in Kailua
Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night, holiday 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
More info
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Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, holiday rental in Kailua
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, holiday rental in Kailua
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast, holiday rental in Kailua

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Romantic Oceanview Guesthouse.  Steps from the Beach!, holiday rental in Kailua
Romantic Oceanview Guesthouse.  Steps from the Beach!, holiday rental in Kailua
Romantic Oceanview Guesthouse.  Steps from the Beach!, holiday rental in Kailua

Romantic Oceanview Guesthouse. Steps from the Beach!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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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Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, holiday rental in Kailua
Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, holiday rental in Kailua
Beachside Kailua AC 3min walk to beach! ASK OWNER for available 2023 dates!, holiday rental in Kailua

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Kailua Blue Ocean Breeze Beach Studio, holiday rental in Kailua
Kailua Blue Ocean Breeze Beach Studio, holiday rental in Kailua
Kailua Blue Ocean Breeze Beach Studio, holiday rental in Kailua

Kailua Blue Ocean Breeze Beach Studio

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

Kailua Beachfront - Licensed Rental AUG 26 - SEP 12 AVAILABILITY

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Kailua Beach "The Pink House"  100 Yards from Ocean, holiday rental in Kailua
Kailua Beach "The Pink House"  100 Yards from Ocean, holiday rental in Kailua
Kailua Beach "The Pink House"  100 Yards from Ocean, holiday rental in Kailua

Kailua Beach "The Pink House" 100 Yards from Ocean

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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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Suite By the Sea - a bright and sparkling Apartment, holiday rental in Kailua
Suite By the Sea - a bright and sparkling Apartment, holiday rental in Kailua
Suite By the Sea - a bright and sparkling Apartment, holiday rental in Kailua

Suite By the Sea - a bright and sparkling Apartment

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Heavenly Hale Best Licensed Vacation rental - walk to beach!, holiday rental in Kailua
Heavenly Hale Best Licensed Vacation rental - walk to beach!, holiday rental in Kailua
Heavenly Hale Best Licensed Vacation rental - walk to beach!, holiday rental in Kailua

Heavenly Hale Best Licensed Vacation rental - walk to beach!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Luxury Home in Gated Community Steps from Kailua Beach, holiday rental in Kailua
Luxury Home in Gated Community Steps from Kailua Beach, holiday rental in Kailua
Luxury Home in Gated Community Steps from Kailua Beach, holiday rental in Kailua

Luxury Home in Gated Community Steps from Kailua Beach

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, holiday rental in Kailua
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, holiday rental in Kailua
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow, holiday rental in Kailua

Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Best Price and Location on Beautiful Kailua Beach!, holiday rental in Kailua
Best Price and Location on Beautiful Kailua Beach!, holiday rental in Kailua
Best Price and Location on Beautiful Kailua Beach!, holiday rental in Kailua

Best Price and Location on Beautiful Kailua Beach!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, holiday rental in Kailua
Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, holiday rental in Kailua
Beautiful and Charming Cottage in Lanikai for 2, Close to Beach, a/c, holiday 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
More info
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'Tropical Garden Paradise' Steps to Beach & Very Affordable, holiday rental in Kailua
'Tropical Garden Paradise' Steps to Beach & Very Affordable, holiday rental in Kailua
'Tropical Garden Paradise' Steps to Beach & Very Affordable, holiday rental in Kailua

'Tropical Garden Paradise' Steps to Beach & Very Affordable

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Unique Apartment in excellent location * close to Kailua beach & town, holiday rental in Kailua
Unique Apartment in excellent location * close to Kailua beach & town, holiday rental in Kailua
Unique Apartment in excellent location * close to Kailua beach & town, holiday rental in Kailua

Unique Apartment in excellent location * close to Kailua beach & town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, holiday rental in Kailua
Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, holiday rental in Kailua
Beachfront Plantation Cottage - 3sqm / 2sqm House - Kailua Beach, holiday rental in Kailua

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Gorgeous House, Heated Pool, AC, Steps to Kailua Beach, holiday rental in Kailua
Gorgeous House, Heated Pool, AC, Steps to Kailua Beach, holiday rental in Kailua
Gorgeous House, Heated Pool, AC, Steps to Kailua Beach, holiday rental in Kailua

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

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/solar, holiday rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/solar, holiday rental in Kailua
10min stroll to Kailua Beach -Split Aircon/wireless/kitchen/solar, holiday rental in Kailua

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Absolutely Oceanfront - 60' Waterfall Lap Pool, holiday rental in Kailua
Absolutely Oceanfront - 60' Waterfall Lap Pool, holiday rental in Kailua
Absolutely Oceanfront - 60' Waterfall Lap Pool, holiday rental in Kailua

Absolutely Oceanfront - 60' Waterfall Lap Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Banyan Beach Bungalow, holiday rental in Kailua
The Banyan Beach Bungalow, holiday rental in Kailua
The Banyan Beach Bungalow, holiday rental in Kailua

The Banyan Beach Bungalow

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12, holiday rental in Kailua
Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12, holiday rental in Kailua
Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12, holiday rental in Kailua

Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Licensed Lanikai Beach Rental 100 yards to Lanikai Beach w/AC!, holiday rental in Kailua
Licensed Lanikai Beach Rental 100 yards to Lanikai Beach w/AC!, holiday rental in Kailua
Licensed Lanikai Beach Rental 100 yards to Lanikai Beach w/AC!, holiday rental in Kailua

Licensed Lanikai Beach Rental 100 yards to Lanikai Beach w/AC!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sheffield Suite Walk to Kailua Beach or Town, holiday rental in Kailua
Sheffield Suite Walk to Kailua Beach or Town, holiday rental in Kailua
Sheffield Suite Walk to Kailua Beach or Town, holiday rental in Kailua

Sheffield Suite Walk to Kailua Beach or Town

Private Room
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Footsteps to Hawaii's Best Beach, holiday rental in Kailua
Footsteps to Hawaii's Best Beach, holiday rental in Kailua
Footsteps to Hawaii's Best Beach, holiday rental in Kailua

Footsteps to Hawaii's Best Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern 1 Bedroom AC Walk to Kailua Beach, holiday rental in Kailua
Modern 1 Bedroom AC Walk to Kailua Beach, holiday rental in Kailua
Modern 1 Bedroom AC Walk to Kailua Beach, holiday rental in Kailua

Modern 1 Bedroom AC Walk to Kailua Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Last Minute Deal! Stylish 1BR Apartment with AC, Steps from Kailua Beach, holiday rental in Kailua
Last Minute Deal! Stylish 1BR Apartment with AC, Steps from Kailua Beach, holiday rental in Kailua
Last Minute Deal! Stylish 1BR Apartment with AC, Steps from Kailua Beach, holiday rental in Kailua

Last Minute Deal! Stylish 1BR Apartment with AC, Steps from Kailua Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Kailua Beachfront - SHORT TERM LICENSED RENTAL, holiday rental in Kailua
Kailua Beachfront - SHORT TERM LICENSED RENTAL, holiday rental in Kailua
Kailua Beachfront - SHORT TERM LICENSED RENTAL, holiday rental in Kailua

Kailua Beachfront - SHORT TERM LICENSED RENTAL

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Entire Guest Cottage for your Enchanted Getaway, holiday rental in Kailua
Entire Guest Cottage for your Enchanted Getaway, holiday rental in Kailua
Entire Guest Cottage for your Enchanted Getaway, holiday rental in Kailua

Entire Guest Cottage for your Enchanted Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-50 of 275
Frequently Asked Questions about Kailua