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Kailua Rentals with Pools

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107 rentals in Kailua.
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SUITE ALOHA – Remodeled, Romantic Island Retreat, vacation rental in Kailua

SUITE ALOHA – Remodeled, Romantic Island Retreat

1 bedroom
1 bathroom
Sleeps 2
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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Perfect Kailua Retreat!, vacation rental in Kailua

The Perfect Kailua Retreat!

0 bedrooms
1 bathroom
Sleeps 2
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

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Place in Paradise~Kailua Beach Front ~ Legal Short Term Rental 90/TVU-0248, vacation rental in Kailua

Place in Paradise~Kailua Beach Front ~ Legal Short Term Rental 90/TVU-0248

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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KAILUA-STEPS TO THE BEACH, vacation rental in Kailua

KAILUA-STEPS TO THE BEACH

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates, vacation rental in Kailua

Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Blue Ginger Cottage/Mele Hale, vacation rental in Kailua

Blue Ginger Cottage/Mele Hale

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Close to the Beautiful Kailua Beach-A/C-Full Kitchen-WiFi-Covered Patio-Laundry, vacation rental in Kailua

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Barefoot living on Lanikai Beach -- BEACHFRONT!, vacation rental in Kailua

Barefoot living on Lanikai Beach -- BEACHFRONT!

1 bedroom
1 bathroom
Sleeps 4
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Best Price and Location on Beautiful Kailua Beach!, vacation rental in Kailua

Best Price and Location on Beautiful Kailua Beach!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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1 house from the beach - solar heated pool - AC - Contact Owner for Rates, vacation rental in Kailua

1 house from the beach - solar heated pool - AC - Contact Owner for Rates

4 bedrooms
3 bathrooms
Sleeps 7
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

3 bedrooms
2 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.

2 bedrooms
1 bathroom
Sleeps 4
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Private Beachside Kailua Home - Remodeled w/AC - 3 min walk to beach!, vacation rental in Kailua

Private Beachside Kailua Home - Remodeled w/AC - 3 min walk to beach!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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5 Minute Walk to Kailua Beach, vacation rental in Kailua

5 Minute Walk to Kailua Beach

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Kailua Beach Vacation Cottage, vacation rental in Kailua

Kailua Beach Vacation Cottage

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Kahela - Paradise for Rent, vacation rental in Kailua

Kahela - Paradise for Rent

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beachside Kailua,  Immaculate & Private 1 BR,  stones throw to Kailua Beach!, vacation rental in Kailua

Beachside Kailua, Immaculate & Private 1 BR, stones throw to Kailua Beach!

1 bedroom
1 bathroom
Sleeps 4
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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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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A Month in Paradise!  - 250 Steps to the Beach, vacation rental in Kailua

A Month in Paradise! - 250 Steps to the Beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful Kailua Home, looking for a family to share it's Aloha, vacation rental in Kailua

Beautiful Kailua Home, looking for a family to share it's Aloha

4 bedrooms
3 bathrooms
Sleeps 10
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

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Amazing � Kailua Beach House � Pool! Game Room! 1 House from Beach, vacation rental in Kailua

Amazing � Kailua Beach House � Pool! Game Room! 1 House from Beach

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Walking Distance to Kailua Town & Kailua Beach, vacation rental in Kailua

Walking Distance to Kailua Town & Kailua Beach

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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CHRISTMAS DATES AVAILABLE!! Prime Location Across from Kailua Beach Park w/AC, vacation rental in Kailua

CHRISTMAS DATES AVAILABLE!! Prime Location Across from Kailua Beach Park w/AC

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Uluhale: House of the Breadfruit Tree: Steps to Lanikai Beach, vacation rental in Kailua

Uluhale: House of the Breadfruit Tree: Steps to Lanikai Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk to Beach,  Bright, Spacious studio. Upstairs w/ mountain view, vacation rental in Kailua

Walk to Beach, Bright, Spacious studio. Upstairs w/ mountain view

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Nancy's Kailua Cottage Mauka, vacation rental in Kailua

Nancy's Kailua Cottage Mauka

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Steps to the Beach Guesthouse, vacation rental in Kailua

Steps to the Beach Guesthouse

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3 Bedroom Kailua Fire Captain's Home, Simple & Clean with Max Speed WiFi, vacation rental in Kailua

3 Bedroom Kailua Fire Captain's Home, Simple & Clean with Max Speed WiFi

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Very Close To Kailua Town And Beach! Last minute discounted rates!, vacation rental in Kailua

Very Close To Kailua Town And Beach! Last minute discounted rates!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kailua Beach Park Cottage - 1BR, vacation rental in Kailua

Kailua Beach Park Cottage - 1BR

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Little Yellow Cottage: Steps to Lanikai Beach, vacation rental in Kailua

Little Yellow Cottage: Steps to Lanikai Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wow!   Home just steps from the Beach with Pool, vacation rental in Kailua

Wow! Home just steps from the Beach with Pool

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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42 feet from Kailua Beach. Exceptional Family Getaway for Lifetime Memories., vacation rental in Kailua

42 feet from Kailua Beach. Exceptional Family Getaway for Lifetime Memories.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Prime Location! Sleeps 8 next to BEST beaches in Kailua & Lani Kai, vacation rental in Kailua

Prime Location! Sleeps 8 next to BEST beaches in Kailua & Lani Kai

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Nancy's Kailua Cottage Makai, vacation rental in Kailua

Nancy's Kailua Cottage Makai

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach, vacation rental in Kailua

New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Tropical Garden Paradise' Steps to Beach & Very Affordable, vacation rental in Kailua

'Tropical Garden Paradise' Steps to Beach & Very Affordable

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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$4500/30-day off-season rate in Lanikai (30-day minimum stay), vacation rental in Kailua

$4500/30-day off-season rate in Lanikai (30-day minimum stay)

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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30 day minimum  ~ Large, comfortable, tropical landscape!!, vacation rental in Kailua

30 day minimum ~ Large, comfortable, tropical landscape!!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A New Beautiful Kailua Home, near the beach and Kailua town, vacation rental in Kailua

A New Beautiful Kailua Home, near the beach and Kailua town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Kailua Beach Park Cottage - 2BR, vacation rental in Kailua

Kailua Beach Park Cottage - 2BR

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beachfront Kailua, Oahu, vacation rental in Kailua

Beachfront Kailua, Oahu

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Beautiful Kailua Home, near the beach and 6 minutes walk to Kailua town, vacation rental in Kailua

New Beautiful Kailua Home, near the beach and 6 minutes walk to Kailua town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Secluded Beach Bungalow with Private Garden, vacation rental in Kailua

Secluded Beach Bungalow with Private Garden

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $199, vacation rental in Kailua

Absolutely Oceanfront - Legal - 60ft waterfall lap pool - $199

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Plantation Charm in Kailua, vacation rental in Kailua

Plantation Charm in Kailua

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Nice 2bd/1bath. 3blk. Walk to beach. Private entry& bathroom, vacation rental in Kailua

Nice 2bd/1bath. 3blk. Walk to beach. Private entry& bathroom

2 bedrooms
1 bathroom
Sleeps 4
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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.
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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.