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Kailua Rentals with Pools

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53 rentals in Kailua.
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Licensed Short Term Rental Beach Front - Kailua
Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps, All pools
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The Perfect Kailua Retreat!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Beachside Kailua AC 3min walk to beach! INQUIRE for Fall & Winter 2022 dates!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Great Location, Large Pool, Koi Pond, Walk to Kailua Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Secluded Home w/ Pool in Gated Community, Steps From Beautiful Kailua Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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5 Minute Walk to Kailua Beach
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Kahela - Paradise for Rent
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Luxury Home in Gated Community Steps from Kailua Beach
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Gorgeous House, Heated Pool, AC, Steps to Kailua Beach
Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed-$199 Per Night
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Steps to Lanikai Beach~3 living spaces w/pool
Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views
Rental Home
2 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, All pools
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Hale Maluhia Lanikai - Special On Beautiful Lanikai Home!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Large, beautiful, updated home w/pool, AC, mins from beach in Kailua!
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Mokulua Aina~Lanikai Steps to Lanikai Beach. SPECIAL FALL RATES!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Steps to Kailua Beach; Newly Remodeled, Spacious home w/heated pool.
Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Fabulous Luxury Kailua Beachfront Private pool and Hot Tub
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Hawaiian Dream Beachfront Oceanfront paradise
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Steps to Lanikai Beach~3 living spaces w/pool
Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Orchid House | New Low Promo Rates for Fall 2023!!
Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps, All pools
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Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Mokulua Aina~Lanikai Steps to Lanikai Beach. SPECIAL FALL RATES!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Steps to Kailua Beach; Newly Remodeled, Spacious home w/heated pool.
Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Beach Front Kailua with pool. October CANCELLATION - REDUCED RATE!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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CHRISTMAS CANCELLATION - BEACH FRONT KAILUA W/POOL. CALL NOW!
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Aloha Tropical Hideaway
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
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Tropical Pool Cottage close to Kailua Beach
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Last minute opening! Lovely Pool Studio with private entrance & bath
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach: Lanikai Breeze
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Beautiful Lanikai Oceanfront Villa With Fabulous Views-private Pool and Hot Tub
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Luxurious Kailua Home w/Pool Oasis & A/C, Near Beaches and Shopping - Maluhia
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, All pools
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Pristine Kailua Beach just a few steps away ( $13k Monthly Special)
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Get Your Toes in the Sand .... Kailua Beachfront!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Enjoy watching for Sea Turtles off your Ocean Front Deck!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Luxury Beachfront Kai Moena Estate w/Pool, Spa, AC, Sauna, Tennis Court & More!
Rental Home
9 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Pristine Kailua Retreat w/AC, Lush Pool, & Spa Oasis, Walk to Beach: Hale Ohana
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Lavish Oceanview Estate w/Pool, Spa, AC & Mokulua Isle Views: Lanikai Hillside
Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Hawaiian Dream - Beachfront /Oceanfront paradise. by RedAwning
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Secluded Mountainside Home w/ Private Pool & Ocean Views: Hale Lani
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Beach Front Kailua with pool. AUGUST CANCELLATION - CALL FOR RATES!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Beautiful Ohana Studio
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Island Jewel
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Amazing � Kailua Beach House � Pool! Game Room! 1 House from Beach
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Island breeze Hale ($10,800 monthly stay)
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, All pools
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3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
Rental Home
7 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps, All pools
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LANIKAI SUITE - Spacious 1-BR 1-BA; located 3 houses from famous LANIKAI Beach
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Lanikai Lux Living
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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LANIKAI Plantation Cottage located only 3 houses from famous Lanikai Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Modern Beachfront Estate w/Private Pool/Spa, Ocean View & AC: Kailua Beach Villa
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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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.