Vacation Rentals & Apartments in Kailua

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Responds fast! avg. 2 hours 7 minutes

Match: Iron Private outdoor pool (heated)

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Price per night from

$985

Steps to Kailua Beach; Newly Remodeled, Spacious home w/heated pool.

Kailua house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 7 minutes

Match: Iron Private outdoor pool (heated)

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Price per night from

$1,596

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Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Iron, Private outdoor pool (heated)

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Price per night from

$3,603

Kailua Home w/Spectacular Views, Newly Renovated

Kailua house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$651

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$319

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$273

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$185

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$171

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$5,700

* Marbella Lane - Sunshine Seascape | Ocean View

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 10 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$172

“You will be very happy you stayed here” We are very experienced travelers and also rent our vacation home so have a perspective on both sides of this equation. We are a family of four with two teenage daughters (ages 14 and 13 at time of the stay). If you rent from Patty you will be very happy you made the decision. 1) Hosts - Patty was so welcoming, friendly and helpful without ever being intrusive. She was a wealth of knowledge and was so willing to share her insights to ensure we hit the best spots at the right times to ensure a great experience. 2) Apartment - The pictures are very accurate so you really get what you see. The apartment has very "homey" feeling. The decor is local and tasteful, the kitchen fully equipped. The Lanai had really nice breezes and sunrises. It also had hooks which came in handy when drying things. While we didn't watch much TV there were plenty of options (cable, netflix, pandora) as well as a small stereo system. There were games to play, books to read (including several on Hawaii that we loved), and the all-important washer/dryer. 3) The Stuff - One of the things we loved about the apartment was the plethora recreational toys at our disposal. Beach chairs, umbrellas, boogie boards, snorkels, masks, coolers, sup's, Kayaks, bikes, etc. If you needed it, they had it which was huge for a family that spent everyday on the ridiculously nice beaches a short drive away. 4) The Location - Check it out on the map. It sits just above town in a neighborhood. It is not walking distance from the beach or town but a 5 minute drive (and free street parking) gets you there before you know it. It is walking distance to a great yoga co-op (Aloha Yoga Kula) which we went to several times and loved. Some may want to be closer to the action but we found the location close enough. All in all, this is a fantastic rental and we thought a great value. The personal touch offered by Patty puts it over the top. Do yourself a favor and book it before someone else does!

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$234

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$223

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$223

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$656

Kailua Beachfront~private~newly renovated home w/stunning views & spa

Kailua house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$1,056

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!

Kailua house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$653

Makani Moana - Lanikai; w/spectacular views of the Mokulua Islands; AC

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (heated), Iron

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Price per night from

$753

Great rentals within 20 miles that match your search

Match: Iron Private outdoor pool (heated)

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Price per night from

$456

Luxury Home w/heated pool/spa steps from Kahala Beach

Honolulu house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Match: Iron Private outdoor pool (heated)

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Price per night from

$1,586

“Great location at an affordable price!” This little condo was perfect for our needs. The location served as the perfect place for me to experience Waikiki for the first time. Just a short walk to Waikiki beach, Dukes, Island Vintage coffee, and shopping. We really only used the room for showers and sleeping (3 days 2 nights) so the size was just fine. If the stay was longer I would have preferred a more conventional kitchen with a range but we ended up eating out for the most part. Mark was great, very accessible by phone and took care of a little hiccup with the cleaner timely and professionally. I would absolutely stay here again for short trips to Waikiki!

Match: Iron Private outdoor pool (heated)

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Price per night from

$126

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