Vacation Rentals & Apartments in Kailua

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30 apartments

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Responds fast! avg. 2 hours 7 minutes

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$1,603

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$656

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

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$653

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

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$1,056

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$5,700

Responds fast! avg. 2 hours 7 minutes

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$3,603

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Cozy Beachtown Getaway

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$92

Perfect Beachtown Retreat

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$130

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$350

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$5,400

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$320

“"Lovely"” We stayed at Suite Aloha in September for 11 days. The room was spacious, airy and very comfortable. There was a huge ceiling fan to cool the entire room throughout the day and night. We were awakened by the sweet fragrance of plumeria as it floated through the windows every morning. Lovely! Sabine thought of everything to make our stay comfortable. We were welcomed with fresh fruit and a Beautiful arrangement of fresh Hawaiian flowers. There were beach items available for us to use including a beach umbrella, chairs, mats and beach bag. The location was ideal. We could easily walk to Kailua Beach or to Kailua town. Kailua town has plenty of upscale shops and restaurants. There was even a brand new Target there. We would definitely stay there again. It was lovely!

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$108

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$274

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$186

Lanikai Beachfront - Sunrise over the Mokulua Islands - SPECTACULAR!

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Private outdoor pool (unheated), Towels provided

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$919

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$171

* 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 (unheated), Towels provided

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Price per night from

$172

Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“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 (unheated), Towels provided

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Price per night from

$235

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$224

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Towels provided

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Price per night from

$224

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 (unheated), Towels provided

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Price per night from

$753

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 (unheated), Towels provided

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Price per night from

$1,056

Great rentals within 20 miles that match your search

Laguna Surf

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$344

“Great” We arrived late after 3 weeks in usa mainland, where we did not stop. Getting our keys and into theunit was so easy. It was so close to get to everything from the unit. We had a family of five and with the sofa bed out it was quite tight. Maybe not so many little tables and trinkets. But that would be our only complaint. Everything was just as the photos showed and a great place for a family. We went and did food shopping at safeway, but then found Wallmart cheaper. Thanks heaps for having us

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$194

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$263

Hale Ohana, Pool, Ocean View Home/Hawaii Kai, Oahu 3+BD/3Bath

Hawaii Kai house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$911

NEW Luxury Rental! Kahala Oceanside-6bed/6bath - Sleeps 14

Honolulu house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$4,008

Waikiki Beach Resort

Honolulu house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 1 hour 7 minutes

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$3,434

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: Private outdoor pool (unheated) Towels provided

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Price per night from

$1,586

Match: Private outdoor pool (unheated) Towels provided

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Price per night from

$592

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