Vacation Rentals & Apartments in Kailua

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“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!

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Price per night from

$235

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$171

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$186

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Kailua Home w/Spectacular Views, Newly Renovated

Kailua house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Bicycles available, Microwave

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Price per night from

$653

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$5,430

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$350

* Private & Charming Studio * AC * strong WIFi *

Kailua studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$93

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

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Bicycles available, Microwave

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Price per night from

$149

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$142

*Beautiful and Cheerful Hale Mokolea in Lanikai*

Kailua cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$245

Island Style Homebase * 2 bedroom * 1 bath * AC* full kitchen *Washer/Dryer

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$197

Spacious 3-Bedroom, 2-Bath Apartment with Kitchen and AC

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$242

*A place of peace, where heaven meets the ocean*

Kailua house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$594

*Affordable Island Getaway with private yard *

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$161

Suite By the Sea - a bright and sparkling Apartment

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$137

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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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!

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Price per night from

$108

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

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Price per night from

$274

* Marbella Lane - Sunshine Seascape | Ocean View

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 10 minutes

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$172

Lanikai Beachfront - Sunrise over the Mokulua Islands - SPECTACULAR!

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$919

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$5,700

Private Beachlane House with 2 bedrooms * AC

Kailua house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$359

Stylish 1-Bedroom Apartment with AC* Just Moments from Kailua Beach

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$149

* SPRING SPECIAL * Delightful & Spacious * 2 bedroom * 2 bath Apartment *AC

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$233

Steps to the beach * upstairs Apartment with 3 bedrooms & 2 bath* AC

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$284

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

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Price per night from

$224

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$224

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

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Price per night from

$1,056

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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Price per night from

$1,596

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: Bicycles available, Microwave

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Price per night from

$753

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Bicycles available, Microwave

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Price per night from

$1,603

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Bicycles available, Microwave

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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

1 of 2 match: Bicycles available, Microwave

1 of 2 filters match

Price per night from

$653

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Bicycles available, Microwave

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Price per night from

$3,603

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Price per night from

$2,382

Great rentals within 20 miles that match your search

Hawaiian King- Modern Elegance with Hawaiian Charm

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$166

Ala Moana Hotel rivaled Condo

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Great central location” Cozy condo, well provisioned with cooking supplies, linens and towels. The owner was very responsive to questions and called during my stay to be sure all was well. The room is small and I'm not sure how 4 people would fit as there was a queen size bed and a chair that converted to a single bed. The sliding glass doors make the room feel larger but there is no balcony. As it is located next to the Ala Moana center, food, shopping and transportation are readily available. The bus system is very easy to use.

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Price per night from

$193

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Price per night from

$457

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rentals in Kailua

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