Vacation Rentals & Apartments in Kailua

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Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$224

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

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$274

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

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Price per night from

$224

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$320

Responds fast! avg. 2 hours 7 minutes

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$1,606

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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$1,058

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$657

“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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$235

“"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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$108

Private Beachlane House with 2 bedrooms * AC

Kailua house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$359

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

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$233

* Private & Charming Studio * AC * strong WIFi *

Kailua studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$93

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

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$149

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

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$198

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

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$754

Lanikai Beachfront - Sunrise over the Mokulua Islands - SPECTACULAR!

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$921

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

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$242

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$143

*Affordable Island Getaway with private yard *

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$161

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$186

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

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$285

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

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Price per night from

$654

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$351

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$171

Suite By the Sea - a bright and sparkling Apartment

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$137

Responds fast! avg. 2 hours 7 minutes

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$5,438

Kailua Home w/Spectacular Views, Newly Renovated

Kailua house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$654

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

Responds fast! avg. 2 hours 7 minutes

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$5,708

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

Kailua house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$594

*Beautiful and Cheerful Hale Mokolea in Lanikai*

Kailua cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$246

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$2,385

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

$1,599

* Marbella Lane - Sunshine Seascape | Ocean View

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 10 minutes

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Price per night from

$172

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$3,608

Great rentals within 20 miles that match your search

16TH FLOOR CONDO -1.5 BLOCK FROM WAIKIKI BEACH

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$213

Come to paradise! Enjoy the calmness & birds singing in the morning!

Honolulu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$218

Hawaiian King- Modern Elegance with Hawaiian Charm

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$167

Viewing 38 of 152
rentals in Kailua

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