Vacation Rentals & Apartments in Kailua

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Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Fridge Sea view

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Price per night from

$171

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Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

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Price per night from

$5,430

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

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Price per night from

$350

* Private & Charming Studio * AC * strong WIFi *

Kailua studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Fridge

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Price per night from

$93

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

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Fridge

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Price per night from

$242

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

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Sea view, Fridge

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Price per night from

$149

*Beautiful and Cheerful Hale Mokolea in Lanikai*

Kailua cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Fridge

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Price per night from

$245

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

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Fridge

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Price per night from

$197

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

Kailua house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Sea view, Fridge

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Price per night from

$594

Suite By the Sea - a bright and sparkling Apartment

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Fridge

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Price per night from

$137

*Affordable Island Getaway with private yard *

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Fridge

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Price per night from

$161

1 of 2 match: Sea view, Fridge

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Price per night from

$142

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Sea view, Fridge

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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: Sea view, Fridge

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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: Sea view, Fridge

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Price per night from

$274

1 of 2 match: Sea view, Fridge

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Price per night from

$186

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

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Price per night from

$5,700

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: Sea view, Fridge

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Price per night from

$919

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

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Sea view, Fridge

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Price per night from

$284

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

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Sea view, Fridge

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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

1 of 2 match: Sea view, Fridge

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Price per night from

$233

Private Beachlane House with 2 bedrooms * AC

Kailua house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Sea view, Fridge

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Price per night from

$359

* Marbella Lane - Sunshine Seascape | Ocean View

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 10 minutes

1 of 2 match: Sea view, Fridge

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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: Sea view, Fridge

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Price per night from

$235

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

1 of 2 match: Sea view, Fridge

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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: Sea view, Fridge

1 of 2 filters match

Price per night from

$224

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

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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: Sea view, Fridge

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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: Sea view, Fridge

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Price per night from

$753

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

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Price per night from

$3,603

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

1 of 2 match: Sea view, Fridge

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Price per night from

$1,596

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: Sea view, Fridge

1 of 2 filters match

Price per night from

$1,056

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Sea view, Fridge

1 of 2 filters match

Price per night from

$1,603

Great rentals within 20 miles that match your search

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

Honolulu house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Fridge Sea view

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Price per night from

$218

Match: Fridge Sea view

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Price per night from

$114

2 Adjoining Suites -- POSH AND LAVISH -- Direct Ocean Views

Honolulu apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Fridge Sea view

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Price per night from

$796

“Lovely apartment, lovely location” This was an excellent rental in every respect. The location is wonderful, the property owner is very nice, and the flat itself is comfortable and welcoming. I would recommend it without reservation.

Responds fast! avg. 2 hours 32 minutes

Match: Fridge Sea view

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Price per night from

$205

Ilikai Collection # 2. Beachfront Condo with ocean views from every room!

Honolulu apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

“Beautiful, clean, spacious condo with amazing views and location” My husband and I stayed in this condo with our 2 boys as well as his parents. We found that we had lots of room for all of us. The unobstructed views from the 2 lanais were absolutely beautiful. The pictures do not do it justice. The kitchen was well stocked and we had more than enough towels and linens. ( bring your own beach towel though or buy some for a souvenir) Our boys enjoyed using the snorkelling gear. The double beds were a touch hard for my tastes but comfortable enough. The location was perfect for us. The beach was within easy walking distance and we enjoyed swimming in the lagoon as well. I would absolutely recommend this condo, we would love to return! Thank you Dainora for a wonderful stay and ease of rental.

Responds fast! avg. 1 hour 47 minutes

Match: Fridge Sea view

All filters match

Price per night from

$853

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