Vacation Rentals & Apartments in Kailua

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Responds fast! avg. 2 hours 7 minutes

Match: Iron Jacuzzi or hot tub

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Price per night from

$985

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

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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$753

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

Kailua house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$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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Price per night from

$1,596

These homes match some but not all of your filters. Clear all filters

Kailua Home w/Spectacular Views, Newly Renovated

Kailua house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 10

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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

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Price per night from

$319

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

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Price per night from

$273

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Price per night from

$185

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$171

Responds fast! avg. 2 hours 7 minutes

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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

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Price per night from

$172

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

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

“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

$234

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

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Price per night from

$223

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$223

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$656

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Price per night from

$2,373

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$3,603

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

$211

Living Aloha! Walk to Beach, Free Parking

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$154

Ilikai Marina 780 Ocean Front Corner 2 X the View!

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect modern condo with breathtaking views!” Our stay at # 780 couldn't have been better. The condo is just beautiful with everything you need right there. The location is fabulous, and Janna is the perfect owner/hostess. She answered all of our questions straight away, and was available at any time if we needed her. The decor is beautiful and clean, and the condo is equipped with everything you need, although with so many wonderful restaurants close by we hardly used the fully equipped kitchen. The views are to die for, with magnificent sunsets every night and front row seats for the Friday nights fireworks. We used the Ilikai Hotel Tour desk for booking our tours and there were passes for the hotel pool which we used when we didn't swim in the ocean. I would most definitely stay there again and have recommended it to my friends.

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Price per night from

$259

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Price per night from

$113

Waikiki Beach, Hawaii: One Bedroom, Two Bath Condo

Honolulu apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 28 minutes

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Price per night from

$257

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Price per night from

$456

Large Studio Courtyard at Bamboo w/full kitchen. Minimum 2 nights.

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 19 minutes

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Price per night from

$166

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Price per night from

$262

Waikiki Beach Tower! Direct Oceanfront!

Honolulu hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$199

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

Honolulu condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$199

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

Honolulu house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$3,993

Renovated Specious Studio with Great View

Honolulu apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$141

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Price per night from

$178

RENOVATED & SPACIOUS 798 SQ FT Ocean View Suite + Den, FREE PARKING

Honolulu hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$158

Oasis in Paradise

Aiea house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$343

Boutique hotel- great location in Waikiki!!

Kahala studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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Price per night from

$887

Waikiki Panoramic Oceanview Studio

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$88

WAIKIKI BANYAN CONDO -19 TH FLOOR -WALK TO BEACH

Honolulu condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$211

Viewing 38 of 53
rentals in Kailua

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