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Vacation Rentals & Apartments in Kailua

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341 apartments

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 41 minutes

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$96

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$211

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

/ 1 bathroom / sleeps 2

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Price per night from

$165

Lovely 2 Bedrooms Homeaway in Kailua Beach Town

Kailua house

2 bedrooms / 1 bathroom / sleeps 6

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$210

Nancy's Kailua Cottage Mauka

Kailua cottage

/ 1 bathroom / sleeps 4

“Nancy's is the perfect place to get away from the hustle of Honolulu!” My wife and I recently stayed at Nancy's while on Oahu. It's a short hop across the island in Kailua, about a 20-30 minute drive from Honolulu. The cottage has everything you need, great bed, nicely appointed full kitchen, available barbeque and bicycles, some picnic supplies, you name it! There is a nice lanai out from which to relax, read, or just stare off to the distant mountains. Rick, one of the owners, is very friendly and extremely knowledgeable about Oahu and the other islands. He directed us to a tide pool area (Better be in some kind of shape!), a local hiking trail (ditto), and had all sorts of information available. The cottage is a short walk from a beautiful beach (almost a cliché in Hawaii), and a very short drive to the town's commercial area, which has several grocery stores and a selection of reasonably priced restaurants if you're tired of cooking. All in all, a great place to stay and relax!

Responds fast! avg. 41 minutes

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$98

Beachfront Kailua, Oahu

Kailua house

2 bedrooms / 2 bathrooms / sleeps 6

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$528

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

1 bedroom / 1 bathroom / sleeps 3

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$194

Hale Mokulua ~ with private pool & spa~steps to Lanikai Beach~3 living spaces

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

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$2,571

Oahu Apartment w/ Patio - Steps to Kailua Beach!

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 25 minutes

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$142

Kailua Beachfront~private~newly renovated home w/stunning views

Kailua house

3 bedrooms / 2 bathrooms / sleeps 8

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$2,571

Great Location - Very Clean - 1 Bedroom

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

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$177

E Komo Mai Private Bedroom near Kailua Beach Town

Kailua house

1 bedroom / 1 bathroom / sleeps 4

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$159

Kehaulani - Lanikai~ Stunning Ocean Views~ private residence

Kailua house

4 bedrooms / 4 bathrooms / sleeps 10

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$1,786

Walker's Lanikai Beach House~Oceanfront restored Historic home

Kailua house

5 bedrooms / 4 bathrooms / sleeps 14

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$1,500

Mokulua Aina~Lanikai tropical retreat with pool ~ steps to Lanikai Beach

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

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$1,786

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

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!

Responds fast! avg. 2 hours 40 minutes

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$230

SUITE ALOHA – Remodeled, Romantic Island Retreat

Kailua house

1 bedroom / 1 bathroom / sleeps 2

“"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!

Responds fast! avg. 1 hour 28 minutes

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$165

Comfortable house right on sandy part of Lanikai

Kailua house

2 bedrooms / 2 bathrooms / sleeps 6

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$412

Perfect Beachtown Retreat

Kailua house

1 bedroom / 1 bathroom / sleeps 4

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$124

Cozy Beachtown Getaway

Kailua apartment

1 bedroom / 1 bathroom / sleeps 2

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$106

Bright Kailua House w/Pool & Patio by Beaches

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 31 minutes

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$197

Kailua Beach House

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

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$1,256

Lanikai Oceanside 5 Bedroom

Kailua house

5 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$2,010

Ke'aloha

Kailua apartment

4 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$588

Lanikai Ocean View Villa

Kailua house

4 bedrooms / 3 bathrooms / sleeps 8

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$1,457

Large Private Luxury Home w/Pool, A/C and Ocean Views. Kailua Shores Estate

Kailua apartment

5 bedrooms / 5 bathrooms / sleeps 10

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$4,020

Lanikai Breeze

Kailua house

5 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$1,508

Lanikai Oceanside 4 Bedroom - Lanikai Kailua Oceanfront Beach House

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,759

Hale Kimo

Kailua villa

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$905

Tropical Kailua Studio - 3-Minute Walk to Beach!

Kailua studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 29 minutes

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Price per night from

$119

Ocean Breeze~Oceanfront on Kailua Bay~Spectacular Views, beautiful sunrise

Kailua house

4 bedrooms / 3 bathrooms / sleeps 8

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$1,500

Your Private Place in Paradise - Sleeps 2 to 4!

Kailua apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 27 minutes

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$170

Place in Paradise~Kailua Beach Front ~ Large private home sleeps up to 14.

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

“INCREDIBLE!” Best vacation home in Kailua (possibly the world)! The house itself has everything you need and is spacious and luxurious. The location is second to none, with one of the best best beaches right on your doorstep. Great option for families and large groups who like a bit of space. The property manager is a legend and makes the best bread pudding on the planet. If you're after a vacation/holiday to remember, this is it! Highly, highy recommend. Cheers, Johno.

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$1,500

Kailua, Entire 3 Bedroom Home, carport, yard, BBQ

Kailua house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 48 minutes

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Price per night from

$340

White Sands Escape by the Beach

Kailua house

1 bedroom / 1 bathroom / sleeps 1

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Price per night from

$76

Great rentals within 20 miles that match your search

Ala Moana Condo - 1 Bdrm Ocean View - 24th Fl. !

Honolulu condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$245

Floating accommodation in Paradise and cruises included

Honolulu yacht

3 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$666

"Maui Wowie" - 2018 Hymer Campervan RV

Kahului camper van

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$268

Viewing 38 of 341
rentals in Kailua

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