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Kailua

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Vacation Rentals in Kailua, Oahu

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Kailua holiday rentals

Kailua is a town on the Windward Coast of Oahu in Hawaii. The coast in general is renowned as an area of outstanding natural beauty, and Kailua is a great place to see some spectacular sunrises. With some great beaches and a laidback lifestyle, Kailua is the ideal destination for a relaxed family holiday. And with a huge amount of self-catered accommodation available in the town, you can find a home from home in this idyllic island setting. A trip to Hawaii might not sound like a money saving holiday, but there are rental homes available to suit every budget, and free up cash to enjoy the rest of your family holiday.

What to do in Kailua

Kailua Beach Park will be the first stop for many tourists, and this amazing ocean beach is bound to take up a few days of your visit. Work on your tan, and admire the sea turtles which can be seen in the area. Also, watersports enthusiasts will love the opportunities provided by Kailua Beach, including kayaking, windsurfing, kiteboarding and scuba diving. All necessary equipment can be hired nearby for some unforgettable holiday experiences. Quite apart from exploring the rest of the Windward Coast and Oahu in general, you will also have to take a boat out to the Mokulua Islands, two small islands just off Oahu's coast which provide great surfing opportunities and slightly less crowded white sandy beaches.

Renting an apartment in Kailua

With a huge variety of family friendly rental homes available in and around Kailua, it is easy to find deals on luxurious apartment rentals. With rental costs starting from just £390 for apartments large enough to accommodate a family of four or more, it can work out much less expensive than booking hotel rooms for the entire family. Many of the apartments come with spectacular ocean views, as well as access to private pools, tennis courts and other facilities, so it will certainly not feel like a low cost option! The extra privacy and space that comes with a rented holiday property also means that they're great for kids - the youngest members of your family can run around and let off steam without you having to worry about them disturbing the neighbours!

 
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
Hawaii, Oahu, Kailua Holiday Rentals
Ohana Beach House
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
493 AUD - 718 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
Hale Manu
Slideshow
4.5 of 5 stars 13 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
600 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
The Cottage at Kailua Beach Park
Slideshow
4.5 of 5 stars 5 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Professional
EMAIL AGENT
Night:
708 AUD - 872 AUD
Week:
4,957 AUD - 6,106 AUD
Month:
15,394 AUD - 18,473 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
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Sharon's...
92 AUD / night
3 Bedrooms, sleeps 9
3 Bathrooms
5 minutes from...
77 AUD - 272 AUD / night
7 Bedrooms, sleeps 22
5 Bathrooms
Peaceful...
128 AUD - 867 AUD / night
5 Bedrooms, sleeps 10
5 Bathrooms
Kailua...
200 AUD / night
1 Bedroom, sleeps 2
1 Bathroom
Bali Nani
1,232 AUD / night
6 Bedrooms, sleeps 4
3 Bathrooms
Hawaii, Oahu, Kailua Holiday Rentals
Aloha Spirit
Slideshow
4 of 5 stars 6 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
564 AUD - 795 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
Kona Pacific E-633
Slideshow
4 of 5 stars 6 reviews
  • Condo/Apartment
  • 1 Bedroom, sleeps 2
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
87 AUD - 144 AUD
Week:
611 AUD - 1,006 AUD
Month:
2,617 AUD - 2,771 AUD
Minimum rental - 3 nights
Check availability
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Hawaii, Oahu, Kailua Holiday Rentals
Exec Eco Friendly Beachside Home w/ Swimming Pool
Slideshow
4.5 of 5 stars 17 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
713 AUD - 816 AUD
Week:
4,921 AUD - 5,639 AUD
Month:
15,394 AUD - 18,473 AUD
Minimum rental - 5 nights
Check availability
Show on map
Hawaii, Oahu, Kailua Holiday Rentals
Oahu Lani, Hawaii
Slideshow
4 of 5 stars 1 review
  • Villa
  • 10 Bedrooms, sleeps 18
  • 11 Bathrooms
  • Professional
EMAIL AGENT
Week:
37,356 AUD - 53,879 AUD
Minimum rental - 1 week
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
5 minutes walk to Kailua Beach -Kailua Hale Ohana
4.5 of 5 stars 10 reviews
  • Holiday Rental House
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
97 AUD - 101 AUD
Week:
647 AUD - 677 AUD
Month:
2,053 AUD - 2,258 AUD
Minimum rental - 1 night
Check availability
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Hawaii, Oahu, Kailua Holiday Rentals
WOW LOOK Just 100 Steps off Kailua Beach
Slideshow
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
872 AUD
Week:
6,106 AUD
Minimum rental - 30 nights
Check availability
Show on map
Hawaii, Oahu, Kailua Holiday Rentals
Fabulous Views From Hawaii Beachfront Lanikai Home
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 5 Bedrooms, sleeps 8
  • 7 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
1,539 AUD
Week:
8,723 AUD
Minimum rental - 30 nights
Check availability
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Hawaii, Oahu, Kailua Holiday Rentals
BeachFRONT home with the best views on the island
Slideshow
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Owner
EMAIL OWNER
Night:
1,078 AUD
Week:
7,543 AUD - 10,776 AUD
Month:
21,552 AUD - 33,754 AUD
Minimum rental - 1 week
Check availability
Show on map
Hawaii, Oahu, Kailua Holiday Rentals
Ohana Beach House
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
493 AUD - 718 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
Hawaiian Plantation Style Studio Cabana
Slideshow
4.5 of 5 stars 5 reviews
  • Holiday Rental House
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
190 AUD
Minimum rental - 3 nights
Check availability
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Hawaii, Oahu, Kailua Holiday Rentals
Makana's Place 3 Bedroom home
Slideshow
4 of 5 stars 8 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
303 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
Hale Kimo
Slideshow
4.5 of 5 stars 7 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
770 AUD - 872 AUD
Month:
19,627 AUD
Minimum rental - 2 nights
Check availability
Map unavailable
Hawaii, Oahu, Kailua Holiday Rentals
Beautiful Beach Villa w/ Swimming Pool & Jacuzzi
Slideshow
4.5 of 5 stars 12 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 7
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
405 AUD - 508 AUD
Week:
2,838 AUD - 3,556 AUD
Month:
10,776 AUD - 12,315 AUD
Minimum rental - 3 nights
Check availability
Show on map

Kailua Holiday Rental Advice

large vacation rental
Posted by swmarket, 24 Jun 2011
... all the details and permits. She's certainly not a legal rental if that matter to you. I'd be concerned since one of her sites says that "we can only rent it for a week each month"............smells like they've already had trouble with neighbors about vacation rental ... more
Posted by amberloo, 24 Jun 2011
... get around the laws against vacation rentals on ... ... a home out as a vacation rental up to 12 times each year without breaking any laws; whether for a day, week or month at a time. In theory, a place can't be rented out more than once during each 30 ... more
Posted by swmarket, 24 Jun 2011
... not a permitted or licensed vacation rental instead, and that they are using a loophole to work around the lack of a permit. But my goal here was really to try and show Boxer that research is easy and a good thing. I don't know that this property is ... more
Kailua / Windward beaches = Windy?
Posted by KailuaMama, 13 Jan 2012
... are unaware of the illegal vacation rental situation here and really can't be held responsible. Others simply don't care. Not going to bother posting links but if you're interested in reading more about it you can google "oahu illegal vacation rentals." The controversy has been going on ... more
House rental being given away as a prize. Legal or illegal?
Posted by LUFCkev, 5 Jan 2012
... that the vast majority of vacation rentals in this area are illegal. Also, despite the competition being 100% legitimate, there's a free online entry route, but also a method of entry where you get extra entries through a premium rate text/phone call. I'd hate to enter, win ... more
Posted by msfuzz, 6 Jan 2012
epi, this year Obama did rent a legally permitted vacation rental in Kailua!! ... more
Posted by amberloo, 6 Jan 2012
... the owner requires one-month vacation rentals, plays the "Obama" game, or just doesn't rent it out more than once a month or twelve times a year, the County really can't touch them. However, there has long been talk of closing this loophole. They couldn't just change ... more
Kailua Legal Rentals
Posted by amberloo, 9 Jun 2011
... using the property as a vacation rental and are in compliance with the regulations, there is no reason to think there will be any changes in the approved roster. I have not heard a single peep from anybody or any agency on any side of the issue which has expressed ... more
Kailua Town -- 'nightlife'?
Posted by KDaph81, 21 Sep 2010
... fully understand the legal/illegal vacation rental dilemma but hope we're OK.) However, we would like to go out and about and have a drink or two, maybe hear some live music; in general be around other people, but nothing crazy or late-night. Any suggestions of where and ... more
Week in Kailua -- should we or shouldn't we?
Posted by TigersFan2, 11 Aug 2010
... we finally decided on the vacation rental we wanted. Then I came across some very disturbing information. Apparently most vacation rentals in Kailua are "illegal" (i.e., non-permitted). And most Kailua residents seem to hate them (and perhaps the visitors). While I understand that we probably don't have ... more