Kailua Offers a Change of Pace

A breath of fresh air even by Hawaiian standards, Kailua will quietly and expertly meet your vacation needs. Just twenty minutes from the airport, this beach town is welcoming and rich with diversions but stops far short of being crowded or overwhelming; it’s the perfect balance for anyone who likes to escape from reality without giving up the modern amenities and scenic beauty of a well-rounded getaway.


Kailua Beach is considered one of Oahu’s finest, boasting white sand, gentle hazard-free slopes and perfect conditions for wind and body surfing. Lanikai Beach is a smaller spot that is so stunning it often serves as the backdrop for photo shoots, probably explaining why it can become a little crowded at times.


Kailua is located just 15 minutes from Honolulu on the other side of the Koolau Mountains, so the drive from the big city entails going through a tunnel on the Pali Highway and emerging triumphantly into the sunshine. This moment of clarity will start your vacation off on the right foot, and the momentum will surely continue until the very end. Vacation houses and beach cottages take center stage here, and will further enhance the low-key experience of venturing from the beaten path and discovering a more authentic Hawaii than most people ever do.


By now you’ve surely realized that Kailua is the place for you, so get ready to let the trade winds carry you to a better place.

Destination: Search

Condo Rentals in Kailua

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Island Hale - Holiday Pricing!!! – Property 193209

  • Kailua rental - apartment, 1 bedroom, sleeps 2, 1 bathroom, beach, near the ocean, accept credit card
  • $550 - $600/week
  • Calendar Last Updated On: Dec 4, 2008
Island Vacation Hale. Our Island Hale is located on a quiet, Kamaaina street in one of Kailua’s finest neighborhoods. With its own gated private entrance, our...

Affordable, Private and Convenient - Golf Course View, Pool – Property 169982

  • Kailua rental - house, 4 bedrooms, sleeps 8, 2 bathrooms, near the ocean, swimming pool
  • Calendar Last Updated On: Dec 3, 2008
Come and enjoy our tropical oasis. Nearby Kailua beaches are some of the best in the world. After swimming with the turtles at the beach, come and swim with the...

Winter Special - 4 bed 2 bath, 2 living rooms, very large house, A/C – Property 140988

  • Kailua rental - house, 4 bedrooms, sleeps 10, 2 bathrooms, near the ocean, accept credit card
  • $1,225 - $2,030/week
  • Calendar Last Updated On: Dec 2, 2008
Very large four bedroom with two Living rooms, 1 full kitchen and one partial kitchen, 2 full bathrooms and beautiful garden.

Come and Experience the 'House of Sweet Dreams' Kailua Beach – Property 149302

  • Kailua rental - apartment, 1 bedroom, sleeps 3, 1 bathroom, air-conditioning, washing machine
  • Calendar Last Updated On: Dec 4, 2008
Hale O KuhiKuhi HiHi' O -- 'Ha Lay O Coo Hee Coo Hee Hee Hee O' Aloha and Welcome to the 'House of Sweet Dreams'. If you were able to pronounce the name of our...

4 bedroom 2 bath Jacuzzi and A/C – Property 313941

  • Kailua rental - house, 3 bedrooms, sleeps 10, 2 bathrooms, near the ocean, accept credit card
  • $1,575 - $2,030/week
  • Calendar Last Updated On: Dec 2, 2008
Aloha and welcome to this comfortable four bedroom two bath property with 4th bedroom and 2nd bath in seperate studio with hot tub outside.

Clay Art Rental – Property 150806

  • Kailua rental - cottage, 1 bedroom, sleeps 5, 1 bathroom, air-conditioning, washing machine
  • Calendar Last Updated On: Dec 1, 2008
This vacation rental is a self-contained building adjacent to a clay artist studio and home. It is 658 square feet in size and is located on a 9000 square foot lot.

8 BD Estate 2 Blocks to the Beach- See Current JAN/FEB Special rate! – Property 162641

  • Kailua rental - estate, 8 bedrooms, sleeps 22, 5 bathrooms, beach, mountain, accept credit card
  • Calendar Last Updated On: Dec 4, 2008
Our resort style home is the ideal spot for large gatherings and reunions. It's open, spacious, free flowing floor plan makes it perfect for entertaining.

Quality 1 Bedroom Apartment with Full Kitchen 2 Minutes Walk from Kailua Beach – Property 314192

  • Kailua rental - apartment, 1 bedroom, sleeps 4, 1 bathroom,
  • Calendar Last Updated On: Dec 1, 2008
This 1 bedroom 600+ sq. ft suite is a brand new, first class suite. With a queen size bed in the bedroom and a queen size sofa bed in the livng room, the suite...

Mountain Views, Wi-Fi, 3 miles to Kailua Beach – Property 208360

  • Kailua rental - studio, sleeps 3, 1 bathroom, accept credit card, air-conditioning
  • $700/week
  • Calendar Last Updated On: Nov 30, 2008
Your 'Home Away From Home'.Welcome. Enjoy a comfortable sleep on a King Size Bed. We also have a Futon Couch that opens to a Full-Size Bed. Air Conditioned, 2...

Kailua Lani - Private Street/Beach Access-Private Pool – Property 219313

  • Kailua rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, swimming pool
  • $3,850/week
  • Calendar Last Updated On: Nov 30, 2008
Enjoy the Aloha spirit at Kailua Lani. Our fully furnished 2800 sq. ft. home is a mere 50 steps to Kailua Beach, which has been rated as one of the top ten most...

Enchanted Kailua Ocean View, Sleeps 10 – Property 190517

  • Kailua rental - house, 3 bedrooms, sleeps 10, 2 bathrooms, near the ocean, accept credit card
  • Calendar Last Updated On: Nov 29, 2008
Enchanted Kailua Ocean View is a spacious 3 Bedroom 2 Full Bath property with a wrap around Lanai that is very reasonably priced.

Beautiful, Modern Beachside Villas with Fully Tiled Swimming Pools, Jacuzzis – Property 305308

  • Kailua rental - house, 5 bedrooms, sleeps 11, 5 bathrooms, beach, near the ocean, accept credit card
  • $1,295/week
  • Calendar Last Updated On: Nov 29, 2008
Beautiful Kailua Beachside Villas and cottages, each with a semi-private swimming pool and Jacuzzi in a very private tropical setting. Surrounded with lush tropical...

Paradise for Rent - 'Kahela' – Property 212457

  • Kailua rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, beach, near the ocean, swimming pool
  • Calendar Last Updated On: Nov 26, 2008
Located just steps from the best part of Kailua Beach. The beach is a three minute walk through Kailua Beach Park where the waves are the most gentle, the sand is...

'Hale O' Aloha' a Romantic Getaway for Two in Kailua, Hi. – Property 166379

  • Kailua rental - studio, sleeps 2, near the ocean, swimming pool
  • $625 - $675/week
  • Calendar Last Updated On: Nov 25, 2008
You will stay in a private, relaxing room upstairs in the main house. You will have your own entrance and key. The room has a queen bed, cathedral ceilings, hardwood...

Charming Cottage on Private, Gated Estate – Property 187225

  • Kailua rental - cottage, 1 bedroom, sleeps 2, 1 bathroom, mountain, near the ocean, accept credit card
  • Calendar Last Updated On: Nov 25, 2008
A pretty little cottage with a queen size bed, fine linens, and porcelain tile floors. The private bath with a tiled shower has a hair dryer, lots of fluffy towels...

Private Estate's West Wing with Pool – Property 187234

  • Kailua rental - estate, 2 bedrooms, sleeps 4, 2 bathrooms, swimming pool, air-conditioning
  • Calendar Last Updated On: Nov 25, 2008
E Komo Mai - Welcome! Indulge yourself in large, luxurious suites - a perfect setting to enjoy the hospitality of old Hawaii in this gracious, kama'aina home, near...

Active Families Love This Home: Close to the Beach - with Pool, and Spa – Property 207816

  • Kailua rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, accept credit card
  • $2,772 - $3,402/week
  • Calendar Last Updated On: Nov 29, 2008
WELL EQUIPPED, Well Appointed, Private, Luxurious, Exceptionally Comfortable, & Eco Friendly, this walk to Kailua beach, House will create memories that will last a...

Stunning Kailua oceanfront house with beach walk right outside – Property 221336

  • Kailua rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, resort, waterfront, swimming pool
  • Calendar Last Updated On: Nov 24, 2008
Stunning house on the Kailua beach ocean in the Kaimalino area, beautifully maintained, exquisite garden in the pool area, very quiet and secluded neighborhood.

Enchanted Lakes Villa – Property 176730

  • Kailua rental - house, sleeps 4, 1 bathroom, near the ocean, town, accept credit card
  • Calendar Last Updated On: Nov 22, 2008
Do you want to get out of the hustle and bustle of Waikiki, but still find an affordable place to stay? Then my home is your 'vacation' home, please come on in!

Spacious 1,000ft Air Conditioned Apartment Only 300 Yards from Beautiful Kailua – Property 308795

  • Kailua rental - apartment, 2 bedrooms, sleeps 5, 1 bathroom, beach, near the ocean, accept credit card
  • Calendar Last Updated On: Nov 22, 2008
Walk across the road to the white sand and turquoise water of beautiful Kailua Beach! Shut the door of your spacious bedroom/sitting room and let the kids or others...
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