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

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Condo Rentals in Kailua

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Swim with the Turtles - Bungalow close to Kailua Beach – Property 256803

  • Kailua rental - cottage, 1 bedroom, sleeps 4, 1 bathroom, near the ocean, town, pool
  • $650/week
  • Calendar Last Updated On: Nov 24, 2009
This 1 bedroom Cottage is surrounded all year by green and blooming tropical plants. The bedroom has a queen bed, ceiling fan and also a safe.The living room with...

8 BD/ 5 BA 2 Blocks to the Beach – Property 162641

  • Kailua rental - estate, 8 bedrooms, sleeps 22, 5 bathrooms, beach, mountain, pool
  • Calendar Last Updated On: Nov 24, 2009
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.

Available November/DEEP DISCOUNTS/ Pineapple Suite, Licensed B&B, close to beach – Property 250326

  • Kailua rental - studio, 1 bedroom, sleeps 3, 1 bathroom, beach, near the ocean, garden
  • $805/week
  • Calendar Last Updated On: Nov 24, 2009
Step back in time and soak up a peaceful, private, quintessential Hawaiian vacation experience. The Hula Breeze is a legal and licensed B&B located on a secluded...

Hale Hali'a Aloha in Kailua – Property 228621

  • Kailua rental - apartment, 1 bedroom, sleeps 3, 1 bathroom, near the ocean, waterfront, garden
  • $1,050/week
  • Calendar Last Updated On: Nov 23, 2009
Enjoy all the comforts of a high-end, island resort just steps from the bech in beautiful Kailua, and for half the cost! Our newly remodeled unit has its own...

Kailua Hawaiiana Home Right on the Beach – Property 266942

  • Kailua rental - house, 4 bedrooms, sleeps 10, 4 bathrooms, beach, waterfront, internet access
  • Calendar Last Updated On: Nov 23, 2009
Beachfront Hawaiiana home right on world famous Kailua Beach. This Hawaiiana beach house is the perfect place to relax and enjoy paradise.

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: Nov 23, 2009
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...

Beachside Paradise – Property 154516

  • Kailua rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, beach, garden
  • Calendar Last Updated On: Nov 22, 2009
This is a wonderful location, just three houses from the most beautiful beach in the world. The home offers complete privacy.

Available Dec.15th-22nd! Special rate for these dates: Short walk to beach – Property 255274

  • Kailua rental - studio, 1 bedroom, sleeps 3, beach, pool
  • $770/week
  • Calendar Last Updated On: Nov 24, 2009
Step back in time and soak up a peaceful, private, quintessential Hawaiian vacation experience. Romantic setting, ask about our honeymoon package. The Hula Breeze...

Resort-Like, Spa, Pool, Pool Cabana, 2 Min. Walk to Beach, Kailua-Lanikai – Property 266779

  • Kailua rental - house, 3 bedrooms, sleeps 7, 3 bathrooms, beach, mountain, pool
  • $2,765 - $3,325/week
  • Calendar Last Updated On: Nov 24, 2009
As you open the gate, you enter your own personal retreat, lush lawns, swaying palm trees, the soothing sound of water falls.

Hilltop Hale – Property 264283

  • Kailua rental - house, 2 bedrooms, sleeps 4, 1 bathroom, near the ocean, internet access
  • Calendar Last Updated On: Nov 20, 2009
The dramatic views of the ocean from the spacious outdoor deck, kitchen and living room are among the special features here at Hilltop Hale.

Wailea Lani - Most Luxurious Lanikai Living – Property 7016964

  • Kailua rental - house, 4 bedrooms, sleeps 9, 4 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 19, 2009
Fantasy 4 bedroom plus library, 4 bathroom celebrity vacation rental retreat in Lanikai. You will experience the most magical view of the Pacific Ocean, the Mokulua...

Hale Aloha – Property 7017031

  • Kailua rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, beach towels
  • Calendar Last Updated On: Nov 19, 2009
This Lanikai beachside vacation rental cottage is the ideal retreat for a couple or small family looking to relax in paradise.

Olu'olu House – Property 7017017

  • Kailua rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, books adult, books kids
  • Calendar Last Updated On: Nov 19, 2009
Better than beachfront! Recently built custom 4BR, 4 bath island style home just one house from Kailua Beach with private beach access.

Cottage at Lanikai – Property 7017029

  • Kailua rental - cottage, 2 bedrooms, sleeps 4, 1 bathroom, adventure, alarm clock
  • Calendar Last Updated On: Nov 19, 2009
Comfortable vacation rental cottage right in the center of beautiful Lanikai Beach on Oahu, Hawaii. Perfect for the ultimate family vacation or a reunion with...

Ho'o Nanea 210 – Property 264266

  • Kailua rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, near the ocean, satellite or cable
  • Calendar Last Updated On: Nov 19, 2009
This lovely island retreat is located just steps away from Kailua beach, rated #1 among the beaches in the world by Conde Nastescape.

Memorable Kailuana Beachfront Estate – Property 227708

  • Kailua rental - estate, 4 bedrooms, sleeps 12, 2 bathrooms, 1 half bath, beach, waterfront, air-conditioning
  • Calendar Last Updated On: Nov 17, 2009
FULLY LICENSED A Private and Gated Estate offers a simple pleasures of tranquility with the beauty of white sand Beach of Kailua.

Tropical Paradise -Affordable – Property 214589

  • Kailua rental - house, 2 bedrooms, sleeps 5, 1 bathroom, beach, garden
  • $1,750/week
  • Calendar Last Updated On: Nov 20, 2009
'Tropical Garden Paradise' is only steps from the beach and is very affordable. Hale Kai is a 1,000 square-foot, two-bedroom cottage, situated just steps from Kailua...

Stunning Kailua Oceanfront House with Beach Walk Right Outside – Property 221336

  • Kailua rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, resort, waterfront, pool
  • Calendar Last Updated On: Nov 16, 2009
Stunning house on the Kailua beach ocean in the Kaimalino area, beautifully maintained, exquisite garden in the pool area, very quiet and secluded neighborhood!

Island Hale - Charming and Quiet--Summer Special Pricing!!! – Property 193209

  • Kailua rental - studio, 1 bedroom, sleeps 2, 1 bathroom, beach, near the ocean, garden
  • $600/week
  • Calendar Last Updated On: Nov 17, 2009
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...

Kailua's Coconut Corner Vacation Rental, 700sq.ft., Full Kitchen, Near beach – Property 204626

  • Kailua rental - house, 1 bedroom, sleeps 5, 1 bathroom, beach, near the ocean, air-conditioning
  • Calendar Last Updated On: Nov 16, 2009
Experience the real Hawaii away from the tourist environment of Waikiki. This 'home away from home' is just a half-mile from Kailua beach.
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