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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Enjoy the real Hawaii, Kalama Kai cottage, 2 blocks to beach – Property 125963

  • Kailua rental - cottage, 1 bedroom, sleeps 4, 1 bathroom, beach, near the ocean, garden
  • $600/week
  • Calendar Last Updated On: Nov 8, 2009
Discover the real Hawaii, get away from the city and enjoy the beautiful Windward side of Oahu, which offers gorgeous private beaches, shops, restaurants, yet just...

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

  • Kailua rental - apartment, 1 bedroom, sleeps 3, 1 bathroom, air-conditioning, internet access
  • $750/week
  • Calendar Last Updated On: Nov 8, 2009
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...

Ocean Air Fabulous Studio Minutes to All of Kailua – Property 224184

  • Kailua rental - condo, sleeps 2, 1 bathroom, beach, downtown, air-conditioning
  • $664/week
  • Calendar Last Updated On: Nov 8, 2009
In beautiful Kailua Town on the windward side of Oahu. A cool quiet studio within walking distance to shops, restaurants, and a beautiful beach for swimming,...

Beautiful Studio, Walk to Beach, mountain view, special**$699/wk all inclusive. – Property 314931

  • Kailua rental - studio, 1 bedroom, sleeps 2, 1 bathroom, near the ocean, balcony
  • $536/week
  • Calendar Last Updated On: Nov 8, 2009
Aloha! Welcome to a tropical Hawaii vacation rental, an easy 5 min. walk to the beach, shopping and restaurants. **Enjoy the feeling of the Hawaii with the...

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 7, 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!

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

  • Kailua rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, beach, pool
  • $3,850 - $4,375/week
  • Calendar Last Updated On: Nov 7, 2009
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...

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 8, 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...

Happy Kailua Beach House 1/2 Block from Kalama Beach Park – Property 319362

  • Kailua rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, garden
  • Calendar Last Updated On: Nov 4, 2009
The Happy Kailua Beach House is located 1/2 block down from Kalama Beach Park; a small, clean local beach park which has showers, restrooms, and a nice grassy area...

Kailua Beach House – Property 89172

  • Kailua rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, children welcome, Outdoor Shower
  • Calendar Last Updated On: Nov 4, 2009
A feeling of vintage Hawaii in this comfortable 3 bedroom, 2 baths home located in a tropical garden setting just 3 minutes walk from Kailua Beach.

Hale Kea – Property 89600

  • Kailua rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, children welcome, heated pool
  • Calendar Last Updated On: Nov 4, 2009
Hale Kea is a sprawling, Hawaiian-style home designed for casual living and family entertainment.<br /> <br /> Located just steps from beautiful Kailua Beach, this...

Kai Nani Cottage – Property 89623

  • Kailua rental - cottage, 3 bedrooms, sleeps 6, 1 bathroom, children welcome, air-conditioning
  • Calendar Last Updated On: Nov 4, 2009
Kailua Beachside: Quaint beach cottage steps from Kailua Beach on a very large beautiful property, enclosed with all- around lava rock walls; 3 bedrooms, 1 and 1/2...

Hale Ohe Main Home and Cottage – Property 89610

  • Kailua rental - house, 5 bedrooms, sleeps 11, 3 bathrooms, children welcome, Outdoor Shower
  • Calendar Last Updated On: Nov 4, 2009
Kailua beach tropical gem. Relax in a spacious tropical home on a private street that is just steps to the world famous Kailua Beach and 20 minutes to Honolulu.

Kailua Beach House and Tradewinds Cottage – Property 89625

  • Kailua rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, children welcome, Outdoor Shower
  • Calendar Last Updated On: Nov 4, 2009
KAILUA BEACH HOUSE <br /> A feeling of vintage Hawaii in this comfortable 3 bedroom, 2 baths home located in a tropical garden setting just 3 minutes walk from...

Pineapple Beach House – Property 89629

  • Kailua rental - cabin, 3 bedrooms, sleeps 6, 2 bathrooms, balcony, Deck Furniture
  • Calendar Last Updated On: Nov 4, 2009
This Kailua Oahu home is available for a thirty day rental. This charming home has everything you need for your dream vacation.

Kailua Kahakai Hale Ali'i – Property 89626

  • Kailua rental - house, 4 bedrooms, sleeps 10, 2 bathrooms, coffee maker, toaster
  • Calendar Last Updated On: Nov 4, 2009
This beach house has just been remodeled and is a short walk to Kailua Beach. The lush large lot is private, quiet and very tropical.

Makana's Place 3 Bedroom home – Property 89642

  • Kailua rental - house, 3 bedrooms, sleeps 9, 2 bathrooms, balcony, Deck Furniture
  • Calendar Last Updated On: Nov 4, 2009
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is...

Tranquility – Property 86980

  • Kailua rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, clothes dryer, deck wood
  • Calendar Last Updated On: Nov 4, 2009
Enjoy Kailua Beach sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand...this home is tranquility in paradise.

Kumulani – Property 86976

  • Kailua rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, air-conditioning, beach
  • Calendar Last Updated On: Nov 4, 2009
Relax, enjoy the trade winds, slip into the gorgeous blue tile, solar heated, salt water swimming pool in your oh-so-private backyard.

Peacock – Property 89650

  • Kailua rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, air-conditioning, clothes dryer
  • Calendar Last Updated On: Nov 4, 2009
Nestled in the foothills of the Koolau mountains, this 4 bedroom home is the perfect family retreat. Recently renovated, the home includes designer fixtures, a...

Pikake Hale – Property 89651

  • Kailua rental - house, 5 bedrooms, sleeps 10, 4 bathrooms, alarm clock, bottled water
  • Calendar Last Updated On: Nov 4, 2009
Beautiful, private Hawaiiana home, located just 100 yards from the middle of world-class Kailua Beach. Enjoy beautiful sunrises and the soothing sounds of the ocean.
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