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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Driftwood Studio- Walk to Beach- SAVE 20% April-May stays $100/nt – Property 3544241

  • Kailua rental - studio, 1 bedroom, sleeps 2, 1 bathroom, Rural, Lawn / Garden
  • Calendar Last Updated On: Apr 18, 2014
This newly renovated studio is perfect for two. Located on a larger corner lot just 5 miles from the bustling town of Kailua and just a short stroll to the 5 mile...

Coconut Hideaway -Quiet, Spacious & Private Treetop Setting – Property 963616

  • Kailua rental - house, 1 bedroom, sleeps 4, 1 bathroom, 1 half bath, accept credit card, Lake, Mountain, Near The Ocean
  • Calendar Last Updated On: Apr 18, 2014
Brand new one bedroom, treetop location overlooking the world famous Mid Pacific Country Club Golf Course. Where Presidents play.

Tropical Hideaway Studio on the Water in Kailua with Swimming Pool – Property 913424

  • Kailua rental - studio, sleeps 4, 1 bathroom, accept credit card, wheelchair accessible
  • Calendar Last Updated On: Apr 18, 2014
This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool.

Palatial Oahu Lani - Beachfront, Ideal for Large Family or Corporate Retreat – Property 3586320

  • Kailua rental - villa, 10 bedrooms, sleeps 20, 10 bathrooms, Private Pool, Fitness Room / Equipment
  • $42,000 - $52,500/week
  • Calendar Last Updated On: Apr 18, 2014
Oahu Lani is a child-friendly, family-oriented beachfront villa that occupies a superb location on Kailua beach, rated one of the 10 finest beaches in the U.S.

Palatial Oahu Lani - Beachfront, Ideal for Large Family or Corporate Retreat – Property 3219195

  • Kailua rental - villa, 6 bedrooms, sleeps 12, 10 bathrooms, Private Pool, Fitness Room / Equipment
  • $36,400 - $52,500/week
  • Calendar Last Updated On: Apr 18, 2014
Oahu Lani is a child-friendly, family-oriented beachfront villa that occupies a superb location on Kailua beach, rated one of the 10 finest beaches in the U.S.

New Modern Island Style Beachside Apartment – Property 935604

  • Kailua rental - apartment, 2 bedrooms, sleeps 5, 1 bathroom, accept credit card, pets considered
  • $1,603 - $2,100/week
  • Calendar Last Updated On: Apr 17, 2014
This private 2 bedroom 1 bathroom apartment sleeps 4 adults or 5 person family and is within 200 meters to Kailua Beach Park.
SPECIAL OFFER! Spring in Hawaii $700 per night March 28 - May 21

Experience Complete Tranquility In Paradise – Property 3684689

  • Kailua rental - house, 8 bedrooms, sleeps 18, 4 bathrooms, Hot Tub, Private Pool
  • $4,900 - $6,300/week
  • Calendar Last Updated On: Apr 16, 2014
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu .

'E komo mai. Nou ka hale.' 'Come inside, the house is yours.' – Property 3007626

  • Kailua rental - house, 4 bedrooms, sleeps 7, 1 bathroom, accept credit card, Near The Ocean
  • $2,300/week
  • Calendar Last Updated On: Apr 16, 2014
This plantation style home is located 2.5 blocks from Kailua beach and 3 blocks to Kailua town. It has been renovated to have the open floor plan to provide a...

Kailua 700sf Studio Steps to Kailua Beach – Property 397149

  • Kailua rental - studio, sleeps 2, Beach, Near The Ocean, Jacuzzi
  • Calendar Last Updated On: Apr 16, 2014
You will not be disappointed arriving to this spacious, open, conveniently located Large Beautiful Studio. Surrounded by palm trees and rock wall for tropical...

Hale Moana : 3 minute (200 yard) walk to Kailua Beach – Property 201176

  • Kailua rental - studio, sleeps 2, 1 bathroom, accept credit card, Beach, Near The Ocean
  • Calendar Last Updated On: Apr 15, 2014
Hale Moana is a Non-Smoking studio nestled beneath two lovely shade trees with a 'treehouse' view. Our studio is cooled by refreshing island tradewinds and by the...

Treetop Studio on Beachside Lane - Ocean & Mountain Views! – Property 226822

  • Kailua rental - studio, sleeps 4, 1 bathroom, Mountain, Waterfront, Balcony
  • Calendar Last Updated On: Apr 15, 2014
Beautiful, romantic treetop studio with great all-around views of Ocean and Koolau Mountains on quiet beach lane. Steps to beautiful Kailua Beach. View gorgeous...

Modern Beach House On Pristine Kailua Beach- In Town & Surrounded by Nature – Property 3022107

  • Kailua rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, Beach, Near The Ocean, Town, Waterfront, Jacuzzi
  • $1,999 - $4,199/week
  • Calendar Last Updated On: Apr 17, 2014
The ultimate beach house! Modern and newly constructed, the Kailua Bay Beach House is nestled between the mountains and the beach.

Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed – Property 222948

  • Kailua rental - house, sleeps 3, 1 bathroom, accept credit card, Beach, Waterfront
  • $1,540/week
  • Calendar Last Updated On: Apr 17, 2014
Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the other faces the ocean.

Tropical Beach Hale, 1 bedroom, A/C, across street from beach access – Property 3008037

  • Kailua rental - studio, 1 bedroom, sleeps 3, 1 bathroom, accept credit card, Beach, Near The Ocean
  • $1,120 - $1,260/week
  • Calendar Last Updated On: Apr 13, 2014
Aloha, come and relax at our tropical Kailua home located in one of Kailua's finest neighborhoods. Kailua Beach hale is located across the street from the beach...

Elegant Studio-Cottage, Tropical Pool Spa Private Yard Kayaks, Beach 2 min/walk – Property 3011034

  • Kailua rental - studio, sleeps 2, 1 bathroom, accept credit card, Hot Tub
  • $1,295/week
  • Calendar Last Updated On: Apr 17, 2014
As you open the gate, you enter your own personal retreat, lush lawns, swaying palm trees, the soothing sound of water falls.

'Koi Palms Luxury Cottage' Short Walk to Kailua Beach – Property 241024

  • Kailua rental - cottage, 1 bedroom, sleeps 2, 1 bathroom, accept credit card, Near The Ocean
  • $1,120/week
  • Calendar Last Updated On: Apr 16, 2014
Come and enjoy our island home with us. Koi Palms is located within our gated property alongside our lovely Koi pond, in the quaint town of Kailua.

Resort-Like, Spa, Pool, Tropical yard, 2 Min. Walk to World-Famous Lanikai Beach – Property 266779

  • Kailua rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, accept credit card, Hot Tub
  • $3,675 - $4,165/week
  • Calendar Last Updated On: Apr 18, 2014
As you open the gate, you enter your own personal retreat, lush lawns, swaying palm trees, the soothing sound of water falls.

Oceanfront Villa Soluna - Fabulous Views, Contemporary Décor, Culinary Art s Delight! – Property 3586321

  • Kailua rental - villa, 5 bedrooms, sleeps 10, 4 bathrooms, wheelchair accessible, Fitness Room / Equipment
  • $18,200 - $20,300/week
  • Calendar Last Updated On: Apr 18, 2014
This gorgeous oceanfront property has 10,500 sq ft, double gate with semi-circular driveway, a beautiful re-landscaped garden with a new extensive, travertine...

Kailua Beach Front Estate with Pool and Beautiful Ocean Views – Property 193768

  • Kailua rental - estate, 8 bedrooms, sleeps 14, 4 bathrooms, 1 half bath, Beach, Waterfront, Private Pool
  • Calendar Last Updated On: Apr 11, 2014
This fine property is centered on a nearly 6 mile white sand beach, just 30 minutes from downtown Waikiki. This marvelous retreat is the rarest find in all Hawaii!
SPECIAL OFFER! STAY IN MAY SPECIAL !!! $200/NT FOR 6 May 1 - May 31

Glass Ball Hideaway - Easy walk to beach ! - Whale watch season through May – Property 965534

  • Kailua rental - house, 2 bedrooms, sleeps 6, 1 bathroom, Near The Ocean, Rural, Lawn / Garden
  • Calendar Last Updated On: Apr 11, 2014
You will feel right at home in this newly renovated Hawaiian style home. Open and spacious this house sits on a large corner lot just a 2 minute stroll to the...
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