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Kailua Vacation Rentals

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Kailua Vacation Rentals

About Kailua

127 apartments

Open Air Loft, Steps from beach

Kailua apartment

1 bedroom / 1 bathroom / Sleeps 2

$189

1 / 16

Affordable Place on the Best Beach in Hawaii

Kailua house

1 bedroom / 1 bathroom / Sleeps 2

$141

1 / 18

Perfect Oasis, Steps to the Beach! 100% Solar!

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 2

$178

1 / 14

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 2

$80

1 / 32

Holiday Palms - Private -5 min from Kailua beach

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 5

$129

1 / 12

Garden of Dreams - swimming pool on property -

Kailua studio

Studio / 1 bathroom / Sleeps 2

$87

1 / 21

ON BEAUTIFUL KAILUA BEACH

Kailua villa

1 bedroom / 1 bathroom / Sleeps 4

$195

1 / 16

Nancy's Kailua Cottage Mauka

Kailua cottage

/ 1 bathroom / Sleeps 4

“Nancy's is the perfect place to get away from the hustle of Honolulu!” My wife and I recently stayed at Nancy's while on Oahu. It's a short hop across the island in Kailua, about a 20-30 minute drive from Honolulu. The cottage has everything you need,

$80

1 / 15

Kailua Beach Aloha Cottage

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 4

$168

1 / 13

Martins Hale

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 3

$194

1 / 15

Kailua Beach Cottage 2BD/2BA walk to the beach!

Kailua condo

2 bedrooms / 2 bathrooms / Sleeps 4

“Perfect Hawaiian Getaway” We had an absolutely wonderful Hawaiian vacation! This Kailua cottage was perfect for our family of four, with hosts who welcomed us with that incredibly warm Hawaiian hospitality! We were given great information on local r

$249

1 / 23

$133

1 / 7

Beachfront Plantation Cottage

Kailua house

3 bedrooms / 2 bathrooms / Sleeps 6

$492

1 / 23

Charming 1 bedroom house

Kailua house

1 bedroom / 1 bathroom / Sleeps 2

“Convenient” The house was convenient to everything we wanted to do and see while in Oahu. It was very comfortable, clean, and the owner was easily accessible. We would stay there again.

$144

1 / 12

Best Location in Kailua! D&D's Cottage

Kailua cottage

1 bedroom / 1 bathroom / Sleeps 2

$112

1 / 15

Cozy Cottage 5 Minute Walk to Kailua Beach

Kailua house

1 bedroom / 1 bathroom / Sleeps 4

$125

1 / 13

Tropical Kailua Studio on the Water w/Private Pool

Kailua house

/ 1 bathroom / Sleeps 5

$100

1 / 12

Kailua by the Sea Studio

Kailua room

1 bedroom / 1 bathroom / Sleeps 2

$171

1 / 25

NEW! 3BR Island House 5 Min. From Kailua Beach!

Kailua house

3 bedrooms / 1 bathroom / Sleeps 5

$179

1 / 24

SUITE ALOHA – Remodeled, Romantic Island Retreat

Kailua house

1 bedroom / 1 bathroom / Sleeps 2

“"Lovely"” We stayed at Suite Aloha in September for 11 days. The room was spacious, airy and very comfortable. There was a huge ceiling fan to cool the entire room throughout the day and night. We were awakened by the sweet fragrance of plumeria a

$126

1 / 36

Lovely 2 Bedrooms Homeaway in Kailua Beach Town

Kailua house

2 bedrooms / 1 bathroom / Sleeps 6

$177

1 / 23

Sheffield Suite open: 4/21-26, 5/5-9, 5/19-23,5/30-6/8, 6/13-7/8, more

Kailua b and b

1 bedroom / 1 bathroom / Sleeps 3

$153

1 / 13

Kailua, Cozy, Spacious Duplex Home

Kailua house

1 bedroom / 1 bathroom / Sleeps 3

$149

1 / 23

Royal Kailua Estate

Kailua villa

8 bedrooms / 10 bathrooms / Sleeps 16

$9,500

1 / 37

Lanikai Cottage

Kailua house

2 bedrooms / 2 bathrooms / Sleeps 4

$348

1 / 13

Kaapuni Kainani

Kailua house

3 bedrooms / 3 bathrooms / Sleeps 8

$596

1 / 21

Ginger studio, private entry/bathroom, near beach

Kailua studio

Studio / 1 bathroom / Sleeps 2

$90

1 / 12

Lanikai Cottage

Kailua house

3 bedrooms / 2 bathrooms / Sleeps 8

$600

1 / 27

The quaint Kailua-Kalama "Cottage"

Kailua cottage

/ 1 bathroom / Sleeps 2

$105

1 / 10

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / Sleeps 7

$425

1 / 30

Stunning Estate Owned by Paul Mitchell on Lanikai Beach on Oahu!

Kailua villa

7 bedrooms / 7 bathrooms / Sleeps 14

$7,500

1 / 39

On Beautiful Kailua Beach

Kailua condo

3 bedrooms / 3 bathrooms / Sleeps 8

$422

1 / 26

Kailua, Cozy, 2 bedroom, Duplex Home

Kailua house

2 bedrooms / 1 bathroom / Sleeps 4

$165

1 / 29

Shangri La By The Sea

Kailua house

5 bedrooms / 3 bathrooms / Sleeps 10

$894

1 / 20

42 feet from Beautiful Kailua Beach Wonderful 4 Bedroom Home Lots of Extra's

Kailua house

4 bedrooms / 4 bathrooms / Sleeps 8

“Best Beach Front Home Yet” We've stayed at several beach front homes in Hawaii and California and this one was our favorite. The layout is perfect for families, the view was awesome, and Kailua Beach is one of our favorite beaches. We also loved the

$993

1 / 75

ON BEAUTIFUL KAILUA BEACH

Kailua house

1 bedroom / 1 bathroom / Sleeps 2

$172

1 / 16

“You will be very happy you stayed here” We are very experienced travelers and also rent our vacation home so have a perspective on both sides of this equation. We are a family of four with two teenage daughters (ages 14 and 13 at time of the stay).

$194

1 / 62

Castle Point Estate

Kailua house

7 bedrooms / 8 bathrooms / Sleeps 15

$9,500

1 / 44
Viewing 38 of 127

About Kailua

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Just a quick drive from the capital of Honolulu and Waikiki Beach, the small coastal town of Kailua is one of Hawaii's most picturesque and accessible beach communities. Overlooking the expansive, sapphire blue Kailua Bay, the town is bordered by a gorgeous white sand beach, often ranked among the best in Hawaii. Bring your book, a beach towel, and a pair of flip flops; you don't need much more to enjoy life in Kailua.

With continuous trade winds rolling off the coast, the climate is always comfortable in sunny Kailua, Hawaii. Thanks to the steady breeze, it is also a great spot for windsurfing and other beach activities, like horseback riding, swimming, kayaking, and snorkeling. If you want to explore the tropical scenery around Kailua, there are also tons of hiking trails in the surrounding Koolau Ridge and the Ka Iwi Ridge.

Here are a few additional suggestions of things to do in Kailua:

  • Kailua Beach Park: An uninterrupted two-mile stretch of white sand and blue sea, Kailua Beach has been repeatedly named one of Hawaii's best beaches.
  • Lanikai: Just outside Kailua, the small community of Lanikai is home to another incredibly beautiful stretch of sand.
  • Honolulu and Waikiki: If you visit Kailua, don't overlook its famous neighbor, the fun capital city of Honolulu.
  • Ka'iwa Ridge Trail: Spend a few hours ascending the Ka'iwa Ridge for fabulous views of Kailua Bay below.
  • Kawainui Marsh: Just outside Kailua, Hawaii's largest wetland and freshwater lagoon is a wonderful place to observe unusual birds and vegetation.
  • Ulupo Heiau State Historic Site: This historic Hawaiian temple was built in the 18th century and is believed to be the former home of several Oahu chiefs.

If you are coming to stay on this piece of paradise, look for a comfortable vacation rental for the family or a luxury villa with ocean views for a romantic getaway. You can also find a condo or apartment for rent, often within walking distance of the waves.

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