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Vacation Rentals & Apartments in Kailua

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Vacation Rentals & Apartments in Kailua

About Kailua

1,567 apartments

Kailua Guesthouse with Pool and Views!

Kailua cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 22 minutes

Price per night from

$425

1 / 24

Kailua, Cozy, 2 bedroom, Duplex Home

Kailua house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 40 minutes

Price per night from

$165

1 / 29

Kailua Beach Hideaway, SPACIOUS 1b/1b, minutes to World Famous Kailua Beach

Kailua apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$165

1 / 23

Holiday Palms - Private -5 min from Kailua beach

Kailua cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 49 minutes

Price per night from

$130

1 / 12

Open Air Loft, Steps from beach

Kailua apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 45 minutes

Price per night from

$190

1 / 16

Tropical Kailua Studio on the Water w/Private Pool

Kailua house

/ 1 bathroom / sleeps 5

Price per night from

$149

1 / 12

Nice cozy studio3, Enchanted Lake Kailua

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$70

1 / 6

Tranquil Tropical Beach Retreat

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 4 minutes

Price per night from

$250

1 / 33

Tropical Garden Studio - Free Wifi

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 50 minutes

Price per night from

$97

1 / 17

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

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

“Great cottage in best part of Kailua” We live in Kauai and periodically come to Oahu to visit friends or to for medical appointments. For a recent 4-night trip, we decided to stay in a vacation rental rather than a hotel; we chose Kailua because the b

Responds fast! avg. 3 hours 38 minutes

Price per night from

$179

1 / 14

Kailua, Cozy, Spacious Duplex Home

Kailua house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 40 minutes

Price per night from

$150

1 / 23

Kailua by the Sea Studio

Kailua room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$172

1 / 25

Cute Beachwalk Bungalow

Kailua cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 50 minutes

Price per night from

$136

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NEW! Tropical Kailua Studio Close To Beach!

Kailua studio

Studio / 1 bathroom / sleeps 3

Responds fast! avg. 24 minutes

Price per night from

$126

1 / 24

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$80

1 / 32

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

Responds fast! avg. 2 hours 23 minutes

Price per night from

$126

1 / 36

Ginger studio, private entry/bathroom, near beach

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$90

1 / 12

Hale Mokulua

Kailua villa

5 bedrooms / 5 bathrooms / sleeps 14

Responds fast! avg. 1 hour 6 minutes

Price per night from

$3,800

1 / 37

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 35 minutes

Price per night from

$425

1 / 30

Cozy Cottage 5 Minute Walk to Kailua Beach

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$125

1 / 13

Affordable Place on the Best Beach in Hawaii

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 14 minutes

Price per night from

$142

1 / 18

Luxurious 4 BR Kailua Home, Air-Conditioning, Short walk to Beach, Pool!

Kailua house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 31 minutes

Price per night from

$599

1 / 35

Hale Ohana steps to Kailua Beach

Kailua house

1 bedroom / 1 bathroom / sleeps 2

“Amazing holiday place to stay!!!” We have rented Tina's apartment twice now from sydney australia and plan on returning yearly. The location is right across the road from the most beautiful beach in Hawaii. Tina is an amazing host making sure the r

Responds fast! avg. 3 hours 44 minutes

Price per night from

$125

1 / 15

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

Price per night from

$159

1 / 13

NEW! Cozy 1BR Kailua Apartment Steps To Beach!

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 24 minutes

Price per night from

$154

1 / 24

Plantation at Paradise Point

Kailua villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 6 minutes

Price per night from

$4,500

1 / 26

Serenity Beachfront Cottage

Kailua house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$349

1 / 8

Lanikai Cottage

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$350

1 / 13

Price per night from

$134

1 / 7

4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach

Kailua house

4 bedrooms / 2 bathrooms / sleeps 8

“Go when want be a householder of HAWAII!!” Parents & kids were enjoyed to stay and we felt we lives in Hawaii. Everything was perfect but one thing we didn't like is blunt knife!!!! Anyway, thanks for Brandyn and her collegues for supporting us to sta

Price per night from

$325

1 / 22

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,

Price per night from

$80

1 / 15

Hale Kimo

Kailua house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$775

1 / 14

Lanikai Ohana Hale

Kailua house

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$225

1 / 17

Garden of Dreams - swimming pool on property -

Kailua studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 50 minutes

Price per night from

$87

1 / 21

“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).

Price per night from

$195

1 / 62

Orchid studio in home. Private entrance & bathroom

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$66

1 / 8

Martins Hale

Kailua cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$195

1 / 15

Ocean Breeze - Kailua Bay Oceanfront Home w/spectacularly sweeping views

Kailua house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$2,000

1 / 23
Viewing 38 of 1,567

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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