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Vacation Rentals & Apartments in Kailua

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655 apartments

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$95

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$207

Kailua Beach Wagon

Kailua camper van

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$149

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

/ 1 bathroom / sleeps 2

Price per night from

$166

Palione Papalani~Steps from Kailua Beach w/ private pool & hot tub

Kailua house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,800

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, great bed, nicely appointed full kitchen, available barbeque and bicycles, some picnic supplies, you name it! There is a nice lanai out from which to relax, read, or just stare off to the distant mountains. Rick, one of the owners, is very friendly and extremely knowledgeable about Oahu and the other islands. He directed us to a tide pool area (Better be in some kind of shape!), a local hiking trail (ditto), and had all sorts of information available. The cottage is a short walk from a beautiful beach (almost a cliché in Hawaii), and a very short drive to the town's commercial area, which has several grocery stores and a selection of reasonably priced restaurants if you're tired of cooking. All in all, a great place to stay and relax!

Price per night from

$95

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Hale Mokulua ~ with private pool & spa~steps to Lanikai Beach~3 living spaces

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$3,571

Kailua Beachfront~private~newly renovated home w/stunning views

Kailua house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,929

Kailua Suite

Kailua studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 8 minutes

Price per night from

$173

Great Location - Very Clean - 1 Bedroom

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$194

Kehaulani - Lanikai~ Stunning Ocean Views~ private residence

Kailua house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,500

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 as it floated through the windows every morning. Lovely! Sabine thought of everything to make our stay comfortable. We were welcomed with fresh fruit and a Beautiful arrangement of fresh Hawaiian flowers. There were beach items available for us to use including a beach umbrella, chairs, mats and beach bag. The location was ideal. We could easily walk to Kailua Beach or to Kailua town. Kailua town has plenty of upscale shops and restaurants. There was even a brand new Target there. We would definitely stay there again. It was lovely!

Responds fast! avg. 3 hours 18 minutes

Price per night from

$114

Mokulua Aina~Lanikai tropical retreat with pool ~ steps to Lanikai Beach

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,500

Walker's Lanikai Beach House~Oceanfront *APRIL CANCELLATION - CALL NOW*!

Kailua house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$1,800

Steps from Lanikai Beach! Private Laidback Luxury Home w/Pool, Lanikai Breeze

Kailua house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,517

3bd/2ba Beachy Charm Home w/Private Pool & Close Walk to beach. Lanikai Cottage

Kailua apartment

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$573

Perfect Beachtown Retreat

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 50 minutes

Price per night from

$119

D+D's Cottage - Best Location in Kailua

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$91

Kailua Beach Studio - Tiki Room

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$133

Large Private Luxury Home w/Pool, A/C and Ocean Views. Kailua Shores Estate

Kailua apartment

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$4,042

Charming Kalama Studio with AC

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$94

Kailani Villa - Holiday Availability! Inquire for possible discounts!

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,608

Kailua Beach House

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,271

Kailua Beach Studio - Coral Room

Kailua studio

Studio / 1 bathroom / sleeps 4

Price per night from

$150

Island Retreat 2 blocks from Kailua Beach Park and Downtown

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$139

Lanikai Ohana Hale

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$228

Bright Kailua House w/Pool & Patio by Beaches

Kailua house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 14 minutes

Price per night from

$196

Last minute opening *Garden Studio with pool on property*

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$101

Sunny Apartment in excellent location - short walk to Kailua beach & town

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$139

Price per night from

$2,081

Ocean view, Villa, Mokulua Island view, Pool, Luxury, Lanikai Ocean View Villa

Kailua house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$2,022

Cozy Beachtown Getaway

Kailua apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 7 minutes

Price per night from

$101

Kapaka Cottage with 2 bedroom & 1 bath - Central Air & full kitchen

Kailua apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$171

Tropical Garden Cottage

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$118

Kailua Shores Estate 8 Bedroom

Kailua house

8 bedrooms / 9 bathrooms / sleeps 16

Price per night from

$6,568

Beach House w/amazing ocean views & 10 steps from beach access. Hale Kalio

Kailua house

6 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$1,004

D&D's B&B- sweet island style Studio

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$83

Viewing 38 of 655
rentals in Kailua

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About Kailua

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.

Top Destination reviews

Kailua, Cozy, 2 bedroom, duplex home, carport, yard, BBQ
Truly A Fantastic Place

Wow what a fantastic place!!! I travel a lot and am a picky person but must say this place is fabulous. First, the location is perfect - nice residential neighborhood inside beautiful Kailua yet not to far from the H3 or Pali exits that take you to the other side of the island. Really short drive to Kailua Town and popular local beaches. Second, this duplex home with a wrap around yard which is well landscaped offers a wonderful play area for me and my grand child. Covered parking inside the carport is a definite plus. Third, beautifully furnished and decorated furniture and furnishings allowed me to relax and enjoy my stay. A power whole house fan, along with ceiling fans in every room and ac units in the bedroom allowed for great ventilation. Fourth, the home is stocked with many amenities I did not have to purchase such as: laundry and dish washing detergents, shampoo, conditioners, local coffees, beach and bath towels, mats, boogie boards, umbrellas etc etc Fifth, and most importance was the kindness and caring from these wonderful hosts. Now I understand why they are rated Super Host - because I had a Super stay! I plan to return here again to visit my grand child!!! Sincerely, Ninasee more
SUITE ALOHA – Remodeled, Romantic Island Retreat
Beautiful accommodation. Laid back feel.

Our accommodations were beautiful, clean and exactly what we were looking for. The location is fantastic and we were only a few minutes from Kailua and Lanikai beaches, as well as a very short walk to downtown Kailua. Sabine and Ray are excellent hosts. Upon our arrival, we had time to settle in and relax; we even found a small fruit plate to welcome us. Later, Sabine stopped by to greet us, answer any questions we may have had, and offered recommendations on restaurants and activities in the area; Sabine even made certain to give us directions to nearby locations. This was our first trip to Hawaii, and we had a great trip. We look forward to staying here again.see more
Kailua, Cozy, Spacious Duplex Home, carport, yard, BBQ
Wonderful stay, cozy, and prime location!

This is my second time staying at this property. And, both times, it has been a great experience. It allows for great family time with my grandchildren and the convenience to be so close to the Kailua and Lanikai beaches and nearby town and all the shopping. The property is very spacious, there is a nice patio, and the community is very quiet. I have enjoyed staying at this place and I would love to go back.see more
Your Private Place in Paradise - Sleeps 2 to 4!
Loved Kailua!

We had a wonderful time staying with Carol and family. They were very virtuous and had plenty of everyday items you need while staying in their home. We loved the quick walk to Muddy Waters Coffee and the beach! It was a great experience and would recommend their home anytime. Thank you Carol and John!see more
4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach
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 stay. There are small playground in 30 m from the house. Our kids went there every morning. … see more
Plantation Charm in Kailua
Accommodating!!

The owners were a lifesaver. We were stranded in Hawaii with our family of 6 celebrating our daughter's college graduation and the rental I booked online was a scam!!! We needed accommodations ASAP and the owners moved their schedules around to meet our needs within 12 hours … see more

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