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Vacation Rentals & Apartments in Kailua

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781 apartments

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 41 minutes

Price per night from

$96

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$462

Kailua Beach Wagon

Kailua camper van

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$133

Lovely 2 Bedrooms Homeaway in Kailua Beach Town

Kailua house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$206

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

/ 1 bathroom / sleeps 2

Price per night from

$167

Beachfront Kailua, Oahu

Kailua house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$520

Palione Papalani~Steps from Kailua Beach~large, remodeled with pool&spa

Kailua house

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,500

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!

Responds fast! avg. 41 minutes

Price per night from

$96

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$196

Luxury home(s) just steps away from Kailua Beach

Kailua house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,273

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

$2,571

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

Kailua house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$2,571

Oahu Apartment w/ Patio - Steps to Kailua Beach!

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 5 minutes

Price per night from

$144

Kailua Suite

Kailua studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 14 minutes

Price per night from

$176

Great Location - Very Clean - 1 Bedroom

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$174

Kehaulani - Lanikai~ Stunning Ocean Views~ private residence

Kailua house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,786

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. 1 hour 28 minutes

Price per night from

$162

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

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,786

Tradewind Bungalow, in Kailua on Oahu

Kailua house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$239

E Komo Mai Private Bedroom near Kailua Beach Town

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$156

Walker's Lanikai Beach House~Oceanfront restored Historic home

Kailua house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$1,500

Kailua Beach Aloha Cottage

Kailua cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$196

Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua All Taxes Included

Kailua apartment

1 bedroom / 1 bathroom / sleeps 4

“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). If you rent from Patty you will be very happy you made the decision. 1) Hosts - Patty was so welcoming, friendly and helpful without ever being intrusive. She was a wealth of knowledge and was so willing to share her insights to ensure we hit the best spots at the right times to ensure a great experience. 2) Apartment - The pictures are very accurate so you really get what you see. The apartment has very "homey" feeling. The decor is local and tasteful, the kitchen fully equipped. The Lanai had really nice breezes and sunrises. It also had hooks which came in handy when drying things. While we didn't watch much TV there were plenty of options (cable, netflix, pandora) as well as a small stereo system. There were games to play, books to read (including several on Hawaii that we loved), and the all-important washer/dryer. 3) The Stuff - One of the things we loved about the apartment was the plethora recreational toys at our disposal. Beach chairs, umbrellas, boogie boards, snorkels, masks, coolers, sup's, Kayaks, bikes, etc. If you needed it, they had it which was huge for a family that spent everyday on the ridiculously nice beaches a short drive away. 4) The Location - Check it out on the map. It sits just above town in a neighborhood. It is not walking distance from the beach or town but a 5 minute drive (and free street parking) gets you there before you know it. It is walking distance to a great yoga co-op (Aloha Yoga Kula) which we went to several times and loved. Some may want to be closer to the action but we found the location close enough. All in all, this is a fantastic rental and we thought a great value. The personal touch offered by Patty puts it over the top. Do yourself a favor and book it before someone else does!

Responds fast! avg. 2 hours 40 minutes

Price per night from

$226

Comfortable house right on sandy part of Lanikai

Kailua house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$405

Responds fast! avg. 3 hours 24 minutes

Price per night from

$258

Ke'aloha

Kailua apartment

4 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$587

Unforgettable Beachfront Oasis

Kailua villa

6 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,852

Lanikai Breeze

Kailua house

5 bedrooms / 5 bathrooms / sleeps 12

Price per night from

$1,516

Lanikai Cottage

Kailua apartment

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$657

Perfect Beachtown Retreat

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$122

D+D's Cottage - Best Location in Kailua

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$60

Kailua Beach Studio - Tiki Room

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$76

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

$4,043

Air Conditioned Charming Kalama Room

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$53

Inquire for Discounts! Beachfront Hawaiian Cottage

Kailua house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 32 minutes

Price per night from

$456

Kailani Villa

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,516

Kailua Beach House

Kailua house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,261

Kailua Beach Studio - Coral Room

Kailua studio

Studio / 1 bathroom / sleeps 4

Price per night from

$89

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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
Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua All Taxes Included
Hostess with the Mostest!

We just returned from a wonderful, relaxing 12-stay at Kauhale. The apartment had everything we could have possibly needed during our stay, including beach towels, boogie boards, bikes, kayaks, insulated grocery bags, coolers, snorkel gear, etc. Patty and Bob have clearly put tremendous thought and effort into making it such a special place, with every amenity one could imagine. We loved the Hawaiian decor, the lovely bedding, the plush towels, and the fully-equipped kitchen. The deck off the apartment is to die for. The ceiling fans and trade winds kept the apartment cool and comfortable even though it was a warm time of year. Beautiful fresh flower arrangements greeted us upon our arrival along with a delightful gift basket of coffee, fruit, macadamia nuts, Maui potato chips, and more. Patty is a delightful hostess--warm, attentive, and always helpful but never intrusive. We highly recommend this rental and would stay there again in a heartbeat!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
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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