Vacation Rentals & Apartments in Kailua

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231 apartments

Nancy's Kailua Cottage Makai

Kailua cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$223

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

  • 1 bathroom
  • sleeps 2

Price per night from

$274

Nancy's Kailua Cottage Mauka

Kailua cottage

  • 1 bathroom
  • sleeps 2

Price per night from

$223

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$320

Lanikai Beach~3 living spaces w/heated pool, spa: Sleeps 14. FALL RATES

Kailua house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 7 minutes

Price per night from

$1,602

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

Kailua house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$1,070

Responds fast! avg. 2 hours 7 minutes

Price per night from

$670

“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!

Price per night from

$235

“"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!

Price per night from

$108

Perfect Beachtown Retreat

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$130

*Your Perfect Home * Charming 2BR/2BA Apartment with Full Kitchen, W/D & AC

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$242

Price per night from

$98

Cozy Beachtown Getaway

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$92

Unique Apartment in excellent location * close to Kailua beach & town

Kailua apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$129

Island Style Homebase * 2BR * 1BA * AC * Full Kitchen

Kailua apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$185

Kakela Kai, Beachfront Kailua, Centeral A/C

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$839

Makani Moana~Lanikai ~ Spectacular Ocean+Mokulua Islands Views + A/C

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$753

Lanikai Beachfront - Sunrise over the Mokulua Islands - SPECTACULAR!

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$919

Spacious 3-Bedroom, 2-Bath Apartment with Kitchen and AC

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$242

Price per night from

$142

*Affordable Island Getaway with private yard *

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$161

Price per night from

$186

Steps to the beach * upstairs Apartment with 3 bedrooms & 2 bath* AC

Kailua apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$273

Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!

Kailua house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$660

Responds fast! avg. 2 hours 7 minutes

Price per night from

$354

Entire Guest Cottage for your Enchanted Getaway

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$171

Suite By the Sea - a bright and sparkling Apartment

Kailua house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$137

Responds fast! avg. 2 hours 7 minutes

Price per night from

$4,427

Kailua Home w/Spectacular Views, Newly Renovated

Kailua house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$653

Responds fast! avg. 2 hours 7 minutes

Price per night from

$5,696

Price per night from

$155

Price per night from

$594

LAST MINUTE DEAL: Hale Mokolea in Lanikai - OPEN JULY 24th for 1 Month!

Kailua cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$192

Price per night from

$2,380

Laiki - Steps to Kailua Beach w/Heated Salt Water Pool+Spa

Kailua house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 7 minutes

Price per night from

$1,595

Omao - Kailua, Oahu - Cute Kailua Beach House - NEW RENTAL

Kailua house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$338

* Marbella Lane - Sunshine Seascape | Ocean View

Kailua house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 7 minutes

Price per night from

$172

Kailua Beachfront w/Heated Pool/Spa~ JULY CXL - SPECIAL RATE OFFERED

Kailua house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 7 minutes

Price per night from

$3,601

Viewing 38 of 231
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

SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown
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
Available 5-15-24 to 6-28-24 Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views
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
Nancy's Kailua Cottage Mauka
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!see more

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