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Vacation Rentals & Apartments in Kailua

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611 apartments

Nancy's Kailua Cottage Makai

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 53 minutes

Price per night from

$96

Plantation Charm in Kailua

Kailua bungalow

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$209

Sheffield Studio Walk to Kailua Beach or Town

Kailua b&b

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 48 minutes

Price per night from

$276

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. 3 hours 53 minutes

Price per night from

$96

Sheffield Suite Walk to Kailua Beach or Town

Kailua b&b

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 48 minutes

Price per night from

$276

Steps to Lanikai Beach~3 living spaces w/pool

Kailua house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$833

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

Kailua house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$466

Great Location - Very Clean - 1 Bedroom

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$171

Mokulua Aina~Lanikai Steps to Lanikai Beach. SPECIAL FALL RATES!

Kailua house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$321

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

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. 1 hour 45 minutes

Price per night from

$226

“"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

$114

Steps to Kailua Beach * LAST MINUTE OPENING * 2 bedrooms & 1 1/2 bath * AC

Kailua house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$300

Perfect Beachtown Retreat

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 40 minutes

Price per night from

$121

Air conditioned Hi'ilani Hideaway with full kitchen - sleeps up to 4 adults

Kailua apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$158

* Tiny House * Best Location in Kailua

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$97

Price per night from

$121

Private & Charming * Kalama Studio

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$91

Cozy Beachtown Getaway

Kailua apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$103

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

Kailua apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$150

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

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$89

Island style Homebase * 2 bedroom & 1 bath - Central Air

Kailua apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$184

Garden of Dreams - swimming pool on property

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$108

* LAST MINUTE OPENING * Tropical Garden Cottage

Kailua cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$118

Lovely Pool Studio with private entrance & bath

Kailua house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$100

Kakela Kai, Beachfront Kailua, Centeral A/C

Kailua house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,114

Your Private Place in Paradise - Sleeps 2 to 4!

Kailua apartment

1 bedroom / 1 bathroom / sleeps 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!

Price per night from

$171

Lanikai Beach Front - Sunrise over the "Mokes"

Kailua house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$600

***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared)

Kailua private room

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$130

Gorgeous 5BR Kailua Beachside Home - Sleeps 12

Kailua house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 5 minutes

Price per night from

$1,067

Kailua, Entire 3 Bedroom Home, carport, yard, BBQ

Kailua house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 32 minutes

Price per night from

$172

Tropical Kailua Studio on the Water w/Private Pool

Kailua studio

Studio / 1 bathroom / sleeps 2

Price per night from

$172

Kailua, Cozy, 2 bedroom, duplex home, carport, yard, BBQ

Kailua house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 32 minutes

Price per night from

$126

Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of

Kailua house

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 15 minutes

Price per night from

$2,415

Kailua, Cozy, Spacious Duplex Home, carport, yard, BBQ

Kailua house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 32 minutes

Price per night from

$138

Sunset Studio

Kailua apartment

1 bedroom / 1 bathroom / sleeps 1

Price per night from

$97

Large Lanikai Ocean Front w/Pool

Kailua house

6 bedrooms / 6 bathrooms / sleeps 18

Price per night from

$1,067

White Sands Escape by the Beach

Kailua house

1 bedroom / 1 bathroom / sleeps 1

Price per night from

$74

Cozy Cottage 5 Minute Walk to Kailua Beach

Kailua house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$81

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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

Tropical Kailua Studio on the Water w/Private Pool
Very nice.

Great place away from all the big resort hotels. Feels like we are living like the locals. Very comfortable accommodations. Fridge and microwave but no kitchen. Kailua and the windward have great beaches, great local eateries and wonderful people. Our host are available to us but invisible as well. They have done an excellent job of stocking everything you might need for your trip- beach towels and chairs, kayaks, snorkeling gear, coolers...! Overall, a great week! KBsee more
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 – 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
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
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
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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