Skip to content

Kailua vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Kailua

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Rental unit in Kailua
Beautiful Kailua Studio Near Beach
Come enjoy the beautiful Windward side of Oahu in our newly renovated private guest suite with own separate entrance. Fully furnished kitchen, bath and spacious room to enjoy your Hawaiian vacation. Very close to world-famous Kailua and Lanikai beach. In order to comply with the new Oahu short term rental regulations, our studio is available for a minimum of 30 days (regardless of actual occupancy dates). Keep that in mind as our 30-day rate (+amenities) may be less than a Waikiki hotel room.
$150 per night
SUPERHOST
Rental unit in Kailua
Beachy luxury you'll never want to leave!
If you're planning on visiting Kailua for 30 days or longer, you will fall in love with our gorgeous apartment overlooking Kailua Beach. Simply the prettiest apartment, in the most beautiful quiet neighborhood in amazing laid-back Kailua. Please note the following from the City and County of Honolulu: “This property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.”
$150 per night
SUPERHOST
Guest suite in Kailua
Quiet, Comfortable Home in Beautiful Kailua, HI
Welcome to your peaceful and safe home-away-from-home in beautiful Kailua, Hawaii! (Approximately 2.5 miles from world-famous Kailua Beach.) **Please note: The City & County of Honolulu has passed a bill that requires a 30-day minimum for all short-term rentals. Our pricing reflects that 30-day minimum requirement. Mahalo!**
$100 per night

Stay near Kailua's top sights

Photo of Kailua Beach Park
Kailua Beach Park200 locals recommend
Photo of Kailua Beach Adventures
Kailua Beach Adventures40 locals recommend
Photo of Whole Foods Market
Whole Foods Market370 locals recommend
Photo of Pillbox Hike
Pillbox Hike178 locals recommend
Photo of Buzz's Steakhouse
Buzz's Steakhouse136 locals recommend
Photo of Boots & Kimo's Homestyle Kitchen
Boots & Kimo's Homestyle Kitchen52 locals recommend

Kailua beach vacation rentals

Guest suite in Kailua
Stunning Views. To inquire please contact owners.
$107 per night
SUPERHOST
Rental unit in Kailua
Charming island style Studio just steps to Kailua
$99 per night
SUPERHOST
Guest suite in Kailua
🌺Adorable 1 bedroom place, walk to the beach
$155 per night
SUPERHOST
Guest suite in Kailua
Kailua Cottage
$118 per night
SUPERHOST
Rental unit in Kailua
Secluded Kailua Beach Bungalow with Private Garden
$229 per night
Guesthouse in Kailua
Koolau Loft
$105 per night
SUPERHOST
Private room in Kailua
Lanikai Ocean View Studio
$125 per night
SUPERHOST
Guesthouse in Kailua
Lanikai Ocean View Retreat with saltwater pool
$150 per night
Guest suite in Kailua
Kailua Hale Kipa Home away from Home! 30 day min.
$115 per night
SUPERHOST
Cottage in Kailua
Kailua Beach footsteps away
$185 per night
SUPERHOST
Guesthouse in Kailua
Karibu Cottage in Beautiful Lanikai
$129 per night
SUPERHOST
Rental unit in Kailua
Central 1 bd apt 30day min - Pet friendly
$157 per night
SUPERHOST

Kailua house rentals

Home in Kailua
Kailua Beach Park - 1 BR Cottage
$285 per night
Home in Kailua
Steps to quiet part of Kailua Beach, AC, New Reno
$209 per night
SUPERHOST
Private room in Kailua
BoHo Beach Resort Living! W/Pool
$160 per night
SUPERHOST
Home in Kailua
The Red Ginger: Large 1 Bedroom
$199 per night
SUPERHOST
Home in Kailua
Kailua Beach Park - 2 BR Cottage
$345 per night
Home in Kailua
Kailua, home, yard, BBQ, 7 min drv to beach/town
$170 per night
Home in Kailua
Tropical Hideaway Near the Beach
$70 per night
SUPERHOST
Private room in Kailua
Quiet comfortable room for your longer stay
$60 per night
Home in Kailua
Kailua Home Away From Home
$175 per night
SUPERHOST
Home in Kailua
Waterfront Lanikai Beach Compound
$349 per night
Home in Kailua
Tropical Cottage w/Pool, Lanai & AC, Walk to Beach
$236 per night
SUPERHOST
Private room in Kailua
Tradewind Bungalow
$150 per night
SUPERHOST

Kailua condo rentals

Condo in Kailua
Hale Manu (Birdhouse)
$175 per night
Condo in Waikiki
Modern Waikiki Studio With Gorgeous Views
$136 per night
Condo in Waikiki
Stylish Studio Waikiki Incredible Views 30th Floor
$101 per night
Condo in Waikiki
Newly Renovated Cozy Home
$118 per night
SUPERHOST
Condo in Waikiki
Central Waikiki, 1 block to Beach w Parking
$134 per night
SUPERHOST
Condo in Waikiki
Waikiki Studio in perfect location
$115 per night
Condo in Waikiki
Islander's Hideaway - 2 Blocks to beach!
$116 per night
Condo in Waikiki
Spectacular Oceanview Studio, Beach, Free Parking
$166 per night
SUPERHOST
Condo in Waikiki
Newly decorated,Central Waikiki,Ocean view W wifi
$113 per night
SUPERHOST
Condo in Waikiki
Pineapple Dreams: 2 Blocks to Famous Waikiki Beach
$114 per night
Condo in Waikiki
High Speed Internet, no Airbnb Service Fee !
$108 per night
Condo in Waikiki
Free Assigned Parking, Close to Beach, AC, Kitchen
$162 per night
SUPERHOST

Your guide to Kailua

Welcome to Kailua

With stretches of powdery white sand beaches, two reef-protected lagoons, and temperatures kept on the comfortable side of cool by ever-present trade winds, it’s no surprise Kailua is no longer the secret destination guarded by seasoned island vacationers that it once was. Located on the windward side of Oahu on a peninsula overlooking the crescent-shaped Kailua Bay and the Koolau Mountain range, Kailua is beloved for its small beach town vibe — a mellow yin to Honolulu’s metropolitan yang, with only a 25-minute drive separating the destinations.

There’s also an increasing possibility of rubbing well-tanned shoulders with vacationing celebrities drawn to the same soft sand beaches and tranquil aquamarine waters delivering on the promise of paradise. In Kailua you can revel in a variety of water sports. Hikers have a range of challenging trails to choose from, some leading to breathtaking mountaintop views, others to such secluded mountain-fed pools as Maunawili Falls, along with a network of leisurely footpaths awaiting within the 830 acres of Kawainui Marsh.


When is the best time to stay in a vacation rental in Kailua?

With an average temperature of 81 degrees Fahrenheit, there’s really no bad time to stay in one of Kailua’s vacation rentals. Months spanning from spring through fall generally offer the best balance between agreeable (dry) days, with sparser crowds that spike after Thanksgiving. Kailua’s windward location on the island means sweltering heat will rarely be a concern here, and the weather is almost always pleasant. Mornings can be a little muggy, though, before the trade winds flush out the humidity, perpetually moving clouds overhead to reveal the shockingly blue skies. If you plan to travel from November through early spring, come prepared for rainfall, including footwear outfitted for muddy conditions.


What are the top things to do in Kailua?

Lanikai Beach

Lanikai Beach is often described as one of the world’s greatest beaches, and it’s easy to see why, with its breathtaking stretches of sand and ocean overlooking two nearby islets, the Na Mokulua. The waters here are typically calm, with a protected coastline buffered from windpowered waves thanks to a sizable reef offshore, making it one of the more swimmable spots on Oahu. These placid coastal waters are hard to beat — especially for kayaking and paddleboarding — tempting the more adventurous to paddle around those two offshore islands colloquially referred to as the Mokes.

Kawainui Marsh

Binoculars and a camera are a must while visiting Kawainui Marsh, the state’s largest protected wetlands, a sanctuary where many of Oʻahu’s endemic, endangered, and migratory birds, fish, and other aquatic life can be observed in their natural habitat. Travel by foot or by bike along a paved three-mile round path in a watershed that fed ancient Hawaiians with its abundance.

BookEnds

If you identify as a bibliophile and/or a lover of Hawaiian history, you might lose yourself once entering the door of this small neighborhood bookstore. BookEnds is filled with an extensive collection of Hawaiiana reflecting the islands’ history through photography, arts and crafts, architecture, and music.

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Kailua