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Vacation rentals in Kailua

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Top-rated vacation rentals in Kailua

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

Salty, Sandy Kailua Sea Shores, & So Much More
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
Salty, Sandy Kailua Sea Shores, & So Much MoreThis cozy, beachy bungalow is within a 5-10 minute walk to the world famous Kailua Beach. Listen to the sounds of the waves at night as you relax after your fun-filled beach day. The studio is bright and clean with air conditioning, a full kitchenette, comfy Queen size bed, clean bathroom and a private gated entrance. Kailua is a special community with beautiful beaches, great restaurants, boutique shopping and a relaxed atmosphere. We have the space professionally cleaned after every stay!
Holiday Palms-2 blks fr Kailua Bch/walk to town
SUPERHOST
Entire guesthouse · 4 guests · 2 beds · 1 bath
Holiday Palms-2 blks fr Kailua Bch/walk to townSecluded on the side of our Kailua home Holiday Palms is a private cottage. It is a one-bedroom unit, steps from Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio. In order to comply with Oahu's 30 night minimum short term rental laws, the suite will be blocked for 30 consecutive nights surrounding the agreed upon occupancy even if the guests occupy less than 30 nights. You are not required to stay or pay for 30 days. Please contact us if you have any questions..
Beachy luxury you'll never want to leave!
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Beachy luxury you'll never want to leave!If you're planning on visiting Kailua for thirty 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. Our minimum stay: 30 days (We are compliant with local laws so, sorry, at this time we cannot accommodate stays of fewer than 30 days.) The rate shown is our discounted 30+ day. rate.

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Other great vacation rentals in Kailua

SUPERHOST
  1. Private room
  2. Kailua
Tropical Oasis in Paradise -- The Hibiscus
$186 per night
SUPERHOST
  1. Entire cottage
  2. Kailua
Step back in time in this Plantation Cottage by the beach
$210 per night
  1. Entire residential home
  2. Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
$225 per night
SUPERHOST
  1. Entire cottage
  2. Kailua
* Tiny House * Best Location in Kailua
$121 per night
  1. Private room
  2. Kailua
Quiet, Pleasant Room in Kailua
$50 per night
SUPERHOST
  1. Entire rental unit
  2. Kailua
Private & Charming Kalama Studio
$103 per night
SUPERHOST
  1. Entire guesthouse
  2. Kailua
Kailua Palm Studio. Walk to Beach! PERMITTED
$274 per night
  1. Private room
  2. Kailua
Private Room Close to Kailua Beach
$55 per night
  1. Entire guest suite
  2. Kailua
Kailua Town studio! 30 day minimum booking
$120 per night
SUPERHOST
  1. Private room
  2. Kailua
Pillows in Paradise, Private studios
$170 per night
SUPERHOST
  1. Entire guest suite
  2. Kailua
Kailua Rental for Med/Long Term ($1,200/month)
$38 per night
SUPERHOST
  1. Private room
  2. Kailua
Papaya Paradise B&B Mauka Studio **Licensed**
$178 per night

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.


How do I get around Kailua?

Kailua is less than 30 minutes’ drive from Daniel K. Inouye International Airport (HNL) in Honolulu, the primary airport on the island of Oahu. You’ll likely want to rent a car here, and car rental desks are located on the ground floor of the terminal across from baggage claim. Rideshare services are on the second level (departures) at the airport, with signs directing visitors to three pickup locations. A bus service departs from the Main Terminal Diamond Head every 30 minutes, and takes a little over an hour to drop visitors near the entry point of Kailua’s city center.


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 visit Kailua. 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.