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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.

Kailua Beach Park - 1 BR Cottage
SUPERHOST
Entire residential home · 4 guests · 2 beds · 1 bath

Kailua Beach Park - 1 BR CottageKailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a fully legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm."

Tranquil Tropical Beach Hideaway
SUPERHOST
Entire guest suite · 3 guests · 2 beds · 1 bath

Tranquil Tropical Beach HideawayCome enjoy this private Hawaiian style guest suite in a tranquil setting of tropical flowers and palms. Sip coffee or wine while you and listen to the birds sing at your outdoor bistro. Take a dip and catch some rays in the blue-tiled pool. Rinse the sand from your toes after a stroll or surfing at Kailua's Castles beach, a short 8 minute walk from your door to sand. Available for a single rental period per 30d interval to comply with O’ahu rental laws.

Kolea Landing Modern Beach House w/ Double Master
SUPERHOST
Entire guest suite · 4 guests · 3 beds · 2 baths

Kolea Landing Modern Beach House w/ Double MasterAloha and Welcome to Kolea Landing A short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 1,600 sf guest suite is the perfect blend of island and modern living. Complete with two master bedrooms each with an en suite bathroom, a full size kitchen, dining room, living room, laundry room, and outdoor lanai. Our property also includes 2 off street parking, which is coveted if you have ever been to Lanikai. Prime location and tons of amenities!

Vacation rentals for every style

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Popular amenities for Kailua vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Kailua

  1. Entire guest suite
  2. Kailua
DaLight - A beautiful home in a quiet neighborhood
$129 per night
  1. Entire guest suite
  2. Kailua
Absolutely Oceanfront Views-60' Waterfall Lap Pool
$343 per night
  1. Entire guest suite
  2. Kailua
Dolphin Suite - Wonderful Location!
$95 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 residential home
  2. Kailua
Kailua Beach Park - 2 BR Cottage
$280 per night
SUPERHOST
  1. Private room
  2. Kailua
Pillows in Paradise, Private studios
$170 per night
SUPERHOST
  1. Entire residential home
  2. Kailua
Tropical Oasis in Kailua-30 day minimum
$355 per night
SUPERHOST
  1. Private room
  2. Kailua
Blue Kailua
$91 per night
  1. Entire rental unit
  2. Kailua
Norfolk private retreat entire guest suite w/pool
$325 per night
  1. Private room
  2. Kailua
***PARADISE FOUND: The Orchid Room at Seal Cove***
$114 per night
SUPERHOST
  1. Entire guesthouse
  2. Kailua
Holiday Palms-2 blks fr Kailua Bch/walk to town
$159 per night
SUPERHOST
  1. Entire guest suite
  2. Kailua
Kailua Pineapple Studio. Walk to Beach! PERMITTED
$245 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.

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