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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua vacation rentals
Kailua beach vacation rentals
Kailua home rentals
Beach home rentals in Kailua
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.
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.
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.
Destinations to explore
- Cottage rentalsKailua
- Waterfront rentalsKailua
- Family-friendly rentalsKailua
- Rentals with poolsKailua
- Beachfront rentalsKailua
- Condo rentalsKailua
- Rentals with a washer and dryerKailua
- Rentals with a hot tubKailua
- Beach house rentalsKailua
- House rentalsKailua
- Bungalow rentalsKailua
- Fitness-friendly rentalsKailua
- Rentals with a kayakKailua
- Rentals with beach accessKailua
- Rentals with outdoor seatingKailua
- Pet-friendly rentalsKailua
- Apartment rentalsKailua
- Monthly RentalsKailua
- Guesthouse rentalsKailua
- Private suite rentalsKailua
- Kid-friendly rentalsKailua
- Rentals with a patioKailua
- Yurt RentalsUnited States
- Yurt RentalsUnited Kingdom
- Castle RentalsUnited States
- HouseboatsUnited States
- Holiday CaravansUnited Kingdom
- Private Island RentalsUnited States
- Farm HousesUnited States
- Farm CottagesUnited Kingdom
- Cabin RentalsAustralia
- Luxury CabinsUnited Kingdom
- Luxury CabinsUnited States
- Holiday ChaletsUnited Kingdom
- Cottage RentalsUnited States
- Holiday CottagesUnited Kingdom
- Mansion RentalsUnited States
- Villa RentalsUnited Kingdom
- Holiday BungalowsUnited Kingdom
- Bungalow RentalsUnited States
- Condo RentalsUnited States
- Holiday ApartmentsAustralia
- Holiday HousesUnited States
- Holiday HousesUnited Kingdom
- Private Holiday RentalsUnited Kingdom
- Big House RentalsUnited States
- Big CottagesAustralia
- Large VillasUnited Kingdom
- House Rentals with a PoolUnited States
- Cabin Rentals with a PoolUnited States
- Villas with a PoolUnited Kingdom
- Apartments with a Hot TubUnited States
- Holiday Cottages with a Hot TubUnited Kingdom
- Beach CabinsUnited States
- Beach CondosUnited States
- Beachfront RentalsUnited States
- Beach HousesUnited Kingdom
- Beach VillasUnited Kingdom
- Coastal CottagesUnited Kingdom
- Pet-Friendly Vacation RentalsUnited States
- Pet-Friendly Beach RentalsUnited States
- Pet-Friendly Cabin RentalsUnited States
- Dog-Friendly CottagesUnited Kingdom
- Luxury Dog-Friendly CottagesUnited Kingdom