Skip to content
Some content has been automatically translated. Show original language

Kailua beach 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.

SUPERHOST
  1. Entire guesthouse
  2. Kailua
Kailua Hawaiian Studio

Welcome to our simple, beautiful Hawaiian inspired home. We are a surfing, vegetarian, family. We would like you to feel welcomed at our home for your stay here in Hawaii. We hope you have a healthy, fun, and peaceful stay here. Make this place a one stop shop! We have a car rental available for you listed on Turo. Click the link to match up your dates! Check out my car on Turo! https://turo.com/us/en/car-rental/united-states/kailua-hi/mazda/3/938218

$100 per night
  1. Private room
  2. Kailua
Relaxing Room Close to Kailua Beach

Our relaxing private room is perfect for those looking to visit our Hawaii on a budget. It accommodates 1-2 occupants and is complete with a queen size bed, central air conditioning, a mini refrigerator, microwave, coffee maker, toaster, and dishes for light cooking. This unit is centrally located in Kailua with a short 5 min walk to the famous Kailua beach and a 10 min walk into Kailua town.

$55 per night
  1. Private room
  2. Kailua
Tropical Oasis in Paradise -- The Pikake

Aloha & Welcome to Manu Mele Bed and Breakfast Manu Mele literally means Bird Song in Hawaiian. Each morning, Manu Mele Bed & Breakfast is visited by many different types of birds. These birds come and share the comforts of Manu Mele. Share this experience with us and wake up to the songs of birds. We are located just a 5 minute walk from beautiful Kailua beach. Beach equipment available per request.

$175 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Cottages
  • Bungalows

Kailua vacation rentals

SUPERHOST
  1. Entire rental unit
  2. Kailua
Charming island style Studio - D&D's B&B
$99 per night
SUPERHOST
  1. Entire guest suite
  2. Kailua
Kailua Rental for Med/Long Term ($1,200/month)
$38 per night
SUPERHOST
  1. Entire guesthouse
  2. Kailua
Koolau Loft
$105 per night
  1. Private room
  2. Kailua
Cozy Cottage Close to Kailua Beach
$75 per night
SUPERHOST
  1. Private room
  2. Kailua
Pillows in Paradise, Private studios
$170 per night
SUPERHOST
  1. Entire home
  2. Kailua
Kailua Beach Park - 1 BR Cottage
$260 per night
SUPERHOST
  1. Entire guesthouse
  2. Kailua
Kailua Palm Studio. Walk to Beach! PERMITTED
$288 per night
SUPERHOST
  1. Entire guest suite
  2. Kailua
Kailua Cottage
$118 per night
  1. Private room
  2. Kailua
Tradewind Bungalow
$132 per night
SUPERHOST
  1. Entire home
  2. Kailua
Moku studio apartment
$130 per night
  1. Entire home
  2. Kailua
Tropical Hideaway Near the Beach
$70 per night
  1. Private room
  2. Kailua
Private Room 5 Min Away From Beach
$50 per night

Kailua home rentals

SUPERHOST
  1. Private room
  2. Kailua
Kailua Beach Home
$145 per night
  1. Entire home
  2. Kailua
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
$225 per night
  1. Entire home
  2. Kailua
The Red Ginger: Large 1 Bedroom
$199 per night
SUPERHOST
  1. Private room
  2. Kailua
Blue Kailua
$117 per night
  1. Private room
  2. Kailua
Ginger studio suite. Walk to beach.
$100 per night
  1. Entire home
  2. Kailua
____Cute Plantation House in Kailua with AC!!_____
$289 per night
SUPERHOST
  1. Entire home
  2. Kailua
Kailua Home Away From Home
$160 per night
SUPERHOST
  1. Entire home
  2. Kailua
Kailua Beach Park - 2 BR Cottage
$320 per night
SUPERHOST
  1. Entire home
  2. Kailua
Beautiful! 2 blocks to Kailua Beach
$350 per night
  1. Private room
  2. Kailua
***PARADISE FOUND: The Orchid Room at Seal Cove***
$117 per night
  1. Private room
  2. Kailua
Master BR w priv BA (Olomana) optional extra room
$99 per night
  1. Entire home
  2. Kailua
Beautiful Kailua Home, Near the Beach
$275 per night

Kailua condo rentals

SUPERHOST
  1. Entire condo
  2. Waikiki
Waikiki Beach 2minutes/mini mart 1stF/WiFi/Balcony
$42 per night
  1. Entire condo
  2. Ala Moana
Ala Moana Hotel 6F
$80 per night
SUPERHOST
  1. Entire condo
  2. Waikiki
Ocean View Parking for 1 car High Floor in the Heart of Waikiki Best Sea View Kitchen/Washlet for up to 5 people
$81 per night
  1. Entire condo
  2. Kailua
Hale Manu (Birdhouse)
$175 per night
SUPERHOST
  1. Entire condo
  2. Honolulu
Colorful Condo in Makiki
$104 per night
SUPERHOST
  1. Entire condo
  2. Waikiki
ENCHANTED BAMBOO FOREST
$120 per night
SUPERHOST
  1. Private room
  2. Downtown Honolulu
Private room in a Luxury Downtown Condo
$70 per night
SUPERHOST
  1. Entire condo
  2. Waikiki
Islander's OCEAN VIEW-Legal Unit 2 blocks to beach
$111 per night
  1. Entire condo
  2. Waikiki
Partial Ocean View♪ 1 Block from Waikiki Beach
$129 per night
SUPERHOST
  1. Entire condo
  2. Waikiki
Central Waikiki, 1 block to Beach w Parking
$128 per night
SUPERHOST
  1. Entire condo
  2. Waikiki
Central Waikiki Studio with Parking & Great View
$120 per night
  1. Entire condo
  2. Waikiki
Another Stay In Paradise! Must See!
$95 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 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.