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.

Superhost
Home in Kailua
Kailua Beach Park - 1 BR Cottage
Kailua 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 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." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!
Jun. 5 – 12
$433 CAD per night
4.85 out of 5 average rating, 340 reviews
Guest favourite
Home in Haleiwa
Oceanfront Oahu North Shore Hawaii Private 3b Home
Discover island paradise and the best view on Oahu’s North Shore! Nestled on the shore of legendary Waimea Bay Point, this home is the gateway to an authentic Hawaiian experience. Lounge on the covered lanai feet from lapping surf watching whales, dolphins, turtles, surfers, and incredible sunsets. Extremely clean with all the necessities. Steps to 3 sandy beaches Waimea Bay, Shark’s Cove,and Three Tables. This is the perfect family getaway, allowing you to live the true North Shore lifestyle.
Jan. 24 – 31
$1,861 CAD per night
4.96 out of 5 average rating, 161 reviews
Guest favourite
Condo in Kahuku
SEArider TWO at Turtle Bay (1 bedroom / 1 bath)
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)
Feb. 2 – 9
$674 CAD per night
4.91 out of 5 average rating, 146 reviews

Popular amenities for Kailua vacation rentals

Stay near Kailua's top sights

Kailua Beach Park200 locals recommend
Whole Foods Market370 locals recommend
Pillbox Hike178 locals recommend
Boots & Kimo's Homestyle Kitchen51 locals recommend
Kailua Beach Adventures40 locals recommend
Buzz's Steakhouse136 locals recommend

Other great vacation rentals in Kailua

Superhost
Condo in Honolulu
The Best View Studio in Waikiki
Nov. 27 – Dec. 4
$281 CAD per night
4.93 out of 5 average rating, 165 reviews
Guest favourite
Condo in Kahuku
The Coloradoan
Nov. 28 – Dec. 5
$293 CAD per night
4.86 out of 5 average rating, 110 reviews
Guest favourite
Condo in Honolulu
Waikiki Beachfront, Amazing Views, Amazing Pools
Dec. 11 – 18
$1,080 CAD per night
4.95 out of 5 average rating, 215 reviews
Superhost
Guesthouse in Kailua
The Banyan Beach Bungalow
May 25 – Jun. 1
$946 CAD per night
5.0 out of 5 average rating, 5 reviews
Guest favourite
Cottage in Kailua
Kailua Ohana Cottage close to beach
Jan. 31 – Feb. 7
$553 CAD per night
4.91 out of 5 average rating, 35 reviews
Guest favourite
Villa in Kailua
Honu Suite at La Bella’s-Walk to Beach-Licensed
Apr. 6 – 13
$809 CAD per night
4.98 out of 5 average rating, 60 reviews
Guest favourite
Guesthouse in Kailua
Kailua Surf Shack: Your Hawaiian Adventure!
Aug. 22 – 29
$496 CAD per night
4.95 out of 5 average rating, 57 reviews
Guest favourite
Home in Kailua
Cute & Charming, Minutes to Town and Kailua Beach
Jan. 29 – Feb. 5
$848 CAD per night
5.0 out of 5 average rating, 34 reviews
Superhost
Home in Kailua
Tropical Cottage w/Pool, Lanai & AC, Walk to Beach
Feb. 19 – 26
$1,484 CAD per night
4.88 out of 5 average rating, 49 reviews
Superhost
Apartment in Honolulu
Breathtaking: Balcony Bliss at Wayfinder Waikiki
Aug. 21 – 28
$271 CAD per night
4.78 out of 5 average rating, 628 reviews
Guest favourite
Treehouse in Honolulu
Secluded Mahina Treehouse
Oct. 24 – 31
$1,148 CAD per night
4.95 out of 5 average rating, 65 reviews
Guest favourite
Home in Haleiwa
Haleiwa Waterfront House
Jan. 19 – 26
$1,636 CAD per night
5.0 out of 5 average rating, 34 reviews

Quick stats about vacation rentals in Kailua

Total rentals

400 properties

Rentals with dedicated workspaces

180 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

13K reviews

Destinations to explore

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