Kailua vacation rentals

Wed 1/5
Thu 2/5

Search hundreds of travel sites at once for car rental deals in Kailua

...and more

Let KAYAK do the searching

Save on your next stay

Search and compare hundreds of travel sites at once for vacation rentals in Kailua, Hawaii

We’re completely free to use – no hidden charges or fees

Best Kailua vacation rentals

Most recommended vacation rentals in Kailua

Show all
Modern Luxury Beach House Kailua
8.9 Very good
C$ 1,000+
C$ 1,000+
Parking
Free Wi-Fi

Good to know

Low season

August

High season

April

Average price (weeknight)

C$ 414

Average price (weekend night)

C$ 171
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 55% rise in price.
Average Sun. - Thu. price over the last 2 weeks.
Average Fri. & Sat. price over the last 2 weeks.

When to book a vacation rental in Kailua

Price per night / rental. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Kailua vacation rental deals

  • Kailua Beach Park Cottage - 2br is one of the most affordable Kailua vacation rentals located next to Kailua Beach Park. It is a suitable option for a small family of five. Shops and restaurants are a 5-7 min drive away while a walk to the ocean should take only about 2 min.
  • For breathtaking views of Mokulua Twin Islands and Kailua Bay, a stay in Private Beachfront Rental is recommended. The property has a private entrance. You’ll appreciate the sandy beach right outside, where you can participate in water adventures, including scuba diving and kayaking.
  • Visitors who want to stay away from the busy city life usually look for house rentals within walking distance of Kalama Beach Park. The Brand New Kailua Beach sits in a quiet location. If you want to take nature trips, the Maunawili Trailhead is only 4.3 miles from this home.
  • Unwind at Your Private Place in Paradise with spectacular views of the Koolau mountains. The apartment offers convertible beds and is situated in an upscale residential locality. Getting to Kaneohe Bay is only a few minutes by car.
  • Enjoy the convenience of staying near a shopping center by reserving one of the Kailua vacation rentals in Coconut Grove. Cute Ohana unit in Kailua Bungalow Near the Beach is conveniently located next to a walking trail leading to Kawainui Park.  For a day at the beach, take a 15 min drive to Waimanalo Beach.
  • If you came to Kailua to try paddling, stay close to the calm beginner-friendly paddling waterway Kaelepulu stream. Book your vacation at Minutes From World Famous Lanikai/Kailua Beach. Guests who come here enjoy boating and bird watching along the stream.
  • The Best Paradise- Kailua Home On Waterway is a perfect vacation home for music lovers. Stereo systems are installed indoors and outdoors. Pets are welcome if notified in advance.
  • The best vacation rental properties in Kailua are Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12 (10.0, 21 reviews), Steps to Kailua Beach-Heated Pool-Air Conditoned-7 Night Minimum Stay (10.0, 25), and Private Beachfront Rental (9.9, 64), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Kailua, you should consider visiting during the low season. The cheapest vacation homes in Kailua can be found in October and February.
  • The cheapest night for renting a vacation home in Kailua is Thursday. In contrast, the most expensive is Tuesday.
  • Book your Kailua vacation rental more than 90 days before your stay begins to get the best price.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Kailua for 8 days.

FAQs when booking a vacation home in Kailua

  • How much is a vacation rental for a week in Kailua?

    The average price for a weekly Kailua vacation rental found by KAYAK users in the last 2 weeks is C$ 6,390.

  • How much is a vacation rental for a month in Kailua?

    The average price for a monthly Kailua vacation rental found by KAYAK users in the last 2 weeks is C$ 27,388.

  • What types of vacation rentals are available in Kailua?

    There are loads of different property types that you can make your vacation home in Kailua. You’ll find houses, apartments and condos.

  • What are some of the most-loved vacation rentals available in Kailua?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Aston Waikiki Sunset.

  • Are there any pet-friendly vacation rentals in Kailua?

    There are a number of dog and pet-friendly Kailua vacation rentals, with around 4% allowing you to bring your pet along with you.

  • How much is a vacation rental in Kailua?

    KAYAK users have found vacation rentals in Kailua for as cheap as C$ 565 in the last 3 days. The average price is C$ 913.

  • How can I find vacation rentals near me in Kailua?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

  • Where should watersport enthusiasts lodge in Kailua?

    For surfing, parasailing, water-skiing, and snorkeling, rent a beachfront vacation home at Pilipu Place. If you lodge in 5 Luxury Historic Plantation Estate With Huge Yard, these and many other water sports are within easy reach.

  • Which vacation house provides easy access to car rental services in Kailua?

    If your travel itinerary includes road trips, check out Kailua house rentals with car rental services nearby. A smart choice would be Unique Find Suite in Lanikai, about 0.25 miles from Kailua Beach where you can walk comfortably on foot (8 min).

  • Which vacation rentals are suitable for solo travelers or couples in Kailua?

    Some Kailua vacation rentals are set in a laid-back neighborhood in the western corner of Auwilana Road. One of them is the Nice Studio, which is within a private home. For all your shopping needs, head to the Times Supermarket Kailua, which should take about 3 min by car.

  • Where can I stay for the best outdoor adventures in Kailua?

    Great outdoors with biking trails can be enjoyed around Lanikai Beach. Vacationers love Modern Luxury Beach House Kailua for sightseeing. It is a short walk to Kailua Beach and even closer to Lanikai Beach. Coffee lovers can head to a nearby café, about 0.6 miles from the vacation house.

Where to stay in Kailua?

Our map will help you find the perfect place to stay in Kailua by showing you the exact location of each vacation rental.