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Kailua vacation rentals

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Best Kailua vacation rentals

Most recommended vacation rentals in Kailua

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Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views - Kailua - Beach
Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views
Kailua, O'ahu, HI
7.7Good(17)
Free Wi-Fi
Pool
$548+
Check availability
Peaceful Hawaii Paradise three minutes from Beautiful Beach - Kailua - Pool
Peaceful Hawaii Paradise three minutes from Beautiful Beach
Kailua, O'ahu, HI
$432+
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Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more - Kailua - Beach
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
Kailua, O'ahu, HI
Pool
Spa
$411+
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Viewhouse In Lanikai Best Location , Lanikai Nuc 90/Bb -0108 - Kailua - Living room
Viewhouse In Lanikai Best Location , Lanikai Nuc 90/Bb -0108
Kailua, O'ahu, HI
Free Wi-Fi
$532+
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Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood- Legal - Kailua
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood- Legal
Kailua, O'ahu, HI
Free Wi-Fi
Pool
$494+
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Lanikai Ohana Hale - Kailua - Beach
Lanikai Ohana Hale
Kailua, O'ahu, HI
9.7Wonderful(14)
$913+
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Tropical Studio w/ pool, spa, a/c, WFH, walk to Kailua Beach (30 day Discount!) - Kailua - Beach
Tropical Studio w/ pool, spa, a/c, WFH, walk to Kailua Beach (30 day Discount!)
Kailua, O'ahu, HI
9.5Wonderful(4)
Free Wi-Fi
Pool
Spa
$230+
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Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa. - Kailua - Living room
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Kailua, O'ahu, HI
Free Wi-Fi
Pool
Spa
$1,951+
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Absolutely Oceanfront - 60' Waterfall Lap Pool - Kailua - Beach
Absolutely Oceanfront - 60' Waterfall Lap Pool
Kailua, O'ahu, HI
Free Wi-Fi
Pool
$676+
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Newly Remodeled And The Best Access To Sandy Lanikai Beach! Nuc # 90/Tvu-0031 - Kailua
Newly Remodeled And The Best Access To Sandy Lanikai Beach! Nuc # 90/Tvu-0031
Kailua, O'ahu, HI
Free Wi-Fi
$3,109+
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kailua great location master bedroom - Kailua
kailua great location master bedroom
Kailua, O'ahu, HI
Free Wi-Fi
Pool
$141+
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Modern Luxury Beach House Kailua - Kailua
Modern Luxury Beach House Kailua
Kailua, O'ahu, HI
9.3Wonderful(46)
Parking
Free Wi-Fi
$656+
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Kailani Loft, Kailua Coconut Grove 1-bedroom - Kailua
Kailani Loft, Kailua Coconut Grove 1-bedroom
Kailua, O'ahu, HI
9.3Wonderful(29)
Parking
Free Wi-Fi
$478+
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Beautiful Guest House Kailua Beach - Kailua
Beautiful Guest House Kailua Beach
Kailua, O'ahu, HI
9.0Wonderful(92)
Parking
Free Wi-Fi
$347+
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Heavenly Hale 2 blocks from the beach, private lanai, off street parking!!! - Kailua
Heavenly Hale 2 blocks from the beach, private lanai, off street parking!!!
Kailua, O'ahu, HI
$145+
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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home - Kailua
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
Kailua, O'ahu, HI
Pool
Spa
$1,236+
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KAYAK’s insights for vacation rentals in Kailua

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Kailua with confidence.

Which month has the cheapest vacation rental rates in Kailua?

Vacation rentals are cheapest in Kailua in December, with average rates of $275. In comparison, October is the most expensive month, with prices at $1,624.

What is the cheapest day of the week to book a vacation rental in Kailua?

Sunday offers the lowest rates in Kailua, with an average nightly price of $194. The highest prices are found on Monday, with average rates at $973.
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Good to know

Low season

December

High season

October

Average price (weeknight)

$563

Average price (weekend night)

$344
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 135% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's 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, 25 reviews), Steps To Beach-Heated Pool-Air Con-Gated Community-Contact Host 1 Week Min Stay (10.0, 33), and Large, beautiful, updated home w/pool, AC,mins from beach in Kailua! Flex stays! (10.0, 23), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Kailua for 7 days.
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FAQs when booking a vacation home in Kailua

  • 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 apartments, bungalows, condos, cottages, houses and villas.

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

    There are many types of properties available for Kailua vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Stay Condominiums Waikiki and Jenny's Cottage Waikiki.

  • 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 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.

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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.

Everything you need to know for your stay in Kailua

Kailua vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Kailua. Find cheap vacation homes to rent in Kailua. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Kailua that suits you best.

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