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Kailua Vacation Rentals

Find 490 available offers from 12 partners
Anytime
1 guest
Anytime
1 guest

Recommended vacation rentals in Kailua

Find your perfect vacation rental in Kailua from just $159 per night!

Apartment Kailua
Mar 19 - Mar 26
Free cancellation
Apartment ∙ 2 guests ∙ 1 bedroom

37 m² Apartment

Kailua, Honolulu County, Hawaii, United States
$322
per night
$322
per night
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House Kailua
Mar 27 - Apr 3
Free cancellation
House ∙ 4 guests ∙ 2 bedrooms

House

Kailua, Honolulu County, Hawaii, United States
$546
per night
$546
per night
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Cottage Kailua
Apr 14 - Apr 21
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage

Kailua, Honolulu County, Hawaii, United States
$784
per night
Excellent(154 ratings)
$784
per night
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House Kailua
Apr 14 - Apr 21
House ∙ 6 guests ∙ 4 bedrooms

116 m² House

Kailua, Honolulu County, Hawaii, United States
$1,173
per night
Outstanding(78 ratings)
$1,173
per night
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House Kailua
Mar 27 - Apr 3
House ∙ 5 guests ∙ 2 bedrooms

House

Kailua, Honolulu County, Hawaii, United States
$970
per night
Outstanding(232 ratings)
$970
per night
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Houseboat Kailua
Jan 19 - Jan 26
Free cancellation
Houseboat ∙ 4 guests ∙ 1 bedroom

Houseboat

Kailua, Honolulu County, Hawaii, United States
$227
per night
Excellent
$227
per night
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House Kailua
-35%
May 4 - May 11
House ∙ 4 guests ∙ 1 bedroom

39 m² House

Kailua, Honolulu County, Hawaii, United States
$1,059$692
per night
Outstanding(97 ratings)
$1,059$692
per night
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House Kailua
Mar 19 - Mar 26
Free cancellation
House ∙ 2 guests ∙ 1 bedroom

37 m² House

Kailua, Honolulu County, Hawaii, United States
$289
per night
$289
per night
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Resort Kailua
-19%
Nov 15 - Nov 22
Free cancellation
Resort ∙ 127 guests ∙ 1 bedroom

Paradise Bay Resort

Kailua, Honolulu County, Hawaii, United States
$414$336
per night
Very good
$414$336
per night
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Cottage Kailua
Apr 1 - Apr 8
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage

Kailua, Honolulu County, Hawaii, United States
$388
per night
(9 ratings)
$388
per night
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House Kailua
House ∙ 10 guests ∙ 5 bedrooms

167 m² House

Kailua, Honolulu County, Hawaii, United States
from $162
per night
Outstanding(9 ratings)
from $162
per night
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House Kailua
House ∙ 10 guests ∙ 5 bedrooms

167 m² House

Kailua, Honolulu County, Hawaii, United States
from $1,495
per night
Outstanding(9 ratings)
from $1,495
per night
View deal
House Kailua
House ∙ 5 guests ∙ 2 bedrooms

88 m² House

Kailua, Honolulu County, Hawaii, United States
from $259
per night
Outstanding(93 ratings)
from $259
per night
View deal
House Kailua
House ∙ 20 guests ∙ 8 bedrooms

465 m² House

Kailua, Honolulu County, Hawaii, United States
from $1,380
per night
Outstanding(85 ratings)
from $1,380
per night
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Cottage Kailua
Cottage ∙ 2 guests ∙ 1 bedroom

56 m² Cottage

Kailua, Honolulu County, Hawaii, United States
from $241
per night
Outstanding(85 ratings)
from $241
per night
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Vacation rentals and apartments with air conditioning

House  Kailua
from $2,791 per night
House ∙ 16 guests ∙ 6 bedrooms
5.0
Outstanding(26 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House  Kailua
from $430 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(31 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House  Kailua
from $173 per night
House ∙ 2 guests ∙ 1 bedroom
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Apartments with a balcony or patio

House  Kailua
from $1,750 per night
House ∙ 4 guests ∙ 1 bedroom
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
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House  Kailua
from $328 per night
House ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent(85 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
View deal
House  Kailua
from $888 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(81 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
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Vacation homes and cottages with a garden

House  Kailua
from $243 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(40 ratings)
Kailua, Honolulu County, Hawaii, United States
Yard
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House  Kailua
from $391 per night
House ∙ 8 guests ∙ 4 bedrooms
Kailua, Honolulu County, Hawaii, United States
Yard
View deal
Cottage  Kailua
from $880 per night
Cottage ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(23 ratings)
Kailua, Honolulu County, Hawaii, United States
Yard
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Best Vacation Home Deals in Kailua

Save up to 11%

Mobile home Kailua
Dec 30 - Jan 6
-11%
$222
$198 per night
Mobile home ∙ 2 guests ∙ 1 bedroom
Kailua, Honolulu County, Hawaii, United States
View deal

Search and compare the 490 vacation homes listed in Kailua and find a great place for a relaxing vacation. HomeToGo instantaneously highlights the best offers by comparing all of the available vacation homes in Kailua from its various partners.

Budget-friendly Rentals in Kailua

Find Fantastic yet Inexpensive Rentals

House Kailua
from $363 per night
House ∙ 7 guests ∙ 3 bedrooms
4.8
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
from $497 per night
House ∙ 5 guests ∙ 2 bedrooms
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from $671 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(11 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal

Top-Rated Offers and Accommodations in Kailua

Book Vacation Rentals with the Highest User Rating

House Kailua
from $294 per night
House ∙ 5 guests ∙ 2 bedrooms
4.7
Excellent(95 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from $571 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding(70 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from $946 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding(60 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal

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Popular Rental Amenities in Kailua

  • Pool (153)
  • WiFi (461)
  • Air conditioning (409)
  • Kitchen (482)
  • TV (437)
  • Parking (38)
  • Balcony/patio (175)
  • Washing machine (281)
  • Grill (219)
  • Microwave (423)
  • No smoking (458)
  • Pet-friendly (41)

One-third of the vacation homes offer a pool, which makes Kailua an excellent vacation destination for vacationers looking to spend vacation poolside. Additionally, more apartment rental have a pool than cottage. Most of the apartment rental with pools in Kailua accommodate 4 guests and have an average cost of $1,804 per night. If you would ideally like to be close to the water, nearly half of the vacation homes providing a pool are located within 2 kilometres of the waterfront.

Soak up Paradise at your Kailua vacation house

It's practically impossible to find a Kailua vacation home without a good view. Whether you have a balcony overlooking the azure waters of the Pacific Ocean or a front door opening onto a luxurious pool, you'll be able to easily enjoy Hawaii's gorgeous landscape and warm temperatures. When you're tired of all the beach time, Kailua has plenty to keep you busy: markets, restaurants, bars, and adorable boutique shops abound.

What are the must-see attractions in Kailua?

Sightseeing in Kailua

Kailua Beach Park

Clear water and pristine white sand make this beach park the perfect place for water sports and aquatic activities. Rent some snorkel gear and look for tropical fish, or grab a kayak and hit the calm waves.

Lanikai Beach

Lanikai means "heavenly sea," and there's no better description for a beach such as this one. Although it's less than a mile long, Lanikai Beach is dubbed one of the best beaches in the world. You'll understand why when you see it.

Lanikai Pillboxes

The Lanikai Pillbox Hike is a moderately difficult but insanely scenic hiking trail with sweeping vistas overlooking the ocean and Kailua's unique landscape. You'll need about 90 minutes to complete this trail, and you'll definitely want to bring your camera.

Kalama Beach Park

Also known as Boettcher Estate, the Kalama Beach Park has the same white sands and turquoise waters of Kailua Beach. This beach is especially popular among windsurfers, bodyboarders, and kitesurfers. If that's not your thing, feel free to relax on the beach with a good book.

Olomana Three Peaks Trail

Olomana Three Peaks Trail is a challenging, rugged hike, but the rewards are well worth it. Thrill seekers, take note: the narrow path sometimes plunges to dramatic depths up to 1,600 feet on each side. Take in the views, but be careful with your footing.

Information about vacation rentals in Kailua

🏡 Vacation rentals available 490 rentals
💳 Possible discounts up to 11%
🌙 Nightly prices starting at $159
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 40 homes
🏊 Vacation rentals with pools 152 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Kailua?

September has the highest availability of House rental in Kailua, so you can expect a lot of vacation rentals available, even for last-minute bookings.

What are the most popular vacation home amenities in Kailua?

Many travellers are searching for Pool, Internet, and Air conditioning when booking a vacation home in Kailua.

Are there pet-friendly vacation rentals in Kailua?

Yes, there are 40 pet-friendly vacation rentals in Kailua, with an average nightly price of $1,191.

What's the best month to visit Kailua?

When booking a vacation rental in Kailua, remember that the rainiest months are usually May and July, with November often being the sunniest.

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