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Kailua holiday homes and lettings

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Top 15 Recommended holiday lettings in Kailua

Find your perfect holiday home, apartment or cottage in Kailua from just £53 per night!

House Kailua
House ∙ 10 guests ∙ 5 bedrooms

Holiday home with private pool, hot tub & barbeque | Suitable for remote work

Kailua, Honolulu County, Hawaii, United States
from £842
per night
Outstanding(11 ratings)
Vrbo
from £842
per night
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Vrbo
House Kailua
House ∙ 5 guests ∙ 2 bedrooms

Holiday home with garden, terrace & barbecue | City view

Kailua, Honolulu County, Hawaii, United States
from £135
per night
Outstanding(94 ratings)
Vrbo
from £135
per night
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Vrbo
Cottage Kailua
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with garden, terrace & barbeque

Kailua, Honolulu County, Hawaii, United States
from £157
per night
Outstanding(150 ratings)
Vrbo
from £157
per night
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Vrbo
House Kailua
House ∙ 6 guests ∙ 4 bedrooms

Child-friendly house with garden, terrace & BBQ

Kailua, Honolulu County, Hawaii, United States
from £556
per night
Outstanding(87 ratings)
Vrbo
from £556
per night
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Vrbo
House Kailua
House ∙ 9 guests ∙ 3 bedrooms

Family-friendly holiday home with BBQ, terrace & garden | Next to the beach

Kailua, Honolulu County, Hawaii, United States
from £278
per night
Very good(73 ratings)
Vrbo
from £278
per night
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Vrbo
Bed and breakfast Kailua
Bed and breakfast ∙ 3 guests ∙ 4 bedrooms

Bed & breakfast with garden, jacuzzi & terrace

Kailua, Honolulu County, Hawaii, United States
from £272
per night
Excellent(103 ratings)
Vrbo
from £272
per night
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Vrbo
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with garden & terrace | Mountain view

Kailua, Honolulu County, Hawaii, United States
from £548
per night
Excellent(161 ratings)
Vrbo
from £548
per night
View deal
Vrbo
House Kailua
House ∙ 10 guests ∙ 5 bedrooms

House with barbecue, garden & terrace

Kailua, Honolulu County, Hawaii, United States
from £830
per night
Outstanding(46 ratings)
Vrbo
from £830
per night
View deal
Vrbo
House Kailua
House ∙ 4 guests ∙ 1 bedroom

House with terrace, barbecue & garden | Mountain view

Kailua, Honolulu County, Hawaii, United States
from £359
per night
Outstanding(95 ratings)
Vrbo
from £359
per night
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Vrbo
Cottage Kailua
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with garden, BBQ & terrace | Close to the beach

Kailua, Honolulu County, Hawaii, United States
from £80
per night
Outstanding(86 ratings)
Vrbo
from £80
per night
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Vrbo
House Kailua
House ∙ 20 guests ∙ 8 bedrooms

Child-friendly pleasant house with terrace, garden & private pool | Beach nearby | Good for workation

Kailua, Honolulu County, Hawaii, United States
from £777
per night
Outstanding(85 ratings)
Vrbo
from £777
per night
View deal
Vrbo
Cottage Kailua
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage with terrace, barbeque & jacuzzi

Kailua, Honolulu County, Hawaii, United States
from £369
per night
Excellent(172 ratings)
Vrbo
from £369
per night
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Vrbo
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented holiday home with garden, barbeque & terrace

Kailua, Honolulu County, Hawaii, United States
from £278
per night
Outstanding(79 ratings)
Vrbo
from £278
per night
View deal
Vrbo
House Kailua
House ∙ 8 guests ∙ 5 bedrooms

Holiday home with garden, terrace & BBQ | Mountain view

Kailua, Honolulu County, Hawaii, United States
from £296
per night
Outstanding(51 ratings)
Vrbo
from £296
per night
View deal
Vrbo
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly house with terrace, private pool & hot tub | Mountain view | Suitable for remote work

Kailua, Honolulu County, Hawaii, United States
from £448
per night
Outstanding(118 ratings)
Vrbo
from £448
per night
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Vrbo

Holiday lettings and apartments with air conditioning

House  Kailua
from £235 per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, garden & barbeque

5.0
Outstanding(34 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
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Villa  Kailua
from £457 per night
Villa ∙ 8 guests ∙ 4 bedrooms

Family-oriented lovely villa with barbecue & private pool | Beach nearby | Suitable for remote work

5.0
Outstanding(3 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Apartment  Kailua
from £139 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Children-friendly charming flat with terrace, BBQ & garden | Mountain view

4.8
Outstanding(70 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
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Best holiday homes with a patio or terrace

House  Kailua
from £457 per night
House ∙ 2 guests ∙ 1 bedroom

House with pool, terrace & BBQ

4.7
Excellent(182 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
Vrbo
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House  Kailua
from £262 per night
House ∙ 3 guests ∙ 1 bedroom

House with terrace, pool & garden

4.9
Outstanding(126 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
Vrbo
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Apartment  Kailua
from £360 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with terrace, garden & BBQ | Beach nearby

5.0
Outstanding(70 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
Vrbo
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Best holiday rentals with a balcony

House  Kailua
from £443 per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly pleasant holiday home with garden & barbecue | Nature view | Close to the beach

5.0
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
Vrbo
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Cottage  Kailua
from £206 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with terrace, garden & barbeque

4.7
Excellent(66 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
Vrbo
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Apartment  Kailua
from £412 per night
Apartment ∙ 2 guests ∙ 2 bedrooms

Pleasant holiday apartment with garden, pool & BBQ

4.7
Excellent(174 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
Vrbo
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Budget-friendly Holiday Homes in Kailua

Find Fantastic yet Cheap Lettings

House Kailua
from £1,699 per night
House ∙ 14 guests ∙ 8 bedrooms

Child-friendly house with terrace, private pool & garden | Nature view | Beach nearby

4.7
Excellent(104 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
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House Kailua
from £1,486 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with terrace, barbeque & garden | Nature view

5.0
Outstanding(21 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
View deal
Apartment Kailua
from £102 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Family-friendly holiday apartment with garden, BBQ & terrace | Mountain view | Beach nearby

5.0
Outstanding(17 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
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Top-Rated Lettings and Properties in Kailua

Book Holiday Letting Offers with the Highest User Rating

Apartment Kailua
from £410 per night
Apartment ∙ 2 guests ∙ 2 bedrooms

Holiday apartment with garden

4.9
Outstanding(288 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
View deal
House Kailua
from £665 per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly nice house with garden, private pool & barbecue

4.9
Outstanding(164 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
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House Kailua
from £505 per night
House ∙ 12 guests ∙ 4 bedrooms

House with garden, terrace & barbecue

4.7
Excellent(106 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
View deal

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Spend your budget exactly as planned by comparing thousands of providers.

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Transform holiday planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of holiday homes.

Popular holiday rental amenities in Kailua

  • Pool (138)
  • WiFi (427)
  • Air conditioning (379)
  • Kitchen (442)
  • TV (410)
  • Balcony/patio (164)
  • Parking (33)
  • Garden (296)
  • Washing machine (396)
  • Hot tub (53)
  • Grill (210)
  • Microwave (403)

Kailua is a great holiday destination if you want to rent a holiday home with a pool. One-third of the accommodation options here have this amenity. More apartment rental have a pool than cottage. Most of the apartment rental with pools in Kailua accommodate 3 holidaymakers and cost £1,156 a night. You can also choose a holiday home providing a pool near the water, which is the case for more than half of the properties there.

Price and Availability Index for Kailua

Click on any bar to see price and availability information

Holiday Letting Price Information in Kailua

This graph displays the average prices for the next twelve months in Kailua. The week with the highest average prices is in January (03/01 – 10/01). During this week, a night will cost you £415 on average. Kailua is cheaper during one week in June (21/06 – 28/06), when prices are on average £393 a night.

Rental availability information in Kailua

Check how busy Kailua is with our availability graph. So far, the week with the least available rentals in Kailua is in May (02/05 – 09/05). Conversely, you will find the highest percentage of available offers in Kailua in October (25/10 – 01/11).

Soak up paradise at your Kailua holiday accommodation

It's practically impossible to find Kailua holiday accommodation 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 holiday rentals in Kailua

🏡 Holiday homes available 453 rentals
🌙 Nightly prices from £53
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly rentals 35 properties
🏊 Holiday rentals with pools 138 properties
10,030 reviews
Kailua holiday rentals have an average rating of 4.9/5 across 10,030 reviews left by travellers.

Frequently Asked Questions

What is the price per night for a holiday rental in Kailua?

The nightly price in Kailua is £53 on average. The average rate for renting a apartment rental is £212 per night. House rentals will be £872 per night.

How many holiday lettings are available to book in Kailua?

Currently there are 453 holiday homes from 10 providers on offer in Kailua.

What is the most searched holiday home amenity in Kailua?

Travellers planning trips to Kailua usually search for Pool, Internet, and Air conditioning when it comes to holiday home amenities.

How many holiday homes with a pool there are on offer in Kailua?

Holiday rentals with pools are 30 of all offers in Kailua. In addition, there are 54 of apartments with pools near water.

Can i bring my pet while staying in an accommodation in Kailua?

Dogs are welcome in Kailua which is home to 35 pet-friendly holiday rentals.

What is the perfect time to travel to Kailua?

August and September are the best months for sun lovers in Kailua.

Can you get discounts on holiday accommmodation in Kailua?

You can find fabulous discounts on holiday rentals in Kailua with prices for a letting beginning at £53 - and HomeToGo has created plenty of filters that mean it's quick and simple to locate some awesome offers. If you don't have set dates for your holiday, try a search using HomeToGo's flexible dates technology to easily look for low-price timings and see discounts of up to 10%. Additionally, HomeToGo's 'distance from' filter can help you uncover top quality accommodation offers in great value, under-the-radar locales with good proximity to the area of your choice, whether that's sand and sea, a mountain for snowboarding, or a city's urban hub. Book early to get the benefits of a wide range of offers and low prices - and do so without worries by selecting HomeToGo's 'free cancellation' filter when using the website or app.

What are the advantages of booking a holiday letting in Kailua with HomeToGo?

From increased privacy away from the crowds to more space in which to chill out with your loved ones, holiday rentals in Kailua have plenty of advantages. HomeToGo shows you genuine ratings from verified visitors, and searching is secure, easy, and stress-free - so with 453 lets from 10 providers in the region, you're guaranteed to discover the right holiday home with the amenities and features you need in Kailua.

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