Holiday homes & rentals in Kailua - HomeToGo base64Hash Holiday homes & rentals in Kailua - HomeToGo

Holiday homes & rentals in Kailua

Find 262 available offers from 9 partners
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Top 15 Recommended holiday lettings in Kailua

Find your perfect holiday home, apartment or cottage in Kailua from just £87 per night!

House Kailua
House ∙ 2 guests ∙ 1 bedroom

Wonderful holiday home with terrace & garden | Suitable for remote work

Kailua, Honolulu County, Hawaii, United States
This house rental in Kailua offers beach access, a garden, a kitchen, and parking, perfect for a relaxing getaway for two.
from £212
per night
Outstanding(39 ratings)
from £212
per night
View deal
Villa Kailua
Villa ∙ 12 guests ∙ 5 bedrooms

Villa with garden, terrace & BBQ

Kailua, Honolulu County, Hawaii, United States
This villa in Kailua offers a spa, kitchen, garden, and parking, perfect for family gatherings of up to 12 guests.
from £423
per night
from £423
per night
View deal
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 £900
per night
Outstanding(12 ratings)
from £900
per night
View deal
House Kailua
House ∙ 4 guests ∙ 1 bedroom

House with garden, barbecue & private pool | Mountain view

Kailua, Honolulu County, Hawaii, United States
This house rental in Kailua features a private pool, garden, mountain views, and a kitchen, perfect for a family getaway.
from £467
per night
Outstanding(155 ratings)
from £467
per night
View deal
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with garden & terrace | Mountain view

Kailua, Honolulu County, Hawaii, United States
This house rental in Kailua offers a garden, mountain view, beach access, and space for six, perfect for a memorable family getaway.
from £568
per night
Excellent(175 ratings)
from £568
per night
View deal
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with garden & barbeque

Kailua, Honolulu County, Hawaii, United States
This house rental in Kailua features a kitchen, garden, and parking, perfect for a getaway with friends or family.
from £142
per night
Outstanding(2 ratings)
from £142
per night
View deal
House Kailua
House ∙ 11 guests ∙ 5 bedrooms

House with garden, private pool & BBQ

Kailua, Honolulu County, Hawaii, United States
This Kailua house rental features a private pool, garden, and balcony, accommodating up to 11 guests for a memorable getaway.
from £766
per night
Outstanding(2 ratings)
from £766
per night
View deal
House Kailua
House ∙ 7 guests ∙ 4 bedrooms

House with jacuzzi, barbeque & terrace

Kailua, Honolulu County, Hawaii, United States
This family-friendly house in Kailua features a private pool, hot tub, and garden, perfect for a relaxing getaway for seven.
from £532
per night
Outstanding(10 ratings)
from £532
per night
View deal
House Kailua
House ∙ 6 guests ∙ 3 bedrooms

House with hot tub, barbeque & private pool | City view | Suitable for remote work

Kailua, Honolulu County, Hawaii, United States
This Kailua house rental features a private pool, hot tub, garden, and a fireplace, perfect for family getaways.
from £463
per night
Outstanding(83 ratings)
from £463
per night
View deal
Cottage Kailua
Cottage ∙ 2 guests ∙ 1 bedroom

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

Kailua, Honolulu County, Hawaii, United States
This cottage in Kailua features a kitchen, garden, and parking, perfect for a serene getaway for two.
from £101
per night
Outstanding(89 ratings)
from £101
per night
View deal
Cottage Kailua
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with terrace, BBQ & garden

Kailua, Honolulu County, Hawaii, United States
This cottage in Kailua features a garden and parking, perfect for a romantic getaway for two amidst stunning surroundings.
from £107
per night
Outstanding(65 ratings)
from £107
per night
View deal
Cottage Kailua
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with terrace, garden & barbeque | Nature view

Kailua, Honolulu County, Hawaii, United States
This cottage in Kailua offers a kitchen, balcony, garden, and waterside views, perfect for a family getaway.
from £185
per night
Excellent(67 ratings)
from £185
per night
View deal
House Kailua
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped charming holiday home with garden, private pool & BBQ | Close to the beach

Kailua, Honolulu County, Hawaii, United States
This house rental in Kailua features a private pool, hot tub, garden, and direct beach access, perfect for a memorable getaway.
from £272
per night
Outstanding(4 ratings)
from £272
per night
View deal
Cottage Kailua
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with terrace, garden & barbeque

Kailua, Honolulu County, Hawaii, United States
This cottage in Kailua features a kitchen, garden, and parking, perfect for a tranquil getaway for two.
from £103
per night
Outstanding(55 ratings)
from £103
per night
View deal
House Kailua
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented lovely house with BBQ, terrace & garden | Pet-friendly

Kailua, Honolulu County, Hawaii, United States
This family-friendly house rental in Kailua features a garden, kitchen, and parking, perfect for six with pets welcome.
from £126
per night
Outstanding(154 ratings)
from £126
per night
View deal

Holiday lettings and apartments with air conditioning

House  Kailua
from £460 per night
House ∙ 4 guests ∙ 1 bedroom

House with barbeque, private pool & garden | Garden view

4.8
Outstanding(155 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
View deal
House  Kailua
from £726 per night
House ∙ 15 guests ∙ 6 bedrooms

House with terrace, garden & BBQ | Mountain view | Perfect for remote work

5.0
Outstanding(8 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
View deal
House  Kailua
from £398 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday home with barbeque, garden & terrace | Close to the beach | Good for workation

5.0
Outstanding(43 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
View deal
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Best holiday rentals with a balcony

Apartment  Kailua
from £462 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Pleasant holiday apartment with garden, pool & BBQ

4.8
Outstanding(186 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
View deal
House  Kailua
from £225 per night
House ∙ 4 guests ∙ 2 bedrooms

House with terrace, barbeque & garden | Nature view

Kailua, Honolulu County, Hawaii, United States
Balcony
View deal
House  Kailua
from £508 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, barbecue & terrace

Kailua, Honolulu County, Hawaii, United States
Balcony
View deal
See all offers

Most popular holiday lettings with a fireplace

House  Kailua
from £810 per night
House ∙ 9 guests ∙ 4 bedrooms

Fully equipped holiday home with BBQ, private pool & hot tub | Close to the beach

4.5
Excellent(4 ratings)
Kailua, Honolulu County, Hawaii, United States
Fireplace
View deal
House  Kailua
from £1,882 per night
House ∙ 14 guests ∙ 5 bedrooms

Fully equipped spacious house with terrace, garden & BBQ | Close to the beach

5.0
Outstanding(151 ratings)
Kailua, Honolulu County, Hawaii, United States
Fireplace
View deal
House  Kailua
from £294 per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped house with barbecue, terrace & heated pool | Mountain view

Kailua, Honolulu County, Hawaii, United States
Fireplace
View deal
See all offers

Budget-friendly Holiday Homes in Kailua

Find Fantastic yet Cheap Lettings

Cottage Kailua
from £370 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage with terrace, barbeque & jacuzzi

4.7
Excellent(192 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from £713 per night
House ∙ 7 guests ∙ 3 bedrooms

Children-friendly lovely house with terrace, barbecue & private pool | Mountain view

5.0
Outstanding(72 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from £3,239 per night
House ∙ 18 guests ∙ 6 bedrooms

Children-friendly house with private pool, garden & BBQ | Mountain view | Beach nearby | Suitable for remote work | Pet-friendly

5.0
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal

Top-Rated Lettings and Properties in Kailua

Book Holiday Letting Offers with the Highest User Rating

House Kailua
from £190 per night
House ∙ 2 guests ∙ 1 bedroom

Fully equipped house with BBQ & garden | City view

5.0
Outstanding(42 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
Apartment Kailua
from £178 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with barbeque | Nature view

4.7
Excellent(36 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from £666 per night
House ∙ 14 guests ∙ 7 bedrooms

House with terrace, jacuzzi & private pool

5.0
Outstanding(35 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal

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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 (97)
  • WiFi (247)
  • Air conditioning (215)
  • Kitchen (248)
  • TV (234)
  • Balcony/patio (153)
  • Parking (22)
  • Garden (168)
  • Washing machine (234)
  • Hot tub (48)
  • Grill (185)
  • Microwave (226)

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 4 holidaymakers and cost £1,089 a night. You can also choose a holiday home providing a pool near the water, which is the case for many 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 December (19/12 – 26/12). During this week, a night will cost you £979 on average. Kailua is cheaper during one week in September (12/09 – 19/09), when prices are on average £824 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 February (20/02 – 27/02). Conversely, you will find the highest percentage of available offers in Kailua in August (01/08 – 08/08).

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 262 rentals
🌙 Nightly prices from £87
⭐ Popular amenities Pool, Internet and Air conditioning
🏊 Holiday rentals with pools 94 properties

Frequently Asked Questions

What is the average nightly rate for a holiday rental in Kailua?

The average starting price for a holiday cottage or rental in Kailua is £87 per night. Whether you're after something simple or more luxurious, there's a wide range available. Check HomeToGo to see current rates and discounts.

How many holiday cottages are available to rent in Kailua? And what are the most popular types of holiday lets?

There are 262 holiday lettings from 9 providers on offer in Kailua. Many of holiday rentals in Kailua are house rentals, making them a top pick among travellers. These are perfect for groups of around 8 people, offering comfort and flexibility. Discover the most booked options quickly with HomeToGo’s smart filters.

What is the most searched holiday apartment amenity in Kailua?

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

Do you offer holiday homes with a swimming pool in Kailua?

Looking for a pool? You’ll find that many of holiday cottages and homes in Kailua have one. Whether you’re travelling with kids or just want a splash, you’re sorted with 94 options available. Find your perfect poolside getaway on HomeToGo.

Are there any pet-friendly holiday cottages in Kailua?

Travelling with a pet? You’ll find 14 pet-friendly holiday homes in Kailua to choose from. So your furry friend doesn’t have to miss out on the adventure. Easily find your ideal pet-friendly holiday letting on HomeToGo.

What's the best time of year to travel to Kailua?

August and September are usually the warmest months in Kailua, while December and November have the least rain.

Can you get deals on holiday accommmodation in Kailua?

You can find brilliant bargains on holiday lettings in Kailua with the nightly price of a rental starting at just £87 - and HomeToGo has introduced a range of features that mean it's quick and simple to find the best offers. If you're still selecting dates for your holiday, search with HomeToGo's flexible dates technology to quickly locate low-price time periods and see discounts of as much as 10%. In addition, HomeToGo's 'distance from' filter makes it easy to uncover hidden treasure holiday rentals in lower-price, lesser-known spots which are still near to your desired destination, whether that's the coastline, a swimming lake, winter sports area or town centre. Book early to make the most of a wide range of offers and top discounts - and do so without worries by utilising HomeToGo's 'free cancellation' filter when searching for holiday accommodation.

What are the pros of finding a holiday letting in Kailua with HomeToGo?

From increased privacy away from the crowds to more space in which to chill out with your travel companions, holiday lettings in Kailua have a wide range of bonuses. HomeToGo lets you read real reviews from verified visitors, and searching is secure, simple, and hassle-free - so with 262 rentals from 9 providers in the area, you're bound to discover the ideal holiday home with all of the amenities to suit you in Kailua.

Do you offer holiday accommodation for couples in Kailua?

Absolutely – you’ll find plenty of cosy, well-rated holiday lettings in Kailua perfect for two. Enjoy a romantic retreat with just the right amount of space and charm. Find your perfect base with HomeToGo.

Can I book a waterfront holiday rental in Kailua?

Yes, you’ll find 262 holiday rentals near the water in Kailua, whether it’s a beach, lake or river. These spots are perfect for a morning coffee with a view or lazy days by the water. Book with HomeToGo for a stay just steps from the water.

Why should I book my holiday rental with HomeToGo?

HomeToGo offers over 15 million holiday rentals worldwide, so there’s something for everyone. Our smart search makes it easy to find what suits you. Discover your ideal holiday home with ease on HomeToGo.

Can I find family-friendly holiday lettings in Kailua?

Holiday cottages in Kailua are a great fit for families, offering comfort, space and handy amenities. You’ll find options for every budget and family size. Use HomeToGo to explore family-friendly holiday cottages with ease.

Can I cancel my holiday rental booking for free?

Free cancellation is available on lots of holiday homes, depending on the provider. Look for rentals with free cancellation to keep things stress-free.

Is it possible to rent a holiday home for a weekend getaway in Kailua?

Short stays are absolutely possible in Kailua, including weekends. It’s perfect for a quick break without using too many holiday days. HomeToGo helps you spot the best weekend-friendly options fast.

Are there any last-minute holiday rental deals in Kailua?

Need a quick break? Last-minute holiday is just a few clicks away in Kailua. Perfect for a spur-of-the-moment trip — especially with savings of up to 10%. Check today’s offers and grab a holiday cottage at a great price.

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