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Kailua Vacation Rentals

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Top 15 Recommended vacation rentals in Kailua

Find your perfect vacation rental in Kailua from just $180 per night!

House Kailua
House ∙ 5 guests ∙ 2 bedrooms

88 m² House

Kailua, Honolulu County, Hawaii, United States
from $243
per night
Outstanding(96 ratings)
from $243
per night
View deal
Cabin Kailua
Cabin ∙ 2 guests ∙ 1 bedroom

56 m² Cabin

Kailua, Honolulu County, Hawaii, United States
from $212
per night
Outstanding(88 ratings)
from $212
per night
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House Kailua
House ∙ 5 guests ∙ 2 bedrooms

House

Kailua, Honolulu County, Hawaii, United States
from $894
per night
Outstanding(242 ratings)
from $894
per night
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House Kailua
House ∙ 20 guests ∙ 8 bedrooms

465 m² House

Kailua, Honolulu County, Hawaii, United States
from $1,501
per night
Outstanding(87 ratings)
from $1,501
per night
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House Kailua
House ∙ 14 guests ∙ 8 bedrooms

465 m² House

Kailua, Honolulu County, Hawaii, United States
from $3,282
per night
Excellent(104 ratings)
from $3,282
per night
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House Kailua
House ∙ 6 guests ∙ 3 bedrooms

186 m² House

Kailua, Honolulu County, Hawaii, United States
from $907
per night
Excellent(173 ratings)
from $907
per night
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House Kailua
House ∙ 18 guests ∙ 6 bedrooms

417 m² House

Kailua, Honolulu County, Hawaii, United States
from $1,545
per night
from $1,545
per night
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Villa Kailua
Villa ∙ 12 guests ∙ 5 bedrooms

Villa

Kailua, Honolulu County, Hawaii, United States
from $681
per night
from $681
per night
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House Kailua
House ∙ 8 guests ∙ 4 bedrooms

325 m² House

Kailua, Honolulu County, Hawaii, United States
from $952
per night
Outstanding(61 ratings)
from $952
per night
View deal
Apartment Kailua
Apartment ∙ 2 guests ∙ 1 bedroom

30 m² Apartment

Kailua, Honolulu County, Hawaii, United States
from $220
per night
Outstanding(45 ratings)
from $220
per night
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Bed and breakfast Kailua
Bed and breakfast ∙ 3 guests ∙ 4 bedrooms

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

Kailua, Honolulu County, Hawaii, United States
from $492
per night
Excellent(135 ratings)
from $492
per night
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House Kailua
House ∙ 4 guests ∙ 2 bedrooms

84 m² House

Kailua, Honolulu County, Hawaii, United States
from $591
per night
Outstanding(4 ratings)
from $591
per night
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House Kailua
House ∙ 6 guests ∙ 3 bedrooms

210 m² House

Kailua, Honolulu County, Hawaii, United States
from $790
per night
Excellent(30 ratings)
from $790
per night
View deal
Apartment Kailua
Apartment ∙ 3 guests ∙ 1 bedroom

37 m² Apartment

Kailua, Honolulu County, Hawaii, United States
from $184
per night
Outstanding(26 ratings)
from $184
per night
View deal
House Kailua
House ∙ 2 guests ∙ 1 bedroom

44 m² House

Kailua, Honolulu County, Hawaii, United States
from $1,081
per night
Excellent(183 ratings)
from $1,081
per night
View deal

Vacation rentals and apartments with air conditioning

House  Kailua
from $885 per night
House ∙ 4 guests ∙ 1 bedroom

39 m² House

4.8
Outstanding(147 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House  Kailua
from $1,605 per night
House ∙ 10 guests ∙ 5 bedrooms

House

4.9
Outstanding(52 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Apartment  Kailua
from $246 per night
Apartment ∙ 4 guests ∙ 1 bedroom

74 m² Apartment

4.9
Outstanding(18 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Best vacation rentals with a balcony

Apartment  Kailua
from $690 per night
Apartment ∙ 2 guests ∙ 1 bedroom

47 m² Apartment

4.7
Excellent(185 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
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House  Kailua
from $1,001 per night
House ∙ 8 guests ∙ 4 bedrooms

203 m² House

Kailua, Honolulu County, Hawaii, United States
Balcony
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House  Kailua
from $1,620 per night
House ∙ 6 guests ∙ 3 bedrooms

139 m² House

5.0
Outstanding(82 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony
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Vacation rentals with a fireplace

House  Kailua
from $553 per night
House ∙ 6 guests ∙ 3 bedrooms

232 m² House

Kailua, Honolulu County, Hawaii, United States
Fireplace
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House  Kailua
from $3,715 per night
House ∙ 14 guests ∙ 5 bedrooms

293 m² House

5.0
Outstanding(149 ratings)
Kailua, Honolulu County, Hawaii, United States
Fireplace
View deal
Bed and breakfast  Kailua
from $830 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom

La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)

4.9
Outstanding(13 ratings)
Kailua, Honolulu County, Hawaii, United States
Fireplace
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Budget-friendly Rentals in Kailua

Find Fantastic yet Inexpensive Rentals

Cabin Kailua
from $315 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

70 m² Cabin

4.9
Outstanding(84 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from $1,434 per night
House ∙ 14 guests ∙ 4 bedrooms

306 m² House

5.0
Outstanding(31 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
Apartment Kailua
from $201 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment

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 $1,338 per night
House ∙ 8 guests ∙ 4 bedrooms

297 m² House

5.0
Outstanding(131 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
Apartment Kailua
from $263 per night
Apartment ∙ 2 guests ∙ 1 bedroom

56 m² Apartment

5.0
Outstanding(130 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal
House Kailua
from $770 per night
House ∙ 7 guests ∙ 3 bedrooms

House

4.9
Outstanding(39 ratings)
Kailua, Honolulu County, Hawaii, United States
View deal

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Popular Rental Amenities in Kailua

  • Pool (104)
  • WiFi (257)
  • Air conditioning (225)
  • Kitchen (255)
  • TV (240)
  • Parking (24)
  • Balcony/patio (158)
  • Washing machine (239)
  • Grill (188)
  • Microwave (231)
  • No smoking (251)
  • Pet-friendly (19)

Nearly half 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 3 guests and have an average cost of $1,975 per night. If you would ideally like to be close to the water, many of the vacation homes providing a pool are located within 2 kilometres of the waterfront.

Price and Availability Index in Kailua

Click on any bar to see price and availability information

Vacation Rental Price Information in Kailua

The graph shows average prices of rentals in Kailua for the next twelve months. The most expensive week to book a vacation rental in Kailua is in September (9/5 – 9/12). The cheapest week to book a vacation rental is in November (11/22 – 11/29).

Rental availability information in Kailua

Check how busy Kailua is with our availability graph. The week with the highest booking rate is in October (10/10 – 10/17). Only 23% of the rentals are still available. The week with the most available rentals is in November (11/22 – 11/29), with 80% of the vacation rentals available.

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 261 rentals
🌙 Nightly prices starting at $180
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 19 homes
🏊 Vacation rentals with pools 104 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Kailua?

November 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 19 pet-friendly vacation rentals in Kailua, with an average nightly price of $1,079.

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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