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Kailua Vacation Rentals

Find 350 available offers from 9 partners
Kailua
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

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.

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Best Vacation Home Deals in Kailua

Save up to 34%

Apartment Kailua
Nov 7 - Nov 14
-24%
$560
$423 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Kailua with Secret Garden
4.9
Outstanding (104 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
Jan 27 - Feb 3
-34%
$1,011
$668 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Kailua with Botanical Garden + Beach Nearby
5.0
Outstanding (57 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 7 - Nov 14
-21%
$798
$627 per night
House ∙ 5 guests ∙ 2 bedrooms
Pleasant Vacation Home in Kuliouou - Kalani Iki with Yard & Grill + Ocean Views
5.0
Outstanding (119 ratings)
Kailua, Honolulu County, Hawaii, United States
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Search through the 350 vacation rentals featured in Kailua and discover a welcoming place for your getaway. HomeToGo instantaneously presents you with the best offers by comparing all of the available properties in Kailua from 8 different providers.

Top-Rated Offers and Accommodations in Kailua

Book Vacation Rentals with the Highest User Rating

Cottage Kailua
Feb 24 - Mar 2
$536 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Kailua with Yard & Grill
4.9
Outstanding (123 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
Aug 3 - Aug 10
$189 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Kailua with Yard & Grill
4.9
Outstanding (116 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 18 - Nov 25
$1,095 per night
House ∙ 6 guests ∙ 4 bedrooms
House in Kailua with Botanical Garden
4.8
Outstanding (57 ratings)
Kailua, Honolulu County, Hawaii, United States
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Recommended Vacation Rentals in Kailua

Find your perfect vacation rental in Kailua: from $162 per night

Bed and breakfast Kailua
May 11 - May 18
$602 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Kailua with Yard + Panoramic View
5.0
Outstanding (111 ratings)
Kailua, Honolulu County, Hawaii, United States
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Cottage Kailua
May 11 - May 18
$870 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Rental Cottage in Kailua with Grill & Yard + Ocean Views
4.9
Outstanding (55 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 25 - Dec 2
$551 per night
House ∙ 3 guests ∙ 1 bedroom
House in Kailua with Outdoor Garden
4.9
Outstanding (99 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
May 11 - May 18
$521 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Apartment in Kailua with Beautiful Pool
4.8
Outstanding (113 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 18 - Nov 25
$537 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Kailua with Grill
4.7
Excellent (79 ratings)
Kailua, Honolulu County, Hawaii, United States
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Cottage Kailua
Feb 24 - Mar 2
$740 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Kailua with Beautiful Pool
4.7
Excellent (113 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
May 11 - May 18
$659 per night
House ∙ 4 guests ∙ 1 bedroom
Vacation Home in Kailua with Botanical Garden
4.6
Excellent (66 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Jan 27 - Feb 3
$1,543 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Kailua with Endless Pool + Next to Beach
4.8
Outstanding (10 ratings)
Kailua, Honolulu County, Hawaii, United States
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Cottage Kailua
May 11 - May 18
$846 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Kailua + Ocean View
4.8
Outstanding (72 ratings)
Kailua, Honolulu County, Hawaii, United States
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Budget-friendly Rentals in Kailua

Find Fantastic yet Inexpensive Rentals

Apartment Kailua
Jun 29 - Jul 6
$406 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Wonderful Apartment in Kuliouou - Kalani Iki with Grill + Ocean Views
4.9
Outstanding (151 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Jan 13 - Jan 20
$1,169 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Kuliouou - Kalani Iki with Grill + Spectacular Views
4.8
Outstanding (129 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 18 - Nov 25
$2,000 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Kaneohe with Yard & Grill + Ocean Views
5.0
Outstanding (1 rating)
Kailua, Honolulu County, Hawaii, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Kailua and book a vacation rental with air conditioning.

House Kailua
$227 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Kailua with Yard & Grill
4.8
Outstanding (28 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House Kailua
$308 per night
House ∙ 7 guests ∙ 3 bedrooms
Family Friendly House in Kailua with Pool
5.0
Outstanding (2 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House Kailua
$227 per night
House ∙ 4 guests ∙ 2 bedrooms
Large Vacation Home in Hawaii Kai with Quiet Pool
4.9
Outstanding (52 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Kailua accommodation with high-speed internet.

House Kailua
$1,323 per night
House ∙ 16 guests ∙ 8 bedrooms
Gorgeous House in Kailua with Pool, Yard & Grill
4.8
Outstanding (57 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
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House Kailua
$167 per night
House ∙ 2 guests ∙ 1 bedroom
Beautiful Vacation Home in Kailua with Botanical Garden + Beautiful Views
4.9
Outstanding (111 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
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House Kailua
$479 per night
House ∙ 6 guests ∙ 3 bedrooms
Private House in Kailua with Pool & Yard + Next to Beach
5.0
Outstanding (130 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Kailua rental with full kitchen.

House Kailua
$760 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Kuliouou - Kalani Iki with Ample Parking
4.9
Outstanding (90 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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House Kailua
$937 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Kailua with Botanical Garden + Ocean Views
5.0
Outstanding (82 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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House Kailua
$492 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Kailua with Yard & Grill
5.0
Outstanding (35 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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Popular Rental Amenities in Kailua

  • Pool (150)
  • WiFi (356)
  • Air conditioning (309)
  • Kitchen (323)
  • TV (334)
  • Parking (27)
  • Balcony/patio (14)
  • Washing machine (311)
  • Grill (246)
  • Microwave (333)
  • No smoking (292)
  • Pet-friendly (23)

Filters are conveniently available to help you find a beautiful property in Kailua. Kailua is the perfect spot to look for an accommodation if you want a rental with a pool or you need internet access during your vacation, as the most frequently offered amenities are "Pool" and "Internet." You can even find properties if you want a rental providing a crib (46 rentals include "Crib" in Kailua) or if you need a crib for your baby (47 rentals in Kailua include "Detached").

The Weather in Kailua

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25°
16°
9 days 9
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25°
17°
11 days 11
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25°
17°
11 days 11
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26°
17°
9 days 9
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26°
18°
16 days 16
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27°
19°
12 days 12
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27°
20°
14 days 14
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28°
20°
11 days 11
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28°
20°
13 days 13
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27°
19°
11 days 11
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26°
18°
6 days 6
max.
Min.
26°
17°
6 days 6
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Kailua. During August, maximum temperatures go up to more than 28° No heat wave is expected in January, where minimum average temperatures usally hit a 16° low. Bring your umbrella in May, the rainiest month of the year!

7-Day Weather Forecast in Kailua

Sun., 24 Sep.
26°
25°

15%

2 h

21 km/h

Mon., 25 Sep.
26°
25°

15%

3 h

20 km/h

Tue., 26 Sep.
26°
25°

15%

5 h

23 km/h

Wed., 27 Sep.
26°
25°

15%

5 h

29 km/h

Thu., 28 Sep.
26°
25°

15%

4 h

30 km/h

Fri., 29 Sep.
26°
25°

15%

1 h

25 km/h

Sat., 30 Sep.
27°
25°

15%

4 h

14 km/h

Where to find the best food in Kailua?

Where to Eat in Kailua

If you're visiting Kailua on a Thursday, you can't pass up a trip to the Kailua Farmers Market. Try some local dragon fruit, or sample foods of all ethnicities including Hawaiian, Japanese, and Thai. When it comes to dining out, Cinnamon's Restaurant is the place to go for breakfast. Otherwise, try Buzz's Lanikai for excellent surf 'n' turf (and plenty of tropical cocktails).

What is the weather like in Kailua?

Climate in Kailua

Temperatures are pleasant year-round in Kailua, with an average daily temperature of 80.8°F. Be sure to pack lots of sunscreen, and stay hydrated! Kailua gets its share of rainfall, so keep in mind that hiking trails can become slippery when wet. The Olomana Three Peaks Trail can become particularly unpredictable when wet. Otherwise, enjoy hot temperatures and plenty of sun.

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 350 homes
💳 Possible discounts up to 34%
🌙 Nightly prices starting at $163
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 22 homes
🏊 Vacation rentals with pools 144 homes

Frequently Asked Questions

What is the typical price of a vacation home in Kailua?

The nightly price for accommodation in Kailua starts at $163.

What is the typical availability of House rental in Kailua?

February has the highest availability of House rental in Kailua, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities in Kailua?

When looking to book a vacation home in Kailua, the most requested amenities include Pool, Internet, and Air conditioning.

How many House rental and Apartment rental can I find in Kailua?

Kailua has 350 House rental and Apartment rental available to book.

Are there pet-friendly vacation rentals in Kailua?

If you're travelling with a dog, over 6% of vacation rentals in Kailua are pet-friendly.

What's the best month to visit Kailua?

If you're looking for balmy weather, August and September are typically the hottest months in Kailua with temperatures around 28 °C. January and February in Kailua are the coldest, with 16 °C on average.

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