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Kailua Vacation Rentals

Find 347 available offers from 15 partners
Kailua
Anytime
Guests
Kailua
Anytime
Guests

Popular Filters to find the Perfect Rental in Kailua

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

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.

Show all 362 properties

Vacation rentals and apartments with air conditioning

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

House  Kailua
May 11 - May 18
-7%
$751
$696 per night
House ∙ 9 guests ∙ 2 bedrooms

Vacation Home in Kailua with Botanical Garden + Mountain Views + Close to Beach

4.4
Very good (58 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House  Kailua
Jul 13 - Jul 20
$414 per night
House ∙ 2 guests ∙ 1 bedroom

Nice House in Kailua

Kailua, Honolulu County, Hawaii, United States
Free cancellation
Air conditioning
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Boat  Kailua
May 25 - Jun 1
$227 per night
Boat ∙ 4 guests ∙ 1 bedroom

Boat in Kailua

Kailua, Honolulu County, Hawaii, United States
Free cancellation
Air conditioning
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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.

Resort  Kailua
Dec 14 - Dec 21
$346 per night
Resort ∙ 127 guests ∙ 2 bedrooms

Beautiful Resort in Kahaluu with Outdoor Pool

4.2
Very good (1 rating)
Kailua, Honolulu County, Hawaii, United States
Free cancellation
Kitchen
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House  Kailua
Dec 12 - Dec 19
$779 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home in Mānoa + Mountain Views

4.9
Outstanding (47 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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House  Kailua
May 18 - May 25
-25%
$1,408
$1,055 per night
House ∙ 4 guests ∙ 3 bedrooms

Vacation Home in Kaneohe with Yard, Pool & Patio + Magnificent Views

4.0
Very good (2 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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Apartments with a balcony or patio

Looking for a home with a balcony? Check out these vacation homes in Kailua with their own private patios and balconies.

House  Kailua
$968 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Kailua with Botanical Garden

4.9
Outstanding (68 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
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House  Kailua
$802 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Makiki - Lower Punchbowl - Tantalus with Yard, Sauna & Grill

5.0
Outstanding (14 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
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House  Kailua
$394 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Kailua with Outdoor Garden

5.0
Outstanding (34 ratings)
Kailua, Honolulu County, Hawaii, United States
Balcony/Patio
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Best Vacation Home Deals in Kailua

Save up to 43%

House Kailua
Jun 5 - Jun 12
-43%
$1,972
$1,120 per night
House ∙ 4 guests ∙ 1 bedroom

House in Kailua with Tropical Garden

4.8
Outstanding (46 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 9 - Nov 16
-37%
$6,068
$3,832 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kailua with Grill, Patio & Yard

4.9
Outstanding (43 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 9 - Nov 16
-4%
$752
$725 per night
House ∙ 5 guests ∙ 2 bedrooms

Pleasant Vacation Home in Kuliouou - Kalani Iki with Yard, Grill & Patio + Ocean Views

4.9
Outstanding (134 ratings)
Kailua, Honolulu County, Hawaii, United States
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Search and compare the 347 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.

Recommended Vacation Rentals in Kailua

Find your perfect vacation rental in Kailua: from $170 per night

Tent Kailua
May 3 - May 10
$204 per night
Tent ∙ 2 guests ∙ 1 bedroom

Tent in Kahaluu

Kailua, Honolulu County, Hawaii, United States
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House Kailua
$594 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Kailua with Private Pool + Panoramic Views

4.5
Excellent (21 ratings)
Kailua, Honolulu County, Hawaii, United States
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Bed and breakfast Kailua
Sept 16 - Sept 23
$469 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

B&B in Kailua with Outdoor Garden

4.7
Excellent (3 ratings)
Kailua, Honolulu County, Hawaii, United States
Free cancellation
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Villa Kailua
$253 per night
Villa ∙ 14 guests ∙ 6 bedrooms

Villa in Kailua with Weekly Pool + Ocean Views

5.0
Outstanding (4 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$247 per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation Home in Kailua with Yard, Patio & Grill

5.0
Outstanding (92 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$1,346 per night
House ∙ 16 guests ∙ 8 bedrooms

Gorgeous House in Kailua with Patio, Pool & Yard

4.8
Outstanding (83 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$929 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in Kailua with Yard, Patio & Grill + Ocean Views

4.6
Excellent (142 ratings)
Kailua, Honolulu County, Hawaii, United States
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Bed and breakfast Kailua
$482 per night
Bed and breakfast ∙ 3 guests ∙ 2 bedrooms

Bed & Breakfast in Kailua with Botanical Garden

4.7
Excellent (64 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
$393 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental Apartment in Kailua + Next to Beach

4.8
Outstanding (41 ratings)
Kailua, Honolulu County, Hawaii, United States
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Budget-friendly Rentals in Kailua

Find Fantastic yet Inexpensive Rentals

House Kailua
$1,057 per night
House ∙ 8 guests ∙ 4 bedrooms

Nice House in Kailua with Pool, Yard & Grill

4.9
Outstanding (139 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$1,452 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Kailua with Pool, Grill & Patio

5.0
Outstanding (122 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
$612 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Kailua with Botanical Garden + Beach Nearby

5.0
Outstanding (69 ratings)
Kailua, Honolulu County, Hawaii, United States
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Top-Rated Offers and Accommodations in Kailua

Book Vacation Rentals with the Highest User Rating

House Kailua
$489 per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation Home in Kailua with Grill & Patio

4.7
Excellent (97 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$2,944 per night
House ∙ 14 guests ∙ 8 bedrooms

House in Kailua with Pool, Patio & Yard + Close to Beach

4.7
Excellent (97 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
$1,438 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Kailua with Grill, Yard & Patio

5.0
Outstanding (43 ratings)
Kailua, Honolulu County, Hawaii, United States
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Popular Rental Amenities in Kailua

  • Pool (156)
  • WiFi (356)
  • Air conditioning (314)
  • Kitchen (330)
  • TV (332)
  • Parking (28)
  • Balcony/patio (193)
  • Washing machine (317)
  • Grill (235)
  • Microwave (310)
  • No smoking (345)
  • Pet-friendly (22)

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 $2,286 per night. If you would ideally like to be close to the water, two-thirds of the vacation homes providing a pool are located within 2 kilometres of the waterfront.

The Weather in Kailua

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16°
9 days 9
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11 days 11
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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°
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13 days 13
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27°
19°
11 days 11
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26°
18°
6 days 6
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26°
17°
6 days 6
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Kailua climate diagram. 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. The month of November has nice weather with only 6 rainy days.

7-Day Weather Forecast in Kailua

Tue., 23 Apr.
24°
23°

15%

2 h

30 km/h

Wed., 24 Apr.
24°
23°

15%

1 h

31 km/h

Thu., 25 Apr.
24°
23°

15%

2 h

33 km/h

Fri., 26 Apr.
24°
23°

10%

3 h

29 km/h

Sat., 27 Apr.
23°
23°

15%

1 h

29 km/h

Sun., 28 Apr.
24°
24°

15%

2 h

19 km/h

Mon., 29 Apr.
24°
23°

15%

0 h

26 km/h

Accommodations for your vacation in Kailua

In Kailua, many of the vacation accommodations are house rental, which represent 61.9% of its listed properties. Additionally, they have an average size of 220 m² as well as a median price of $1,613 a night. Moreover, if you are going in a group of 8, vacation rentals are a great property type in Kailua, as they usually accommodate this exact group size. If you are searching for another type of accommodation, you can find many other options, such as apartment rental, which are another typical type of property in Kailua. Our data shows that the median price of vacation homes is $369 per night for an area of 63 m².
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 347 rentals
💳 Possible discounts up to 43%
🌙 Nightly prices starting at $160
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 22 homes
🏊 Vacation rentals with pools 151 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Kailua?

December 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 21 pet-friendly vacation rentals in Kailua, with an average nightly price of $855.

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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