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Kailua Vacation Rentals

Find 362 available offers from 16 partners
Kailua
Anytime
Guests
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+

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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Vacation rentals with Wi-Fi

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

Cottage  Kailua
Oct 19 - Oct 26
$755 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage in Kailua with Beautiful Pool

4.8
Outstanding (138 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
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Apartment  Kailua
Oct 19 - Oct 26
$553 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment in Kailua with Beautiful Pool

4.8
Outstanding (143 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
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House  Kailua
Nov 16 - Nov 23
$1,113 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Kailua with Botanical Garden

4.9
Outstanding (70 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.

Apartment  Kailua
Oct 19 - Oct 26
$470 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Kailua with Secret Garden

4.9
Outstanding (108 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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Cottage  Kailua
Oct 19 - Oct 26
$858 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in Kailua with Patio + Ocean View

4.8
Outstanding (88 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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House  Kailua
Oct 19 - Oct 26
$935 per night
House ∙ 5 guests ∙ 2 bedrooms

House in Kailua with Beautiful Pool

4.8
Outstanding (212 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
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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
Jun 19 - Jun 26
$1,006 per night
House ∙ 2 guests ∙ 1 bedroom

House in Kailua with Pool, Grill & Patio

4.7
Excellent (168 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Apartment  Kailua
Apr 16 - Apr 23
$728 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Pleasant Rental Apartment in Kailua with Grill, Yard & Pool + Mountain Views

4.7
Excellent (152 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
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House  Kailua
May 25 - Jun 1
$411 per night
House ∙ 2 guests ∙ 1 bedroom

Nice House in Kailua

Kailua, Honolulu County, Hawaii, United States
Air conditioning
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Best Vacation Home Deals in Kailua

Save up to 34%

House Kailua
Apr 6 - Apr 13
-34%
$633
$417 per night
House ∙ 4 guests ∙ 2 bedrooms

Nice House in Kailua

Kailua, Honolulu County, Hawaii, United States
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House Kailua
Nov 16 - Nov 23
-4%
$742
$715 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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Resort Kailua
Nov 9 - Nov 16
-24%
$405
$308 per night
Resort ∙ 127 guests ∙ 2 bedrooms

Beautiful Resort in Kahaluu with Outdoor Pool

4.2
Very good
Kailua, Honolulu County, Hawaii, United States
Free cancellation
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Search and compare the 362 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 $157 per night

House Kailua
May 3 - May 10
$1,468 per night
House ∙ 12 guests ∙ 7 bedrooms

House in Kaneohe

Kailua, Honolulu County, Hawaii, United States
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Tent Kailua
Jun 1 - Jun 8
$203 per night
Tent ∙ 2 guests ∙ 1 bedroom

Tent in Kahaluu

Kailua, Honolulu County, Hawaii, United States
Free cancellation
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House Kailua
Nov 16 - Nov 23
$666 per night
House ∙ 4 guests ∙ 1 bedroom

Vacation Home in Kailua with Botanical Garden

4.7
Excellent (87 ratings)
Kailua, Honolulu County, Hawaii, United States
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Apartment Kailua
Oct 19 - Oct 26
$626 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Kailua with Botanical Garden + Panoramic View

5.0
Outstanding (251 ratings)
Kailua, Honolulu County, Hawaii, United States
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Bed and breakfast Kailua
Sept 21 - Sept 28
$465 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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House Kailua
Oct 5 - Oct 12
$595 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Mānoa + Panaramic Views

4.7
Excellent (48 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
Apr 16 - Apr 23
$2,190 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Waimanalo Beach with Patio, Yard & Grill + Beautiful Views

4.9
Outstanding (122 ratings)
Kailua, Honolulu County, Hawaii, United States
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House Kailua
May 11 - May 18
$1,046 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
Free cancellation
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House Kailua
Jun 29 - Jul 6
$13,729 per night
House ∙ 12 guests ∙ 6 bedrooms

Wonderful Vacation Home in Makiki - Lower Punchbowl - Tantalus with Pool & Jacuzzi

Kailua, Honolulu County, Hawaii, United States
Free cancellation
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Budget-friendly Rentals in Kailua

Find Fantastic yet Inexpensive Rentals

House Kailua
$243 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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Villa Kailua
$255 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
Oct 5 - Oct 12
$766 per night
House ∙ 4 guests ∙ 2 bedrooms

Lovely Vacation Home in Mānoa + Mountain Views

4.9
Outstanding (45 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
$591 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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House Kailua
$1,355 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
$853 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Kailua with Grill & Patio + Unobstructed Views

4.9
Outstanding (27 ratings)
Kailua, Honolulu County, Hawaii, United States
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Popular Rental Amenities in Kailua

  • Pool (158)
  • WiFi (358)
  • Air conditioning (310)
  • Kitchen (330)
  • TV (330)
  • Parking (29)
  • Balcony/patio (188)
  • Washing machine (320)
  • Grill (232)
  • Microwave (313)
  • No smoking (348)
  • 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 $2,282 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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12 days 12
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13 days 13
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6 days 6
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6 days 6
Jan.
Feb.
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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

Fri., 29 Mar.
24°
23°

15%

1 h

29 km/h

Sat., 30 Mar.
23°
23°

15%

0 h

26 km/h

Sun., 31 Mar.
24°
23°

10%

6 h

19 km/h

Mon., 1 Apr.
24°
23°

15%

3 h

26 km/h

Tue., 2 Apr.
23°
23°

15%

0 h

27 km/h

Wed., 3 Apr.
24°
23°

15%

0 h

28 km/h

Thu., 4 Apr.
24°
23°

15%

0 h

38 km/h

Accommodations for your vacation in Kailua

In Kailua, many of the vacation accommodations are house rental, which represent 61.82% of its listed properties. Additionally, they have an average size of 219 m² as well as a median price of $1,602 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 $366 per night for an area of 62 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 362 rentals
💳 Possible discounts up to 34%
🌙 Nightly prices starting at $157
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 22 homes
🏊 Vacation rentals with pools 158 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Kailua?

August 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 22 pet-friendly vacation rentals in Kailua, with an average nightly price of $819.

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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