Hawaii holiday rentals

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Best Hawaii holiday rentals

Most recommended holiday rentals in Hawaii

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Kona Mansions#302 - Kailua-Kona - Living room
Kona Mansions#302
Kailua-Kona, The Big Island, HI, United States
9.0Wonderful(37)
Parking
Free Wi-Fi
Pool
$442+
Check availability
Kona Isle B22 - Kailua-Kona - Pool
Kona Isle B22
Kailua-Kona, The Big Island, HI, United States
8.6Very Good(18)
Parking
Free Wi-Fi
Pool
$332+
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Casa De Emdeko 105 - Kailua-Kona - Pool
Casa De Emdeko 105
Kailua-Kona, The Big Island, HI, United States
9.3Wonderful(22)
Parking
Free Wi-Fi
Pool
$482+
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Big Island Kona Islander By Coldwell Ban - Kailua-Kona - Kitchen
Big Island Kona Islander By Coldwell Ban
Kailua-Kona, The Big Island, HI, United States
9.2Wonderful(18)
Pool
$357+
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Oceanfront Condo & Walking Distance to Beach and Town- Hale Kona Kai 207 by Casago Kona - Kailua-Kona - Balcony
Oceanfront Condo & Walking Distance to Beach and Town- Hale Kona Kai 207 by Casago Kona
Kailua-Kona, The Big Island, HI, United States
8.4Very Good(18)
Parking
Free Wi-Fi
$588+
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Breezy Condo with Screened Lanai in Kailua-Kona! - Kailua-Kona - Pool
Breezy Condo with Screened Lanai in Kailua-Kona!
Kailua-Kona, The Big Island, HI, United States
8.0Very Good(10)
Free Wi-Fi
Pool
$405+
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Beach Condo, Lovely, Clean, Comfy Heart of Kona! Poolside, Hot Tub, Beach Stuff - Kailua-Kona - Pool
Beach Condo, Lovely, Clean, Comfy Heart of Kona! Poolside, Hot Tub, Beach Stuff
Kailua-Kona, The Big Island, HI, United States
Free Wi-Fi
Spa
$409+
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Keauhou Resort #111 - Kailua-Kona - Balcony
Keauhou Resort #111
Kailua-Kona, The Big Island, HI, United States
9.5Wonderful(2)
Free Wi-Fi
Pool
$387+
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Casa de Emdeko 306 - Kailua-Kona - Beach
Casa de Emdeko 306
Kailua-Kona, The Big Island, HI, United States
8.7Very Good(13)
Parking
Free Wi-Fi
Pool
$511+
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Kona Paradise Ocean condo w/pool Lokahi at Alii Villas - Kailua-Kona - Balcony
Kona Paradise Ocean condo w/pool Lokahi at Alii Villas
Kailua-Kona, The Big Island, HI, United States
8.3Very Good(21)
$477+
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Kona @ Alii Villas Oceanfront Resort Condo - Kailua-Kona - Pool
Kona @ Alii Villas Oceanfront Resort Condo
Kailua-Kona, The Big Island, HI, United States
10Wonderful(1)
Free Wi-Fi
$265+
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Big Island Kanaloa at Kona by Coldwell Banker Island Vacations - Kailua-Kona - Beach
Big Island Kanaloa at Kona by Coldwell Banker Island Vacations
Kailua-Kona, The Big Island, HI, United States
8.9Very Good(14)
Pool
Spa
$767+
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Carson's Kaloko Mountain Cabin - Kailua-Kona - Bedroom
Carson's Kaloko Mountain Cabin
Kailua-Kona, The Big Island, HI, United States
Free Wi-Fi
Spa
$427+
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Alii Villas 218 condo - Kailua-Kona - Balcony
Alii Villas 218 condo
Kailua-Kona, The Big Island, HI, United States
9.0Wonderful(2)
Free Wi-Fi
Pool
$217+
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Royal Sea Cliff 705! Panoramic Ocean Views! - Kailua-Kona - Balcony
Royal Sea Cliff 705! Panoramic Ocean Views!
Kailua-Kona, The Big Island, HI, United States
Pool
Spa
$608+
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Castle Waikiki Shore - Honolulu - Beach
Castle Waikiki Shore
Waikiki
8.5Very Good(1116)
Free Wi-Fi
$485+
Check availability
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$13 - $1,628$1,628 - $3,243$3,243 - $4,858$4,858 - $6,472$6,472+ per night

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Good to know

Low season

September

High season

January

Average price (weeknight)

$851

Average price (weekend night)

$838
Cheapest month to stay with an average 7% drop in price.
Most expensive month to stay with an average 27% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Hawaii holiday rental

  • If you’re looking for a cheap holiday rental in Hawaii, you should consider visiting during the low season. The cheapest holiday homes in Hawaii can be found in September and January.
  • The cheapest night for renting a holiday home in Hawaii is Tuesday. In contrast, the most expensive is Wednesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Hawaii for 3 days.
  • The cheapest Hawaii holiday rental found on KAYAK in the last 2 weeks was $514, while the most expensive was $563.
  • Beachfront, kitchen/kitchenette, pool, air-conditioned, and parking are the most popular holiday rental property amenities in Hawaii
  • Holiday rentals in Hawaii are around 28% cheaper than hotels on average. Search here to compare prices for all accommodation types in Hawaii.
  • The city in Hawaii with the most affordable holiday homes is Kekaha, with around 21 properties and an average price of $315. The most popular holiday rentals in Hawaii among KAYAK users are Oceanfront Sunny Westside Tvrncu- #1094, Hale Mano Kia - Classic 3br West Side Bungalow . Steps From The Beach! Tvnc 5001, and White Sand Beaches on the Sunny Westside of Kauai..
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FAQs when booking a holiday home in Hawaii

  • What is the most popular holiday rental destination in Hawaii?

    Based on KAYAK holiday rental searches, the most popular destination is Honolulu (64% of total searches to Hawaii). The next most popular destinations are Kekaha (18%) and Kailua-Kona (9%). Searches for holida rentals in Kahului (3%), Kīhei (3%) and Poipu (3%) are also popular.

  • How much is a holiday rental in Hawaii for tonight?

    In the last 72 hours, users have found Hawaii holiday rentals for tonight for as little as $229. Search here for similar prices

  • How much is a holiday rental for a week in Hawaii?

    The average price for a weekly Hawaii holiday rental found by KAYAK users in the last 2 weeks is $2,206.

  • How much is a holiday rental for a month in Hawaii?

    The average price for a monthly Hawaii holiday rental found by KAYAK users in the last 2 weeks is $9,452.

  • What types of holiday rentals are available in Hawaii?

    There are loads of different property types that you can make your holiday home in Hawaii. You’ll find apartments, condos, cottages, houses, homestays, studios, villas, bungalows, cabins, campgrounds, lodges, luxury tents, caravans, motorhomes, agritourism, campsites, caravan parks and farm stays.

  • What are some of the most-loved holiday rentals available in Hawaii?

    There are many types of properties available for Hawaii holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Stay Condominiums Waikiki and Castle Kona Bali Kai.

  • Are there any pet-friendly holiday rentals in Hawaii?

    There are a number of dog and pet-friendly Hawaii holiday rentals, with around 2% allowing you to bring your pet along with you.

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Where to stay in Hawaii?

Our map will help you find the perfect place to stay in Hawaii by showing you the exact location of each holiday home.

What Hawaii holiday rental guests are talking about

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Holiday rentals by topic

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Stay Condominiums Waikiki - Honolulu
Stay Condominiums Waikiki
Waikiki
6.2Okay(289)
Free Wi-Fi
$260+
Check availability

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