Hawaii holiday rentals

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Best Hawaii holiday rentals

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£24 - £191£191 - £358£358 - £525£525 - £692£692+ per night

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Most recommended holiday rentals in Hawaii

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Downtown Kailua-Kona Escape Steps to Ocean! - Kailua-Kona - Pool
Downtown Kailua-Kona Escape Steps to Ocean!
Kailua-Kona, The Big Island, HI, United States
7.0Good(40)
Free Wi-Fi
Pool
Air conditioning
£160+
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Kona Plaza#218 - Kailua-Kona - Building
Kona Plaza#218
Kailua-Kona, The Big Island, HI, United States
8.8Very Good(25)
Parking
Free Wi-Fi
Pool
Air conditioning
£163+
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Ideal Location! Beautiful Ocean View; Escape to Paradise. Last Minute Specials! - Kahaluu-Keauhou - Building
Ideal Location! Beautiful Ocean View; Escape to Paradise. Last Minute Specials!
Kahaluu-Keauhou, The Big Island, HI, United States
9.3Wonderful(13)
Free Wi-Fi
£163+
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Kona Isle C35 - Kailua-Kona - Living room
Kona Isle C35
Kailua-Kona, The Big Island, HI, United States
8.8Very Good(15)
Parking
Free Wi-Fi
Pool
Air conditioning
£173+
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Lovely Ground Floor Unit! - Kailua-Kona - Beach
Lovely Ground Floor Unit!
Kailua-Kona, The Big Island, HI, United States
9.7Wonderful(61)
Free Wi-Fi
Air conditioning
£173+
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Gardens At West Maui - Kapalua - Bedroom
Gardens At West Maui
Kapalua, Maui, HI, United States
8.4Very Good(145)
Parking
Free Wi-Fi
Pool
Air conditioning
£185+
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Kona Shores 221 Beautiful Top Floor Corner Condo w/AC! - Kailua-Kona - Pool
Kona Shores 221 Beautiful Top Floor Corner Condo w/AC!
Kailua-Kona, The Big Island, HI, United States
9.0Wonderful(32)
Air conditioning
£188+
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Unit 5 Maui Ohana Modern Studio - Wailuku - Beach
Unit 5 Maui Ohana Modern Studio
Wailuku, Maui, HI, United States
9.2Wonderful(10)
Parking
Free Wi-Fi
Air conditioning
£194+
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Unit 7 Maui Ohana Modern Studio - Wailuku - Beach
Unit 7 Maui Ohana Modern Studio
Wailuku, Maui, HI, United States
9.0Wonderful(18)
Parking
Free Wi-Fi
Air conditioning
£195+
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Casa De Emdeko 129 The Best Vacation Experience In Kona Hawaii! - Kailua-Kona - Pool
Casa De Emdeko 129 The Best Vacation Experience In Kona Hawaii!
Kailua-Kona, The Big Island, HI, United States
10Wonderful(19)
Free Wi-Fi
Air conditioning
£209+
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Unit 19 Maui Ohana Modern Studio - Wailuku
Unit 19 Maui Ohana Modern Studio
Wailuku, Maui, HI, United States
8.7Very Good(13)
Parking
Free Wi-Fi
Air conditioning
£233+
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Palms at Wailea 1302! Top Floor Condo with Amazing Garden and Ocean Views! - Kīhei - Living room
Palms at Wailea 1302! Top Floor Condo with Amazing Garden and Ocean Views!
Kīhei, Maui, HI, United States
7.4Good(20)
Free Wi-Fi
Air conditioning
£375+
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Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub - Kīhei - Dining room
Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub
Kīhei, Maui, HI, United States
9.5Wonderful(25)
Free Wi-Fi
£425+
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Kaanapali Shores - 259 - Kaanapali - Living room
Kaanapali Shores - 259
Kaanapali, Maui, HI, United States
9.7Wonderful(34)
Free Wi-Fi
Pool
Air conditioning
£448+
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2102 Fairways at Mauna Lani - Waimea (Big Island)
2102 Fairways at Mauna Lani
Waimea (Big Island), The Big Island, HI, United States
9.7Wonderful(24)
Parking
Free Wi-Fi
Pool
Air conditioning
£475+
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Outrigger Honua Kai Resort & Spa - Select Your Unit - Lahaina
Outrigger Honua Kai Resort & Spa - Select Your Unit
Lahaina, Maui, HI, United States
8.9Very Good(17)
Parking
Free Wi-Fi
Pool
Air conditioning
£559+
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Booking Insights

KAYAK’s insights for holiday rentals in Hawaii

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Hawaii with confidence.

How early should you book a vacation rental in Hawaii?

Book at least 20 days before your stay begins to get the best price for your Hawaii vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
February
£332
£307
Cheapest month to stay with an average 21% drop in price.
Most expensive month to stay with an average 29% 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 February and April.
  • The cheapest night for renting a holiday home in Hawaii is Tuesday. In contrast, the most expensive is Monday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Hawaii for 12 days.
  • Pool, air-conditioned, kitchen/kitchenette, and beachfront are the most popular holiday rental property amenities in Hawaii
  • Holiday rentals in Hawaii are around 10% cheaper than hotels on average. Search here to compare prices for all accommodation types in Hawaii.

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 Kahului (40% of total searches to Hawaii). The next most popular destinations are Honolulu (30%) and Kailua-Kona (9%). Searches for holida rentals in Kapalua (3%), Princeville (2%) and Lihue (2%) 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 £122. Search here for similar prices

  • How much is a holiday rental in Hawaii for this weekend?

    In the last 72 hours, users have found Hawaii holiday rentals for this weekend for as little as £80 per night. Search here for similar prices

  • 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, studios, villas, caravans, homestays, luxury tents, cabins, campgrounds, lodges, motorhomes, campsites, bungalows, hotels, resorts, aparthotels, agritourism, 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 Fairway Villas Waikoloa By Outrigger and Wailea Ekahi Village - CoralTree Residence Collection.

  • What are the most popular Hawaii holiday rentals for a large group?

    If you’re a large group then you’ll need plenty of space. The highest rated holiday home that can sleep 6 people or more by KAYAK users is Lae Nani Resort Kauai By Outrigger.

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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Popular topics

Holiday rentals by topic

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Stay Condominiums Waikiki - Honolulu - Bedroom
Stay Condominiums Waikiki
Waikiki
6.2Okay(288)
Free Wi-Fi
Air conditioning
£228+
Check availability

Everything you need to know for your stay in Hawaii

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