Hawaii holiday rentals

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Recommended by KAYAK

Best Hawaii holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$13 - $404$404 - $797$797 - $1,190$1,190 - $1,580$1,580+ per night

Property type

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Most recommended holiday rentals in Hawaii

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Paki Maui 316 - Lahaina
Paki Maui 316
Lahaina, Maui, HI, United States
9.2Wonderful(3)
Free Wi-Fi
Pool
$401+
Check availability
Kaleialoha 402 - Lahaina
Kaleialoha 402
Lahaina, Maui, HI, United States
8.2Very Good(5)
Parking
Free Wi-Fi
Pool
$405+
Check availability
Kahana Beach Vacation Club - Lahaina - Pool
Kahana Beach Vacation Club
Lahaina, Maui, HI, United States
8.1Very Good(333)
Parking
Free Wi-Fi
Pool
$431+
Check availability
Maui Kamaole H-101 - Wailea
Maui Kamaole H-101
Wailea, Maui, HI, United States
8.5Very Good(2)
Parking
Free Wi-Fi
Pool
$458+
Check availability
Hale Ono Loa 203 - Lahaina
Hale Ono Loa 203
Lahaina, Maui, HI, United States
8.7Very Good(2)
Free Wi-Fi
Pool
$465+
Check availability
Maui Banyan H-210 - Wailea - Beach
Maui Banyan H-210
Wailea, Maui, HI, United States
7.9Good(10)
Parking
Free Wi-Fi
Pool
$483+
Check availability
Kuleana Resort 313 - Lahaina
Kuleana Resort 313
Lahaina, Maui, HI, United States
9.4Wonderful(5)
Free Wi-Fi
Pool
$485+
Check availability
Maui Vista 3111 - Mch - Wailea - Pool
Maui Vista 3111 - Mch
Wailea, Maui, HI, United States
7.8Good(11)
Free Wi-Fi
Pool
$510+
Check availability
Castle Kaha Lani Resort - Lihue - Living room
Castle Kaha Lani Resort
Lihue, Kaua'i, HI, United States
10Wonderful(5)
Free Wi-Fi
Pool
$510+
Check availability
Lahaina Wonderful Condos - Paki Maui - Lahaina
Lahaina Wonderful Condos - Paki Maui
Lahaina, Maui, HI, United States
8.3Very Good(50)
Parking
Free Wi-Fi
Pool
$547+
Check availability
Kihei Akahi A104 - Wailea
Kihei Akahi A104
Wailea, Maui, HI, United States
9.0Wonderful(17)
Free Wi-Fi
Pool
$591+
Check availability
Wailea Ekolu Village 1406 - Wailea
Wailea Ekolu Village 1406
Wailea, Maui, HI, United States
9.5Wonderful(22)
Parking
Free Wi-Fi
Pool
Spa
$658+
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Castle At Makahuena At Poipu - Poipu - Living room
Castle At Makahuena At Poipu
Poipu, Kaua'i, HI, United States
6.0Okay(96)
Free Wi-Fi
Pool
$759+
Check availability
Mana Kai 311A - Wailea
Mana Kai 311A
Wailea, Maui, HI, United States
10Wonderful(1)
Free Wi-Fi
Pool
$800+
Check availability
Kbm Resorts Free Car The Whaler Ocean View Studio With Stunning Sunset Wh1-1218 - Lahaina - Beach
Kbm Resorts Free Car The Whaler Ocean View Studio With Stunning Sunset Wh1-1218
Lahaina, Maui, HI, United States
9.0Wonderful(9)
Parking
Free Wi-Fi
Pool
Pet friendly
$923+
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Koa Resort 4I - Wailea
Koa Resort 4I
Wailea, Maui, HI, United States
9.5Wonderful(4)
Parking
Free Wi-Fi
Pool
$982+
Check availability
Useful Info

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 89 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)

February
June
$612
$721
Cheapest month to stay with an average 8% drop in price.
Most expensive month to stay with an average 81% 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 October and November.
  • The cheapest night for renting a holiday home in Hawaii is Saturday. In contrast, the most expensive is Tuesday.
  • Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Hawaii for 4 days.
  • The cheapest Hawaii holiday rental found on KAYAK in the last 2 weeks was $275, while the most expensive was $315.
  • Beachfront, air-conditioned, kitchen/kitchenette, and pool are the most popular holiday rental property amenities in Hawaii
  • Holiday rentals in Hawaii are around 18% 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 Honolulu (67% of total searches to Hawaii). The next most popular destinations are Kailua-Kona (17%) and Kahului (6%). Searches for holida rentals in Hilo (3%), Lihue (3%) and Kapolei (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 $223. 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 $223 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, homestays, studios, villas, agritourism, cabins, campgrounds, caravans, lodges, luxury tents, motorhomes, bungalows, 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 1% allowing you to bring your pet along with you.

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(289)
Free Wi-Fi
$468+
Check availability

Everything you need to know for your stay in Hawaii

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