Hawaii holiday rentals

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Booking Insights
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Latest Hawaii holiday rental deals

MOST POPULARHonolulu
Holiday homes from $96
Kailua-Kona
Holiday homes from $155

Best Hawaii holiday rentals

HBR Family Lockoff 1206, Mountain View, Close to the Pool Add'l Resort Fees - Princeville - Living room
HBR Family Lockoff 1206, Mountain View, Close to the Pool Add'l Resort Fees
Princeville, Kaua'i, HI, United States
8.8Very Good(66)
Condo
$515+
Check availability
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath - Hana - Beach
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana, Maui, HI, United States
9.6Wonderful(66)
Cottage
Free Wi-Fi
$802+
Check availability
1 Bedroom Condo, Kitchen, Lanai, Princeville - Princeville - Beach
1 Bedroom Condo, Kitchen, Lanai, Princeville
Princeville, Kaua'i, HI, United States
9.4Wonderful(22)
Condo
Free Wi-Fi
Pool
$462+
Check availability
Hana Kai Maui - Oceanfront 'kaahumanu' Upper Corner 100 Off Water - Hana - Living room
Hana Kai Maui - Oceanfront 'kaahumanu' Upper Corner 100 Off Water
Hana, Maui, HI, United States
9.9Wonderful(42)
Condo
Parking
Free Wi-Fi
$1,719+
Check availability
Corner studio with fast WiFi, expansive mountain views, pool, & grills - Princeville - Building
Corner studio with fast WiFi, expansive mountain views, pool, & grills
Princeville, Kaua'i, HI, United States
8.0Very Good(10)
House
$508+
Check availability
Alii Kai Ii 8H - Princeville - Balcony
Alii Kai Ii 8H
Princeville, Kaua'i, HI, United States
8.6Very Good(11)
Apartment
Parking
Free Wi-Fi
Pool
$674+
Check availability
Secluded cottage on Tropical flower farm - Hana - Patio
Secluded cottage on Tropical flower farm
Hana, Maui, HI, United States
9.7Wonderful(127)
Cottage
$726+
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Emmalani Court 411 - Princeville - Beach
Emmalani Court 411
Princeville, Kaua'i, HI, United States
9.4Wonderful(14)
Apartment
Parking
Free Wi-Fi
Pool
$703+
Check availability
Hbr Studio Lockoff 1557, King Bed And Queen Sleeper, Ac Add'l Resort Fees - Princeville - Balcony
Hbr Studio Lockoff 1557, King Bed And Queen Sleeper, Ac Add'l Resort Fees
Princeville, Kaua'i, HI, United States
8.5Very Good(37)
Condo
$534+
Check availability
Authentic Hawaiian Beach House On Hana Bay. 5-Minute Walk To Beaches And Town. - Hana - Living room
Authentic Hawaiian Beach House On Hana Bay. 5-Minute Walk To Beaches And Town.
Hana, Maui, HI, United States
9.9Wonderful(21)
Cottage
Free Wi-Fi
$1,152+
Check availability
Sealodge D7 - Princeville - Balcony
Sealodge D7
Princeville, Kaua'i, HI, United States
8.7Very Good(16)
Apartment
Parking
Free Wi-Fi
Pool
$720+
Check availability
Princeville - Cliffs 2-109 Spacious, Affordable 1br/2ba Condo - Princeville - Pool
Princeville - Cliffs 2-109 Spacious, Affordable 1br/2ba Condo
Princeville, Kaua'i, HI, United States
9.1Wonderful(42)
Condo
$536+
Check availability
Oceanview Condo in Hana-Let the ocean lull you to sleep - Hana - Bedroom
Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana, Maui, HI, United States
9.2Wonderful(77)
Apartment
Free Wi-Fi
$774+
Check availability
Puamana 16b - Princeville - Bedroom
Puamana 16b
Princeville, Kaua'i, HI, United States
9.1Wonderful(36)
Apartment
Parking
Free Wi-Fi
Pool
$877+
Check availability
Camp Alealea 2 home - Hanalei - Bedroom
Camp Alealea 2 home
Hanalei, Kaua'i, HI, United States
House
Parking
Free Wi-Fi
$4,596+
Check availability
Hanalei Bay Resort 2302 - Princeville
Hanalei Bay Resort 2302
Princeville, Kaua'i, HI, United States
4.8Mediocre(5)
House
Pool
$555+
Check availability
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 89 days before your stay begins to get the best price for your Hawaii vacation rental.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
July
$777
$789
Cheapest month to stay with an average 10% drop in price.
Most expensive month to stay with an average 44% 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 August and March.
  • The cheapest night for renting a holiday home in Hawaii is Friday. 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 4 days.
  • The cheapest Hawaii holiday rental found on KAYAK in the last 2 weeks was $301, while the most expensive was $336.
  • Pool, beachfront, air-conditioned, and kitchen/kitchenette 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 Honolulu, with around 2,544 properties and an average price of $301. The most popular holiday rentals in Hawaii among KAYAK users are Castle Waikiki Shore Beachfront Condominiums, Luana Waikiki Park Views - no resort fees, and Lovely Hawaiian Monarch Studio.

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 (54% of total searches to Hawaii). The next most popular destinations are Kailua-Kona (21%) and Kahului (13%). Searches for holida rentals in Hilo (5%), Lahaina (3%) and Lihue (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 $309. 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 $239 per night. 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 $2,109.

  • 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 $9,040.

  • 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, cabins, campgrounds, caravans, homestays, lodges, luxury tents, motorhomes, campsites, aparthotels, bungalows, hotels, resorts, agritourism and caravan parks.

  • 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 Castle Kona Bali Kai and Stay Condominiums Waikiki.

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.

Everything you need to know for your stay in Hawaii

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