Hawaii holiday rentals

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Booking Insights
Recommended by KAYAK

Best Hawaii holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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£24 - £460£460 - £896£896 - £1,332£1,332 - £1,768£1,768+ per night

Property Types

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Most recommended holiday rentals in Hawaii

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Bears' Place Guest House - Kailua-Kona - Balcony
Bears' Place Guest House
Kailua-Kona, The Big Island, HI, United States
8.1Very Good(156)
Parking
Free Wi-Fi
£155+
Check availability
Lahaina Wonderful Condos - Lahaina - Living room
Lahaina Wonderful Condos
Lahaina, Maui, HI, United States
8.8Very Good(60)
Parking
Free Wi-Fi
Pool
Air conditioning
£256+
Check availability
Kaanapali Maui At The Eldorado By Outrigger - Lahaina - Beach
Kaanapali Maui At The Eldorado By Outrigger
Lahaina, Maui, HI, United States
8.8Very Good(201)
Free Wi-Fi
Pool
Air conditioning
£280+
Check availability
Kbm Resorts Free Car Kapalua Golf Villa Ocean View 1-Bedroom Condo Recently Remodeled Kgv-19t1 - Kapalua - Living room
Kbm Resorts Free Car Kapalua Golf Villa Ocean View 1-Bedroom Condo Recently Remodeled Kgv-19t1
Kapalua, Maui, HI, United States
9.8Wonderful(6)
Parking
Free Wi-Fi
Pool
Air conditioning
£351+
Check availability
Plumeria Tree Hale - Golf Course View - Sleeps 4 - Kahuku - Pool
Plumeria Tree Hale - Golf Course View - Sleeps 4
Kahuku, O'ahu, HI, United States
9.5Wonderful(35)
Parking
Free Wi-Fi
Pool
Air conditioning
£355+
Check availability
Kapalua Ridge Villas By Kbm Resorts - Kapalua - Living room
Kapalua Ridge Villas By Kbm Resorts
Kapalua, Maui, HI, United States
9.0Wonderful(11)
Parking
Free Wi-Fi
Pool
Pet-friendly
£403+
Check availability
Kona Sunset House at Walua - Kailua-Kona - Balcony
Kona Sunset House at Walua
Kailua-Kona, The Big Island, HI, United States
9.6Wonderful(41)
Parking
Free Wi-Fi
£403+
Check availability
Rare 2 Bedroom & Loft Townhouse on the North Shore - Kahuku - Pool
Rare 2 Bedroom & Loft Townhouse on the North Shore
Kahuku, O'ahu, HI, United States
8.3Very Good(58)
Parking
Free Wi-Fi
Pool
Air conditioning
£409+
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Protea Condo - Kahuku
Protea Condo
Kahuku, O'ahu, HI, United States
6.2Okay(6)
Parking
Free Wi-Fi
Pool
Air conditioning
£499+
Check availability
Deep Blue Condo - Kahuku - Living room
Deep Blue Condo
Kahuku, O'ahu, HI, United States
8.1Very Good(18)
Parking
Free Wi-Fi
Pool
Air conditioning
£553+
Check availability
Turtle Bay Sage Ta-097-866-3424-02 Condo - Kahuku - Pool
Turtle Bay Sage Ta-097-866-3424-02 Condo
Kahuku, O'ahu, HI, United States
9.1Wonderful(3)
Parking
Free Wi-Fi
Pool
Air conditioning
£616+
Check availability
Kbm Resorts Free Car Kuilima Estates 1-Bedroom Condo With Golf Course View Inside Turtle Bay Kul-E117 - Kahuku - Living room
Kbm Resorts Free Car Kuilima Estates 1-Bedroom Condo With Golf Course View Inside Turtle Bay Kul-E117
Kahuku, O'ahu, HI, United States
8.6Very Good(11)
Parking
Free Wi-Fi
Pool
Pet-friendly
£714+
Check availability
Ko Olina Beach Villas O1001 by Gather: Ocean Tower w/ Pool, Golf & Beach Views - Kapolei - Pool
Ko Olina Beach Villas O1001 by Gather: Ocean Tower w/ Pool, Golf & Beach Views
Kapolei, O'ahu, HI, United States
9.5Wonderful(15)
Air conditioning
£804+
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Hale Hauoli Ko Olina Villa w/ Beach & Pool! - Kapolei - Balcony
Hale Hauoli Ko Olina Villa w/ Beach & Pool!
Kapolei, O'ahu, HI, United States
10Wonderful(7)
Air conditioning
£804+
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Panoramic Ocean Views in Ko Olina - Kapolei - Balcony
Panoramic Ocean Views in Ko Olina
Kapolei, O'ahu, HI, United States
10Wonderful(5)
Air conditioning
£927+
Check availability
Kbm Resorts Free Car Lxuury Ocean View Villa Palapala At Montage Kapalua Bay Daily Housekeeping Spa - Kapalua - Living room
Kbm Resorts Free Car Lxuury Ocean View Villa Palapala At Montage Kapalua Bay Daily Housekeeping Spa
Kapalua, Maui, HI, United States
10Wonderful(8)
Parking
Free Wi-Fi
Pool
Air conditioning
£2,093+
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 39 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)

August
December
£337
£304
Cheapest month to stay with an average 18% drop in price.
Most expensive month to stay with an average 53% 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 9% 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 £103. 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 £85 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 Wailea Ekahi Village - CoralTree Residence Collection and Fairway Villas Waikoloa 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
£229+
Check availability
Castle Waikiki Shore - Honolulu - Beach
Castle Waikiki Shore
Waikiki
8.5Very Good(1168)
Free Wi-Fi
Air conditioning
£255+
Check availability

Everything you need to know for your stay in Hawaii