Hawaii holiday rentals

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Booking Insights
Recommended by KAYAK

Best Hawaii holiday rentals

Shores at Waikoloa Bungalow 225 - Waikoloa Village - Living room
Shores at Waikoloa Bungalow 225
Waikoloa Village, The Big Island, HI, United States
Pool
Air conditioning
Big Island Waikoloa Hills 604 1 Bedroom Condo - Waikoloa Village - Living room
Big Island Waikoloa Hills 604 1 Bedroom Condo
Waikoloa Village, The Big Island, HI, United States
Condo
Free Wi-Fi
Nona Lani Cottages - Kīhei - Balcony
Nona Lani Cottages
Kīhei, Maui, HI, United States
Parking
Free Wi-Fi
Air conditioning
Colony Villas at Waikoloa Beach Resort 1305 - Waikoloa Village - Pool
Colony Villas at Waikoloa Beach Resort 1305
Waikoloa Village, The Big Island, HI, United States
Free Wi-Fi
Pool
Air conditioning
Kanai A Nalu 210 - Wailuku - Balcony
Kanai A Nalu 210
Wailuku, Maui, HI, United States
Parking
Free Wi-Fi
Pool
Air conditioning
Fairway Villas Waikoloa F6 - Waikoloa Village - Dining room
Fairway Villas Waikoloa F6
Waikoloa Village, The Big Island, HI, United States
Parking
Free Wi-Fi
Pool
Air conditioning
Castle Waikiki Shore - Honolulu - Beach
Free Wi-Fi
Air conditioning
Ever Kauwela Llc. Hawaii. - Waikoloa Village - Patio
Ever Kauwela Llc. Hawaii.
Waikoloa Village, The Big Island, HI, United States
Parking
Free Wi-Fi
Air conditioning
PiH Ocean Gem Villa Ocean Front Walk to Private Beach Club Bikes - Waikoloa Village - Balcony
PiH Ocean Gem Villa Ocean Front Walk to Private Beach Club Bikes
Waikoloa Village, The Big Island, HI, United States
Parking
Free Wi-Fi
Air conditioning
Fairway S Waikoloa F6 3 Bedroom Villa by RedAwning - Waikoloa Village - Dining room
Fairway S Waikoloa F6 3 Bedroom Villa by RedAwning
Waikoloa Village, The Big Island, HI, United States
Free Wi-Fi
Marriott's Ko Olina Beach Club 1BR Apartment with Resort Access - Kapolei
Free Wi-Fi
Pool
Air conditioning
Luxury Waikoloa Retreat: 3br! - Waikoloa Village
Luxury Waikoloa Retreat: 3br!
Waikoloa Village, The Big Island, HI, United States
Parking
Free Wi-Fi
Pool
Air conditioning
Roadtrip Camping on Maui - Kahului
Roadtrip Camping on Maui
Kahului, Maui, HI, United States
8.4Very Good(7)
Luxury Tent
Air conditioning
Unit 9 Waena Inn Newly Renovated Maui Private Suite - Wailuku
Parking
Free Wi-Fi
Air conditioning
Star of Waikoloa Beach Resort - Ainamalu House - Waikoloa Village
Star of Waikoloa Beach Resort - Ainamalu House
Waikoloa Village, The Big Island, HI, United States
Air conditioning
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.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
May
£365
£357
Cheapest month to stay with an average 22% drop in price.
Most expensive month to stay with an average 24% 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 5 days.
  • The cheapest Hawaii holiday rental found on KAYAK in the last 2 weeks was £102, while the most expensive was £106.
  • Pool, beachfront, air-conditioned, and kitchen/kitchenette are the most popular holiday rental property amenities in Hawaii
  • Holiday rentals in Hawaii are around 13% 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 (41% of total searches to Hawaii). The next most popular destinations are Honolulu (33%) and Kailua-Kona (8%). Searches for holida rentals in Kapalua (4%), Princeville (3%) and Kīhei (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 £95. 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, campgrounds, lodges, motorhomes, cabins, 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 Waikiki Shore 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 homes that can sleep 6 people or more by KAYAK users are Elua Village and Shores at Waikoloa.

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.