Hawaii holiday rentals

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Booking Insights
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Best Hawaii holiday rentals

Gardens At West Maui - Kapalua - Bedroom
Gardens At West Maui
Kapalua, Maui, HI, United States
7.8Good(157)
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
£222+
Check availability
Kapalua Golf Villas 27t1 · Kgv 27t1 Luxurious Kapalua Villa With - Kapalua - Balcony
Kapalua Golf Villas 27t1 · Kgv 27t1 Luxurious Kapalua Villa With
Kapalua, Maui, HI, United States
9.8Wonderful(13)
Condo
Parking
Free Wi-Fi
Air conditioning
£301+
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(76)
Apartment
Free Wi-Fi
£345+
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Kapalua Bay Villas 33g2 · Kbv 33g2 Renovated 1bd Oceanfront Vill - Kapalua - Dining room
Kapalua Bay Villas 33g2 · Kbv 33g2 Renovated 1bd Oceanfront Vill
Kapalua, Maui, HI, United States
9.7Wonderful(27)
Condo
Parking
Free Wi-Fi
Air conditioning
£968+
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Minutes To Hamoa Beach, Best Location In Hana - Hana - Pool
Minutes To Hamoa Beach, Best Location In Hana
Hana, Maui, HI, United States
9.8Wonderful(65)
Cottage
Free Wi-Fi
£378+
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Kbm Resorts Free Car Beach Villas at Ko Olina 2-Bedroom Beachfront Villa Bvk-B-308 - Kapolei - Balcony
Kbm Resorts Free Car Beach Villas at Ko Olina 2-Bedroom Beachfront Villa Bvk-B-308
Kapolei, O'ahu, HI, United States
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
£1,045+
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Arnott's Lodge & Hiking Adventures - Hilo - Living room
Arnott's Lodge & Hiking Adventures
Hilo, The Big Island, HI, United States
7.8Good(319)
Lodge
Parking
Free Wi-Fi
Air conditioning
£129+
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Hana Kai Maui - #106 Kuakahi partial oceanview studio - Hana - Building
Hana Kai Maui - #106 Kuakahi partial oceanview studio
Hana, Maui, HI, United States
8.3Very Good(29)
Apartment
Parking
Free Wi-Fi
£375+
Check availability
End of year specials! OT302- 3rd flr 3 BR- Sleeps 8 - Kapolei - Building
End of year specials! OT302- 3rd flr 3 BR- Sleeps 8
Kapolei, O'ahu, HI, United States
9.3Wonderful(16)
Villa
Air conditioning
£921+
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Hana Kai Maui - #105 Kaihalulu - Hana - Bedroom
Hana Kai Maui - #105 Kaihalulu
Hana, Maui, HI, United States
9.4Wonderful(38)
Apartment
Parking
Free Wi-Fi
£393+
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Marriott's Ko Olina Beach Club Studio Inquire Before Making Reservation Request - Kapolei - Lobby
Marriott's Ko Olina Beach Club Studio Inquire Before Making Reservation Request
Kapolei, O'ahu, HI, United States
9.8Wonderful(131)
Apartment
Air conditioning
£407+
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Studio Marriott's Ko Olina - Kapolei - Bedroom
Studio Marriott's Ko Olina
Kapolei, O'ahu, HI, United States
Apartment
Pool
Air conditioning
£430+
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Villa Olina 3-Bedroom Walking Distance From Lagoons 30-day Minimum Vacation Rental - Kapolei - Pool
Villa Olina 3-Bedroom Walking Distance From Lagoons 30-day Minimum Vacation Rental
Kapolei, O'ahu, HI, United States
9.9Wonderful(14)
Villa
Parking
Free Wi-Fi
Pool
Pet-friendly
£575+
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Hana Kai Maui - #206 Puhele, lofted studio - Hana - Balcony
Hana Kai Maui - #206 Puhele, lofted studio
Hana, Maui, HI, United States
9.4Wonderful(21)
Apartment
Parking
Free Wi-Fi
£423+
Check availability
Marriott's Ko Olina Beach Club 1BR Apartment with Resort Access - Kapolei
Marriott's Ko Olina Beach Club 1BR Apartment with Resort Access
Kapolei, O'ahu, HI, United States
10Wonderful(2)
House
Free Wi-Fi
Pool
Air conditioning
£557+
Check availability
Ko Olina Beach Villas B102 - Kapolei
Ko Olina Beach Villas B102
Kapolei, O'ahu, HI, United States
Apartment
Parking
Free Wi-Fi
Pool
Air conditioning
£869+
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 43 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)

October
December
£352
£382
Cheapest month to stay with an average 26% drop in price.
Most expensive month to stay with an average 7% 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 November.
  • 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 £105, while the most expensive was £168.
  • Beachfront, pool, air-conditioned, and kitchen/kitchenette are the most popular holiday rental property amenities in Hawaii
  • Holiday rentals in Hawaii are around 19% 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 (34%) and Kailua-Kona (7%). Searches for holida rentals in Kapalua (4%), Princeville (2%) 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 £116. 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, 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 Fairway Villas Waikoloa By Outrigger.

  • 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 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.

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
Stay Condominiums Waikiki
Waikiki
6.2Okay(287)
Free Wi-Fi
Air conditioning
£208+
Check availability
Castle Waikiki Shore - Honolulu - Beach
Castle Waikiki Shore
Waikiki
8.5Very Good(1206)
Apartment
Free Wi-Fi
Air conditioning
£218+
Check availability

Everything you need to know for your stay in Hawaii