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Hawaii Holiday Rentals

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Top Cities in Hawaii

Our top choices for Hawaii holiday rentals

1. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (460 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
The price is NZ$1,104
includes taxes & fees
1 Oct - 2 Oct
The Whaler Resort Kaanapali Beach

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,291 reviews)
"Great location!"
United States
Shad
The price is NZ$402
includes taxes & fees
10 Sept - 11 Sept
Aston Kaanapali Shores

3. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,867 reviews)
"Love this place!"
United States
Diana
The price is NZ$495
includes taxes & fees
21 Sept - 22 Sept
Napili Shores Maui by OUTRIGGER

4. The Surf Hideaway is walking distance to everything Kona

The Surf Hideaway is walking distance to everything Kona
Historic Kailua Village
9.4 out of 10, Exceptional, (127 reviews)
"Great place to stay for a night!"
United States
Anna H.
The price is NZ$260
includes taxes & fees
8 Sept - 9 Sept
The Surf Hideaway is walking distance to everything Kona

5. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (964 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is NZ$665
includes taxes & fees
4 Oct - 5 Oct
Aston Maui Hill

6. Tropical 1-bedroom cabin. Five minute drive to Hawaii Volcanoes National Park.

Tropical 1-bedroom cabin. Five minute drive to Hawaii Volcanoes National Park.
Volcano
8.6 out of 10, Excellent, (58 reviews)
"Clean place, comfortable bed, friendly host"
United States
Allison
The price is NZ$309
includes taxes & fees
7 Sept - 8 Sept
Tropical 1-bedroom cabin. Five minute drive to Hawaii Volcanoes National Park.

7. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,039 reviews)
"Beautiful property, kind staff, Dukes restaurant was awesome & located on property!! Will definitely come back again!!"
United States
Diana
The price is NZ$1,614
includes taxes & fees
3 Oct - 4 Oct
OUTRIGGER Honua Kai Resort & Spa

8. Banyan Harbor Resort

Banyan Harbor Resort
3.0 star property
Nawiliwili
8.4 out of 10, Very good, (1,275 reviews)
"Close to most of places to visit"
United States
Bernadette
The price is NZ$442
includes taxes & fees
27 Sept - 28 Sept
Banyan Harbor Resort

9. 2021 SUPREME TACOMA TRD

2021 SUPREME TACOMA TRD
1.0 star property
Anahola
The price is NZ$577
includes taxes & fees
12 Sept - 13 Sept
2021 SUPREME TACOMA TRD

10. Studio Kohala Big Island Ocean View

Studio Kohala Big Island Ocean View
Kohala Estates
9.8 out of 10, Exceptional, (255 reviews)
"We had a wonderful stay at Studio Kohala Big Island Ocean View! The space was comfortable, peaceful, and offered beautiful views. Loved listening to the wind at night! The hosts were thoughtful and welcoming, and they even provided yogurt and fresh fruit for us in the morning, which was such a nice touch. We truly enjoyed our stay and would happily return. Highly recommend!"
United States
Nichole
The price is NZ$541
includes taxes & fees
6 Sept - 7 Sept
Studio Kohala Big Island Ocean View

11. Oceanfront cottage w/ AC @ Kehena Beach, Hawaii

Oceanfront cottage w/ AC @ Kehena Beach, Hawaii
Kehena Beach Estates
9.4 out of 10, Exceptional, (64 reviews)
"We loved it"
United States
Haochen
The price is NZ$352
includes taxes & fees
9 Sept - 10 Sept
Oceanfront cottage w/ AC @ Kehena Beach, Hawaii

12. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,556 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is NZ$776
includes taxes & fees
30 Sept - 1 Oct
Aston at The Whaler on Kaanapali Beach

13. Ocean View Condo in the Heart of Kona

Ocean View Condo in the Heart of Kona
Holualoa Village
9.6 out of 10, Exceptional, (43 reviews)
"Everything was perfect!"
United States
Agassy
The price is NZ$566
includes taxes & fees
13 Sept - 14 Sept
Ocean View Condo in the Heart of Kona

14. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (306 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
The price is NZ$655
includes taxes & fees
9 Sept - 10 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

15. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,625 reviews)
"Loved the waterfront cafe and beautiful beach!"
United States
Sabrina
The price is NZ$594
includes taxes & fees
8 Sept - 9 Sept
Aston Maui Kaanapali Villas

16. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"I’ve stayed at several units in the same complex and this one was one of the best. Nicely appointed and a great view from the lanai. The bed was very comfy and the AC worked great. It’s so nice to be able to walk across the street to such a nice beach, we even saw a turtle in the water."
United States
Daniel L.
The price is NZ$585
includes taxes & fees
8 Sept - 9 Sept
Beautiful, Renovated, Hale Kamaole 159

17. HBR Family Lockoff 1206, Mountain View, Close to the Pool Add'l Resort Fees

HBR Family Lockoff 1206, Mountain View, Close to the Pool Add'l Resort Fees
Princeville
8.8 out of 10, Excellent, (108 reviews)
"We enjoyed our stay! Beautiful place. "
United States
Rhonda R.
The price is NZ$630
includes taxes & fees
13 Sept - 14 Sept
HBR Family Lockoff 1206, Mountain View, Close to the Pool Add'l Resort Fees

18. Ama'u Lani Cottage minutes from Volcano Village & Hawaii Volcanoes National Park

Ama'u Lani Cottage minutes from Volcano Village & Hawaii Volcanoes National Park
Volcano
9.6 out of 10, Exceptional, (125 reviews)
"Loved this place! Clean, quiet, fully equipped kitchen, comfortable beds, beautifully furnished. Would ddefinitely book again."
United States
Sherree F.
The price is NZ$432
includes taxes & fees
7 Sept - 8 Sept
Ama'u Lani Cottage minutes from Volcano Village & Hawaii Volcanoes National Park

19. Experience historic charm near Kailua Pier - Walk to restaurants, shops,AC,Wifi

Experience historic charm near Kailua Pier - Walk to restaurants, shops,AC,Wifi
Historic Kailua Village
9.6 out of 10, Exceptional, (224 reviews)
"I traveled s as lone and found my stay very easy"
United States
Virgilia A.
The price is NZ$441
includes taxes & fees
12 Sept - 13 Sept
Experience historic charm near Kailua Pier - Walk to restaurants, shops,AC,Wifi

20. Islander Family Studio 137, Ground Floor, Steps to Pool and Beach

Islander Family Studio 137, Ground Floor, Steps to Pool and Beach
Waipouli
9.2 out of 10, Wonderful, (119 reviews)
"Great location, close to the beach, the pool and shopping centers."
United States
Tania
The price is NZ$587
includes taxes & fees
29 Sept - 30 Sept
Islander Family Studio 137, Ground Floor, Steps to Pool and Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hawaii Hotel Reviews

Find out more about Hawaii

Everything you need to know about Hawaii holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hawaii holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hawaii holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hawaii holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hawaii. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hawaii holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hawaii holiday rentals we have selected for you start as low as NZ$349 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hawaii rentals

At Expedia, we put the best Hawaii holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hawaii rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hawaii holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hawaii. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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