Hawaii Holiday Rentals

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Top Cities in Hawaii

Top Holiday Rentals Destinations in Hawaii

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
Exterior
The Whaler Resort Kaanapali Beach
4.0 star property
9.4 out of 10, Exceptional, (27)
"Great 2 bedroom condo. Spacious and very clean. Walkable to many restaurants including Whalers village which is right next door. 2 drawbacks : shower temperature was off and hard to adjust, shower was cold for at least 5 min before becoming warm and a very loud noise was always present coming from the generators in whalers village. Our balcony was on that side and it took away from the experience of just sitting outside. Recommend u get condo unit on the opposite side. But otherwise truly a...
The Whaler Resort Kaanapali Beach
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1637)
"The only drawback is that it doesn't have a pool."
The price is NZ$1,274
per night
23 May - 24 May
Aston Waikiki Beach Tower
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Outdoor pool, pool loungers
Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (691)
"Great location, able to walk to the beach. Clean, peaceful, comfortable place to wind down after long day exploring. Would definitely stay there again if i return to Maui. "
Aston Maui Hill
Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1472)
"Amazing "
The price is NZ$1,015
per night
27 May - 28 May
Aston Mahana at Kaanapali
Cottage, 2 Bedrooms, Non Smoking | Private kitchen
Makai Club Resort
3.5 star property
9.0 out of 10, Wonderful, (254)
"One of the best places we've stayed at in our 7 trips together to Hawaii. We always stay in Princeville when in Kauai, but this will be our new go-to place now."
Makai Club Resort
Aerial view
Castle Hali'i Kai at Waikoloa
4.0 star property
9.0 out of 10, Wonderful, (628)
"Beautiful family friendly condo/resort. We found an amazing deal on this website that allowed us to enjoy a week of relaxation and exploring. The views and condition of the resort was top notch. Our only complaint was that the floors could have been cleaner. Otherwise we would recommend this place to anyone traveling with a family."
Castle Hali'i Kai at Waikoloa
4 outdoor pools
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2533)
"Loved staying and celebrating Mother’s Day and my son’s birthday! Couldn’t have asked for a better stay! "
The price is NZ$1,319
per night
4 Jun - 5 Jun
OUTRIGGER Honua Kai Resort & Spa
On the beach
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1470)
"Very clean and pretty!!! Staff is very helpful and friendly! Would recommend to anyone!!"
Napili Shores Maui by OUTRIGGER
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, pool loungers
The Cliffs at Princeville
3.5 star property
8.8 out of 10, Excellent, (186)
"A very beautiful place. Next time we will book a longer stay."
The price is NZ$659
per night
1 Jun - 2 Jun
The Cliffs at Princeville
View from room
Aston Kona by the Sea
4.0 star property
8.8 out of 10, Excellent, (978)
"This resort was relaxing and enjoyable. I would definitely stay here again if I had the opportunity. The only reason that I did not give it a perfect review was due to the really weird design of the window in the bedroom. It was a corner window that faced into the outdoor entrance to the condo. We always had to keep the blackout curtains tightly shut. Now, the patio on the other side facing the pool and the ocean made up for it. This is where we spent our time when we were in the condo. It was...
The price is NZ$461
per night
24 May - 25 May
Aston Kona by the Sea
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3004)
"Parking spots are quite small. Luckily we had a small car. "
The price is NZ$459
per night
27 May - 28 May
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
3.0 star property
8.6 out of 10, Excellent, (2152)
"Very comfortable, big rooms and very peaceful!"
The price is NZ$459
per night
24 May - 25 May
Aston Maui Kaanapali Villas
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (331)
"I liked pretty much the whole experience of staying at this property."
The price is NZ$444
per night
22 May - 23 May
Royal Kuhio
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (692)
"We had an amazing time. We will book again in the future"
The price is NZ$655
per night
7 Jun - 8 Jun
Hilton Grand Vacations Club at Hilton Hawaiian Village
Suite, 1 Bedroom
The Gardens at West Maui
3.0 star property
8.4 out of 10, Very good, (375)
"We loved staying here!!! The best location- walkable to Napili and Kapalua. Clean, nice pool and hot tub. We will definitely be back!!"
The Gardens at West Maui
2 Bedrooms, 2 Bath Oceanfront
Castle Kaha Lani Resort
3.0 star property
8.4 out of 10, Very good, (685)
"Good- location and cleanliness. Bad-no AC "
Castle Kaha Lani Resort
Exterior
Kiahuna Plantation Resort Kauai by OUTRIGGER
3.0 star property
8.4 out of 10, Very good, (852)
"This our 2nd time at Kiahuna Plantation. We are experienced travelers that don't want or need to be "pampered", so we like the ability to have a kitchen and cook local foods, and the opportunity to do our own planning of our vacation experience. This isn't the fanciest place, but by comparison it is a good value. The grounds are beautiful and the beach is better, bigger and less crowded than Poipu Beach (which is also easily accessible by walking). If you want an all-inclusive, upscale...
Kiahuna Plantation Resort Kauai by OUTRIGGER
Condo, 2 Bedrooms, Oceanfront | View from room
Royal Sea Cliff Kona by OUTRIGGER
3.0 star property
8.4 out of 10, Very good, (429)
"Excellent property, and wonderful, helpful staff. We had an ocean front room, which was amazing. The pool is great for kids and adults alike. The property is also located a little away from the busy part of Ali’i drive, which makes it great to relax at the end of the day after a day full of activities but is conveniently located near beaches and grocery/convenient stores. I highly recommend the property to anyone planning a trip to Kona."
Royal Sea Cliff Kona by OUTRIGGER
Standard Room, 1 Bedroom | Living area
Kahana Beach Vacation Club
3.0 star property
8.2 out of 10, Very good, (542)
"Probably one of the cleanest rooms I’ve stayed in. The balcony directly faced the ocean with Molokai in full view."
Kahana Beach Vacation Club
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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.

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$205 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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