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West Side Holiday Rentals

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Our top choices for West Side holiday rentals

White Sand Beaches on the Sunny Westside of Kauai.

White Sand Beaches on the Sunny Westside of Kauai.
Kekaha
9.6 out of 10, Exceptional, (148)
"The owners were so accommodating. Loved this cute beach house. Our family felt so welcomed, the best vibes. Highly recommend. "
United States
Katie H.
The price is NZ$1,125
includes taxes & fees
31 Dec - 1 Jan 2026
White Sand Beaches on the Sunny Westside of Kauai.

Plantation Hale Suites

Plantation Hale Suites
3.0 star property
Waipouli
8.0 out of 10, Very good, (1670)
"Room was clean and had all the amenities needed for a wonderful stay!"
United States
David
The price is NZ$553
includes taxes & fees
11 Jan - 12 Jan 2026
Plantation Hale Suites

Banyan Harbor Resort

Banyan Harbor Resort
3.0 star property
Nawiliwili
8.6 out of 10, Excellent, (1125)
"Was nice"
United States
Sanjeev
The price is NZ$585
includes taxes & fees
1 Jan - 2 Jan 2026
Banyan Harbor Resort

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

Islander Family Studio 137, Ground Floor, Steps to Pool and Beach
Waipouli
9.4 out of 10, Exceptional, (97)
"Great location"
United States
Billy F.
The price is NZ$572
includes taxes & fees
5 Jan - 6 Jan 2026
Islander Family Studio 137, Ground Floor, Steps to Pool and Beach

Amazing Studio By The Beach! 1BR

Amazing Studio By The Beach! 1BR
Waipouli
9.0 out of 10, Wonderful, (44)
"Great little room right next to the beach!"
United States
Jasmine G.
The price is NZ$616
includes taxes & fees
19 Jan - 20 Jan 2026
Amazing Studio By The Beach! 1BR

Oceanfront on Kauai starting at $140/night!

Oceanfront on Kauai starting at $140/night!
Waipouli
9.6 out of 10, Exceptional, (264)
"We enjoyed our stay. We loved being right on the ocean with the pool right out the back door. We saw spinner dolphins one morning from our lanai. The condo was clean and we loved the location. If your looking for view and location and cleanliness this is the place to stay. If your looking for lavish and top of the line you would be disappointed but luckily that's not us so this was perfect. I definitely can see us staying here again if someday we make it back to Kauai."
United States
MYRNA L H.
The price is NZ$724
includes taxes & fees
23 Jan - 24 Jan 2026
Oceanfront on Kauai starting at $140/night!

The Cliffs at Princeville

The Cliffs at Princeville
3.5 star property
Princeville
8.8 out of 10, Excellent, (246)
"The rooms are beautiful, clean and inviting. The staff was attentive to needs and friendly"
United States
Kathleen
The Cliffs at Princeville

Charming Beachfront Condo! 2BR

Charming Beachfront Condo! 2BR
Waipouli
9.8 out of 10, Exceptional, (58)
"Great location right on the water!"
United States
M R.
The price is NZ$923
includes taxes & fees
17 Jan - 18 Jan 2026
Charming Beachfront Condo! 2BR

Couples Studio 1205, Mt View, Kitchenette, Washer Dryer, Add'l Resort Fees

Couples Studio 1205, Mt View, Kitchenette, Washer Dryer, Add'l Resort Fees
Princeville
9.4 out of 10, Exceptional, (117)
"Wonderful place with an amazing view. The pool is spectacular as is the beach. We loved everything and looking forward to coming back. "
United States
Martin A.
The price is NZ$823
includes taxes & fees
3 Jan - 4 Jan 2026
Couples Studio 1205, Mt View, Kitchenette, Washer Dryer, Add'l Resort Fees

Cozy Studio By The Beach! 1BR

Cozy Studio By The Beach! 1BR
Waipouli
9.4 out of 10, Exceptional, (42)
"Our stay at David's was wonderful. There was a leak in the AC when we first turned it on due to the drastic temperature change, but David immediately called and he and his daughter came by 30 minutes later to install a drip catcher panel. Shampoo/conditioner/soap all provided, as well as some dishware. Location was great, right across the street from Safeway and Wailua shave ice. Would stay here again!"
United States
Nicole L.
The price is NZ$711
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Studio By The Beach! 1BR

Tropical, Bright Studio: Steps to Golf Course, Beaches, & Amazing Views

Tropical, Bright Studio: Steps to Golf Course, Beaches, & Amazing Views
Princeville
9.4 out of 10, Exceptional, (106)
"This place was cute, clean and great location. We enjoyed our stay!"
United States
Caroline d.
Tropical, Bright Studio: Steps to Golf Course, Beaches, & Amazing Views

Sandpiper 129A - Updated, modern, comfortable 1 bd

Sandpiper 129A - Updated, modern, comfortable 1 bd
Princeville
10.0 out of 10, Exceptional, (153)
"The atmosphere was excellent. We could enjoy the beautiful sunset every evening and cute nenes too."
Japan
Yoshiko
Sandpiper 129A - Updated, modern, comfortable 1 bd

Adorable Studio, sleeps 3 - Totally renovated in 2018

Adorable Studio, sleeps 3 - Totally renovated in 2018
Princeville
9.4 out of 10, Exceptional, (150)
"Cute and quiet place to stay! The area is walkable and a close driving distance from many nearby beaches, shopping, and food. It was easy to navigate and checking in and out was a breeze. The place was clean and served its purpose for my trip!"
United States
Harley
The price is NZ$439
includes taxes & fees
4 Jan - 5 Jan 2026
Adorable Studio, sleeps 3 - Totally renovated in 2018

Direct Ocean Front, Top Floor Studio Paradise

Direct Ocean Front, Top Floor Studio Paradise
Waipouli
10.0 out of 10, Exceptional, (135)
"We had a great stay! The toaster oven was nice for making some meals in the room. Great location. Coconut marketplace was handy to have next door. Would book again."
United States
Skye O.
The price is NZ$619
includes taxes & fees
15 Jan - 16 Jan 2026
Direct Ocean Front, Top Floor Studio Paradise

Beautiful Air Conditioned 2nd Floor 2 Bedroom w/mountain and slight ocean view

Beautiful Air Conditioned 2nd Floor 2 Bedroom w/mountain and slight ocean view
Waipouli
9.8 out of 10, Exceptional, (37)
"Condo was very nice, great owners to work with."
United States
Jill B.
Beautiful Air Conditioned 2nd Floor 2 Bedroom w/mountain and slight ocean view

Dreamy Beachfront Studio! 1BR

Dreamy Beachfront Studio! 1BR
Waipouli
9.6 out of 10, Exceptional, (24)
"Great location, well stocked, clean. "
United States
Sanjay
Dreamy Beachfront Studio! 1BR

HBR Couples Lockoff 7201, Ocean View, Quiet Location, Add'l Resort Fees

HBR Couples Lockoff 7201, Ocean View, Quiet Location, Add'l Resort Fees
Princeville
8.2 out of 10, Very good, (71)
"Had a great time! Resort was very clean and had great amenities including two nice pools. It is very hilly but they offer golf cart pickups for getting around. Wifi and cell signal can be spotty at times. Would definitely stay here again!"
United States
Tony T.
The price is NZ$705
includes taxes & fees
7 Jan - 8 Jan 2026
HBR Couples Lockoff 7201, Ocean View, Quiet Location, Add'l Resort Fees

H-G-T-V type Renovation, Million Dollar view starting at only $210/night!

H-G-T-V type Renovation, Million Dollar view starting at only $210/night!
Waipouli
9.8 out of 10, Exceptional, (228)
"Perfect property with a stunning ocean view right out the patio door! The condo is situated within walking distance to many restaurants and the Coconut Marketplace Shopping area. The location was also centrally located for visiting the northern beaches, as well as all of the southern beaches. The condo was outfitted with everything we needed, including beach chairs and umbrella for beach days. We definitely recommend this place!"
United States
Liz
The price is NZ$711
includes taxes & fees
3 Jan - 4 Jan 2026
H-G-T-V type Renovation, Million Dollar view starting at only $210/night!

Sandpiper 133A - Updated (2021) one bedroom, sleeps 4.

Sandpiper 133A - Updated (2021) one bedroom, sleeps 4.
Princeville
9.6 out of 10, Exceptional, (57)
"Best time ever. Love this island so much! "
United States
William K.
The price is NZ$719
includes taxes & fees
20 Jan - 21 Jan 2026
Sandpiper 133A - Updated (2021) one bedroom, sleeps 4.

Ocean-View Studio, Steps from Beaches In Sunny Poipu

Ocean-View Studio, Steps from Beaches In Sunny Poipu
Poipu
9.8 out of 10, Exceptional, (217)
"Place was quiet, clean and just right for our needs."
United States
Bryan D.
The price is NZ$975
includes taxes & fees
22 Jan - 23 Jan 2026
Ocean-View Studio, Steps from Beaches In Sunny Poipu
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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Find out more about West Side

Everything you need to know about West Side 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 West Side 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 West Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

West Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Side. 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 West Side 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 West Side holiday rentals we have selected for you start as low as NZ$410 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Side rentals

At Expedia, we put the best West Side 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 West Side 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 West Side 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 West Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.