A coastal landscape with rugged cliffs, dense greenery, and a clear blue sea.

Search Vacation Homes in West Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for West Side vacation homes

A white sofa in a room with a large window, a wooden door, and a wall-mounted sign reading "ALOHA".

1. 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, (159 reviews)
"Great location, host, and HoCo treated us every morning."
United States
Kent K.
The price is ￥43,626
￥98,397 total
includes taxes & fees
Nov 21 - Nov 22
White Sand Beaches on the Sunny Westside of Kauai.
A two-story house with a balcony, a garage, and a well-maintained lawn.

2. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.4 out of 10, Exceptional, (83 reviews)
"Property was comfortable, clean, and easy to find. Would stay here again. Host provided lots of extra amenities."
United States
Melissa C.
The price is ￥21,883
￥68,152 total
includes taxes & fees
Nov 5 - Nov 6
An Affordable Alternative to Expensive Accommodations in Poipu
A well-maintained garden with a pathway leading to a building, palm trees, and a view of the ocean.

3. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (115 reviews)
"Had a great stay! We really liked the unit and the location. Everything was clean and comfy, and the host was super friendly. Would definitely stay here again."
United States
Myranda S.
The price is ￥21,883
￥68,152 total
includes taxes & fees
Nov 5 - Nov 6
An Affordable Alternative to Expensive Accommodations in Poipu
A residential area with houses, a road, and a view of mountains and a lake.

4. Peaceful Hawaiian Hideout Minutes to Hanalei town!

Peaceful Hawaiian Hideout Minutes to Hanalei town!
Princeville
10.0 out of 10, Exceptional, (4 reviews)
"Thalia was a lovely home. Beautifully renovated and everything was nice, new and clean. Great location for north shore exploration. Close to Hanalei and Princeville. Communication and courtesy were great. Would stay again!"
United States
Bobette N.
The price is ￥42,214
￥105,702 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful Hawaiian Hideout Minutes to Hanalei town!
A pool area with a wooden deck, surrounded by tropical plants and a mountain backdrop.

5. Romantic Cottage, Private Acre of Paradise, View! Pool!

Romantic Cottage, Private Acre of Paradise, View! Pool!
Hanalei
9.8 out of 10, Exceptional, (112 reviews)
"This is an amazing little corner of paradise with a view and everything you need."
United States
Jennifer D.
The price is ￥77,651
￥179,075 total
includes taxes & fees
Oct 31 - Nov 1
Romantic Cottage, Private Acre of Paradise, View! Pool!
A pool area with a waterfall feature, surrounded by a stone deck and palm trees.

6. Kauai Beach Resort Ocean View | Pools, Waterslide, Hot Tub, Spa, King Bed, AC

Kauai Beach Resort Ocean View | Pools, Waterslide, Hot Tub, Spa, King Bed, AC
Lihue
4.0 out of 10, (1 review)
"Unpleasant stay. Don’t intend to return. Not terrible, but not close to being worth the price tag."
Brazil
João
The price is ￥12,667
￥91,684 total
includes taxes & fees
Oct 29 - Oct 30
Kauai Beach Resort Ocean View | Pools, Waterslide, Hot Tub, Spa, King Bed, AC
A spacious living area with a dining set, a ceiling fan, and a large window overlooking a garden.

7. Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi

Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi
Princeville
9.4 out of 10, Exceptional, (133 reviews)
"This is a great place to stay, in a great area on the island. The condo had everything we needed, and is decorated nicely with Hawaiian charm. "
United States
Kevin M.
The price is ￥29,805
￥92,286 total
includes taxes & fees
Oct 27 - Oct 28
Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi
A grassy area with two chairs and trees overlooking a body of water.

8. E2: 1 bedroom, 1st floor, oceanfront

E2: 1 bedroom, 1st floor, oceanfront
Princeville
8.6 out of 10, Excellent, (40 reviews)
"Very nice, clean, lots of amenities"
United States
Anonymous traveler
The price is ￥40,410
￥94,963 total
includes taxes & fees
Oct 27 - Oct 28
E2: 1 bedroom, 1st floor, oceanfront
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

9. *NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC

*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC
Poipu
6.0 out of 10, (1 review)
The price is ￥37,636
￥122,078 total
includes taxes & fees
Oct 26 - Oct 27
*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC
A spacious open-plan living area with a kitchen, dining table, and seating area.

10. Ocean & Golf Course Views / 2BR 2BA Princeville Townhouse / Walk to Beach / WiFi

Ocean & Golf Course Views / 2BR 2BA Princeville Townhouse / Walk to Beach / WiFi
Princeville
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful location and great accommodations. Mahalo for letting us stay there. "
United States
Rachelle R.
The price is ￥37,108
￥101,942 total
includes taxes & fees
Oct 26 - Oct 27
Ocean & Golf Course Views / 2BR 2BA Princeville Townhouse / Walk to Beach / WiFi
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

11. *NEW Poipu 2BR Retreat|Pool|AC & Athletic Club

*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Poipu
10.0 out of 10, Exceptional, (23 reviews)
"The house was beautiful, the location was great! And getting to go to the athletic club was such a wonderful bonus. Would absolutely stay here again!!!"
United States
Camille H.
The price is ￥37,636
￥111,208 total
includes taxes & fees
Oct 27 - Oct 28
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
A two-story house with a balcony, a patio with outdoor furniture, and a well-lit interior.

12. 🏝Princeville Bliss, Huge Lanai - 3 bedroom, 4 queens, sleeps 10 🐠

🏝Princeville Bliss, Huge Lanai - 3 bedroom, 4 queens, sleeps 10 🐠
Princeville
9.4 out of 10, Exceptional, (16 reviews)
"Family friendly"
United States
Cindy W.
The price is ￥39,390
￥104,977 total
includes taxes & fees
Oct 26 - Oct 27
🏝Princeville Bliss, Huge Lanai - 3 bedroom, 4 queens, sleeps 10 🐠
A spacious living area with a high ceiling, wooden flooring, a large sofa, a coffee table, and a dining area with chairs and a table.

13. Walk to Hanalei Bay&Town. Waterfalls&Mountain Views. A/C, FREE Surf,Sup,Bike.etc

Walk to Hanalei Bay&Town. Waterfalls&Mountain Views. A/C, FREE Surf,Sup,Bike.etc
Hanalei
10.0 out of 10, Exceptional, (72 reviews)
"Absolutely beautiful - inside and out, we felt we were in a true Kaua’i escape! Took 1000 pictures just in the yard - landscaping is phenomenal with the surfboard fencing! Perfect walk to beach, food, and some shopping! Hosts were very easy to communicate with and the house was loaded with all the towels, beach toys, and simple needs of staying in a VRBO! Would stay here again!"
United States
Patty G.
The price is ￥188,244
￥335,410 total
includes taxes & fees
Nov 1 - Nov 2
Walk to Hanalei Bay&Town. Waterfalls&Mountain Views. A/C, FREE Surf,Sup,Bike.etc
An aerial view of a resort with a central swimming pool, tennis courts, and a landscaped area with umbrellas.

14. 🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠

🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
Poipu
9.4 out of 10, Exceptional, (35 reviews)
"Will stay there again"
United States
Dayne O.
The price is ￥35,155
￥85,876 total
includes taxes & fees
Oct 27 - Oct 28
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
A modern kitchen with white cabinetry, a central island, and a dining area with a sofa and coffee table.

15. Cycle or Walk to Hanalei Bay

Cycle or Walk to Hanalei Bay
Hanalei
10.0 out of 10, Exceptional, (75 reviews)
"Place was nice!"
United States
Carley
The price is ￥145,673
￥288,928 total
includes taxes & fees
Oct 26 - Oct 27
Cycle or Walk to Hanalei Bay
A balcony with a view of a golf course, mountains, and a lake.

16. Magical views of Hanalei Bay, Napali Coast and the Makai Golf Course in a beautifully styled home

Magical views of Hanalei Bay, Napali Coast and the Makai Golf Course in a beautifully styled home
Princeville
10.0 out of 10, Exceptional, (36 reviews)
"Absolutely beautiful views of the valley, great and comfortable home, full kitchen with laundry at home, walking distance from the beautiful Hanalei beach"
United States
Deepti
The price is ￥54,766
￥151,166 total
includes taxes & fees
Oct 26 - Oct 27
Magical views of Hanalei Bay, Napali Coast and the Makai Golf Course in a beautifully styled home
A residential area with houses, a wooden deck, and a mountain backdrop.

17. Hanalei Treehouse: Mountain, Waterfall & Bay Views

Hanalei Treehouse: Mountain, Waterfall & Bay Views
Princeville
9.4 out of 10, Exceptional, (27 reviews)
"We had an amazing stay at the property. The location and views are great. Would totally stay here again."
United States
Jesus Y.
The price is ￥50,983
￥143,486 total
includes taxes & fees
Oct 26 - Oct 27
Hanalei Treehouse: Mountain, Waterfall & Bay Views
A modern kitchen with white cabinetry, a wooden island, and a view to a balcony.

18. New Listing! Luxurious 4BR/3BA House with AC

New Listing! Luxurious 4BR/3BA House with AC
Poipu
10.0 out of 10, Exceptional, (25 reviews)
"Great location, loved the house, host communication was great. I would definitely stay here again!"
United States
Janine H.
The price is ￥68,960
￥223,223 total
includes taxes & fees
Nov 19 - Nov 20
New Listing! Luxurious 4BR/3BA House with AC
A covered outdoor seating area with wicker furniture and a table with fruit.

19. Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!

Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
Princeville
9.6 out of 10, Exceptional, (124 reviews)
"Nice, very convenient place, had everything we needed."
United States
Katya G.
The price is ￥49,273
￥208,286 total
includes taxes & fees
Oct 26 - Oct 27
Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
A modern kitchen with white cabinets, a wooden dining table, and a large window overlooking a backyard with a pool.

20. Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu

Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu
Princeville
9.8 out of 10, Exceptional, (18 reviews)
"Love this house! It was super cute. Layout was perfect and the game room and pool were the perfect addition for a rainy afternoon."
United States
christy b.
The price is ￥74,327
￥193,554 total
includes taxes & fees
Oct 29 - Oct 30
Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Side Hotel Reviews

Sheraton Kauai Resort Villas

Sheraton Kauai Resort Villas

10/10 Excellent
"Clean room"
Joe 1-night trip
Posted 3 hours ago
Sheraton Kauai Resort Villas

Find out more about West Side

West Side Vacation Homes information

Number of reviews
808
Accommodation
544 Vacation Homes
Lowest Price
￥68,152
Highest Price
￥335,410

Explore a world of travel with Expedia