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

Holiday Homes in West Side

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for West Side holiday homes

A swimming pool with a tiled edge, surrounded by lounge chairs and palm trees.

1. 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 NZ$836
includes taxes & fees
15 Oct - 16 Oct
An Affordable Alternative to Expensive Accommodations in Poipu
A tropical resort pool with a water slide, surrounded by lush greenery and palm trees.

2. *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 NZ$1,173
includes taxes & fees
24 Sept - 25 Sept
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
A residential area with a pond, lush greenery, and houses with sloped roofs.

3. *New* Fall Deal Princeville 2BR Retreat with Pool, Hot Tub and Lanai

*New* Fall Deal Princeville 2BR Retreat with Pool, Hot Tub and Lanai
Princeville
The price is NZ$1,422
includes taxes & fees
24 Sept - 25 Sept
*New* Fall Deal Princeville 2BR Retreat with Pool, Hot Tub and Lanai
A rocky shoreline with clear water, palm trees, and a distant view of the ocean.

4. 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, (132 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 NZ$1,023
includes taxes & fees
29 Sept - 30 Sept
Island Vibes! / 2BR 2BA Princeville Townhouse / Walk to Beach / Fast WiFi
A covered outdoor area with a wooden deck, a sliding glass door leading to a patio, and lush greenery in the background.

5. 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 NZ$1,040
includes taxes & fees
1 Oct - 2 Oct
Peaceful Hawaiian Hideout Minutes to Hanalei town!
A beach with clear blue water, sandy shore, and lush green hills in the background.

6. 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 NZ$2,169
includes taxes & fees
24 Oct - 25 Oct
Romantic Cottage, Private Acre of Paradise, View! Pool!
A swimming pool with a mosaic tile design, surrounded by lounge chairs and a palm tree.

7. An Affordable Alternative to Expensive Accommodations in Poipu

An Affordable Alternative to Expensive Accommodations in Poipu
Poipu
9.2 out of 10, Wonderful, (114 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 NZ$896
includes taxes & fees
24 Sept - 25 Sept
An Affordable Alternative to Expensive Accommodations in Poipu
A bedroom with a large window overlooking the ocean, a balcony with a table and chairs, and a wooden floor.

8. B10: 1 bedroom, 3rd floor, oceanview

B10: 1 bedroom, 3rd floor, oceanview
Princeville
8.8 out of 10, Excellent, (66 reviews)
"View of the ocean from the deck and inside daybed by window are what truly make this unit stand out. The nearby Foodland has excellent food choices prepared or to cook at home, which was nice because it rained often during our stay. "
United States
David W.
The price is NZ$1,061
includes taxes & fees
1 Oct - 2 Oct
B10: 1 bedroom, 3rd floor, oceanview
A wooden deck with a hot tub, lounge chairs, and a covered area with a view of lush greenery and mountains.

9. The Iconic Bamboo House

The Iconic Bamboo House
Hanalei
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. Close walk to beach. They had sand chairs, an umbrella, some toys and boogie boards to borrow which was amazing. The property texted me before check in. I texted back to verify they had boogie boards to borrow, they told me no they did not have boogie boards to borrow. So I bought a non refundable 75 boogie board (all of them are expensive high quality material) only to realize I did not need it. Frustrating. (Boogie boards all sales final)The place was clean. There was...
United States
Jessica J.
The price is NZ$2,486
includes taxes & fees
24 Sept - 25 Sept
The Iconic Bamboo House
A two-story house with a balcony, a patio with outdoor furniture, and a well-lit interior.

10. 🏝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 NZ$1,171
includes taxes & fees
5 Oct - 6 Oct
🏝Princeville Bliss, Huge Lanai - 3 bedroom, 4 queens, sleeps 10 🐠
A beach with clear turquoise water, a sandy shore, and lush green mountains in the background.

11. Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates

Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates
Poipu
9.8 out of 10, Exceptional, (151 reviews)
"Quiet, private, clean home! Have stayed here twice now and recommend it to anyone going to the island. Has everything you need for a comfy stay."
United States
Madison H.
The price is NZ$1,007
includes taxes & fees
11 Oct - 12 Oct
Hale Minoaka | Private Cottage w/ A/C & Bikes in Poipu Beach Estates
A covered outdoor seating area with wicker furniture and a table with fruit.

12. 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, (123 reviews)
"Nice, very convenient place, had everything we needed."
United States
Katya G.
The price is NZ$2,297
includes taxes & fees
3 Oct - 4 Oct
Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
A beach with a person lying on a towel under a tree, a rocky cliff, and the ocean.

13. 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, (32 reviews)
"Beautiful location and great accommodations. Mahalo for letting us stay there. "
United States
Rachelle R.
The price is NZ$1,067
includes taxes & fees
28 Sept - 29 Sept
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.

14. *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 NZ$1,305
includes taxes & fees
28 Sept - 29 Sept
*NEW 2BD Luxe Beach Cottage |Pool PickleB Gym| AC
A modern kitchen with a large island, stainless steel appliances, and white cabinetry.

15. AC IN ALL 4 BEDROOMS! Recently renovated 4BD/3B Queen's Bath home w/Jacuzzi!

AC IN ALL 4 BEDROOMS! Recently renovated 4BD/3B Queen's Bath home w/Jacuzzi!
Princeville
10.0 out of 10, Exceptional, (13 reviews)
"The hosts were amazing and very responsive. The house was very beautiful and had everything you could need! We loved our stay. "
United States
Brooke F.
AC IN ALL 4 BEDROOMS! Recently renovated 4BD/3B Queen's Bath home w/Jacuzzi!
A modern bathroom with a freestanding bathtub, a showerhead, and lush greenery.

16. 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 NZ$3,614
includes taxes & fees
4 Oct - 5 Oct
Walk to Hanalei Bay&Town. Waterfalls&Mountain Views. A/C, FREE Surf,Sup,Bike.etc
A pool with a water slide, surrounded by rocks and tropical plants.

17. 🏝 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, (33 reviews)
"The property is very quiet and a good place to stay. We enjoyed the beach, the athletic club, hiking and snorkeling within walking distance of the home. Kalapaki Joe's is highly recommended for lunch and supper. The feral chickens are delightful. The common are was great for watching a movie in the evening."
United States
Mary M.
The price is NZ$1,195
includes taxes & fees
19 Oct - 20 Oct
🏝 Private Home, Large Lanai -2 Minute Walk to Poipu Beach! 🐠
A beachfront property with a covered patio, outdoor seating, and lush greenery.

18. Beachfront Luxury Home, Panoramic Ocean Views, Walk To Tunnels Beach TVNCU-1214

Beachfront Luxury Home, Panoramic Ocean Views, Walk To Tunnels Beach TVNCU-1214
Hanalei
10.0 out of 10, Exceptional, (118 reviews)
"It was an amazing place!"
United States
Amber M.
The price is NZ$5,935
includes taxes & fees
7 Oct - 8 Oct
Beachfront Luxury Home, Panoramic Ocean Views, Walk To Tunnels Beach TVNCU-1214
A room with a wooden ceiling, a hanging light fixture, a framed picture, and wall-mounted decorative items.

19. Hale Mahealani, Private Treetop Home, Ocean Views

Hale Mahealani, Private Treetop Home, Ocean Views
Princeville
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful time in the Tiki Tower. It was spacious, clean and comfortable. Jess has created a very peaceful and relaxing space. The location provided easy access to both east and west activities. Nearby groceries and restaurants were very convenient. This is an easy recommendation."
United States
Ricardo H.
Hale Mahealani, Private Treetop Home, Ocean Views
A wooden cabinet with a round mirror, two lamps, and a vase with purple flowers.

20. 3BR AC Family Haven with Private Hot Tub

3BR AC Family Haven with Private Hot Tub
Princeville
10.0 out of 10, Exceptional, (4 reviews)
"The house was very comfy and well equipped for our family. The hot tub was especially nice during the wild winter rain storms and cooler evenings. Thanks for the great stay!"
United States
Peter H.
3BR AC Family Haven with Private Hot Tub
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 West Side Hotel Reviews

Koloa Landing Resort at Poipu, Autograph Collection

Koloa Landing Resort at Poipu, Autograph Collection

10/10 Excellent
"Beautiful property! Amazing pool, good margaritas, nice cute coffee shop with snacks and nice fitness center. Loved the location … close to so much!"
Sharon 3-night trip
Posted 1 day ago
Koloa Landing Resort at Poipu, Autograph Collection

Find out more about West Side

West Side Holiday Homes information

Number of reviews
981
Accommodation
553 Holiday Homes
Lowest Price
NZ$836
Highest Price
NZ$5,935

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