A coastal landscape with a mountain range, a town, and a clear blue sea.

Windward Coast Vacation Rentals

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Our top choices for Windward Coast vacation rentals

1. Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,282 reviews)
"It was a pleasant stay… I’m definitely coming back."
United States
andrea
The price is CA $233
CA $334 total
includes taxes & fees
Oct 13 - Oct 14
Aston Waikiki Sunset

2. Luxury Beachfront Condo with View

Luxury Beachfront Condo with View
Hauula
9.6 out of 10, Exceptional, (103 reviews)
"Ideal location for island exploring and an amazing view for evenings and early mornings. We had two young kids and the stay was perfect for a family of 4. Even though the building was undergoing renovations during the stay, the disruption was minimal for our unit."
United States
Dale S.
The price is CA $323
CA $1,028 total
includes taxes & fees
Sep 24 - Sep 25
Luxury Beachfront Condo with View

3. Diamond Head and Ocean views with King Bed and Parking

Diamond Head and Ocean views with King Bed and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (21 reviews)
"Very close to the beach. Amenities like the sauna were really nice"
United States
John
The price is CA $226
CA $651 total
includes taxes & fees
Sep 24 - Sep 25
Diamond Head and Ocean views with King Bed and Parking

4. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,298 reviews)
"Clean room, friendly staff, good location near the beach"
United States
Fernando
The price is CA $156
CA $244 total
includes taxes & fees
Sep 30 - Oct 1
Skyline Island Colony Hotel

5. NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio

NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio
Waikiki
9.4 out of 10, Exceptional, (77 reviews)
"Stayed here for 20 days. Great location and a block away from the beach."
United States
Arpita B.
The price is CA $123
CA $685 total
includes taxes & fees
Sep 26 - Sep 27
NEW Fall Deal Walk to Waikiki Beach from a Cool City Studio

6. Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop

Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop
Waikiki
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful place and wonderful host! Will come again."
United States
AVenture
The price is CA $72
CA $385 total
includes taxes & fees
Oct 21 - Oct 22
Cozy condo at Hawaiian monarch- no resort fee, free parking, near beaches, shop

7. Tropical Studios at Marine Surf Waikiki

Tropical Studios at Marine Surf Waikiki
3.0 star property
Waikiki
8.4 out of 10, Very good, (378 reviews)
"Perfect location. View from the balcony was amazing. Bed mattress could be updated."
United States
Alejandro Ray
The price is CA $152
CA $347 total
includes taxes & fees
Oct 5 - Oct 6
Tropical Studios at Marine Surf Waikiki

8. Beachfront Condo with Beach Access & Pool

Beachfront Condo with Beach Access & Pool
Hauula
9.4 out of 10, Exceptional, (44 reviews)
"Great communication. Super clean! Construction didn’t impact us at all. The view is absolutely beautiful! We would not hesitate to book this unit again! "
United States
Julie C.
The price is CA $347
CA $1,074 total
includes taxes & fees
Oct 16 - Oct 17
Beachfront Condo with Beach Access & Pool

9. Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi
Waikiki
9.0 out of 10, Wonderful, (135 reviews)
"Really convenient location, a beautiful view, comfortable amenities. Pleasant and helpful communication with host."
United States
April B.
The price is CA $127
CA $354 total
includes taxes & fees
Sep 24 - Sep 25
Charming Studio in Waikiki - 2 Full size Beds, Free Wi-Fi

10. Waikiki renovated modern studio

Waikiki renovated modern studio
Waikiki
9.2 out of 10, Wonderful, (115 reviews)
"I like everything about this hotel 💯"
United States
Kreta
The price is CA $115
CA $292 total
includes taxes & fees
Sep 27 - Sep 28
Waikiki renovated modern studio

11. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.4 out of 10, Good, (2,769 reviews)
"The check in was easy and they even let us check in a few hours early when we only meant to drop off luggage. Room was clean and large- a little older style but roomy with great view.parking was plentiful. Great location to everything. The people at desk and parking were so nice. Have stayed there before will return!"
United States
Jocelyn
The price is CA $233
CA $329 total
includes taxes & fees
Oct 13 - Oct 14
Aston at the Waikiki Banyan

12. Awesome view. Walking distance to beach, restaurants, shopping

Awesome view. Walking distance to beach, restaurants, shopping
Waikiki
9.4 out of 10, Exceptional, (32 reviews)
"Great location and view"
United States
Tarin K.
The price is CA $135
CA $399 total
includes taxes & fees
Sep 28 - Sep 29
Awesome view. Walking distance to beach, restaurants, shopping

13. Partial Ocean View Condo with King or Queen Bed and Parking

Partial Ocean View Condo with King or Queen Bed and Parking
3.5 star property
Waikiki
9.6 out of 10, Exceptional, (42 reviews)
"Overall everything was great the property is next to the shopping center and store"
United States
Jessy
The price is CA $279
CA $713 total
includes taxes & fees
Oct 13 - Oct 14
Partial Ocean View Condo with King or Queen Bed and Parking

14. King Bed • Renovated • Canal & Mountain View • Walk to Beach

King Bed • Renovated • Canal & Mountain View • Walk to Beach
Waikiki
9.6 out of 10, Exceptional, (66 reviews)
"Clean space, great location, very responsive host. Would gladly stay here again!"
United States
Emily K.
The price is CA $143
CA $426 total
includes taxes & fees
Sep 27 - Sep 28
King Bed • Renovated • Canal & Mountain View • Walk to Beach

15. Soothing Hawaii Condo - 18th FL

Soothing Hawaii Condo - 18th FL
Waikiki
9.2 out of 10, Wonderful, (78 reviews)
"Great location"
United States
Jacki M.
The price is CA $119
CA $342 total
includes taxes & fees
Sep 26 - Sep 27
Soothing Hawaii Condo - 18th FL

16. @ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel

@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel
Diamond Head - Kapahulu - St. Louis
9.4 out of 10, Exceptional, (64 reviews)
"Great location around diamond head area, close to regional park."
United States
Weijuan
The price is CA $190
CA $452 total
includes taxes & fees
Sep 25 - Sep 26
@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel

17. Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (628 reviews)
"The location was great, it’s within walking distance to every thing."
United States
MARIA ISABEL
The price is CA $350
CA $415 total
includes taxes & fees
Oct 20 - Oct 21
Royal Kuhio

18. Charming cozy condo in marvelous Honolulu with WiFi

Charming cozy condo in marvelous Honolulu with WiFi
Waikiki
9.8 out of 10, Exceptional, (58 reviews)
"Great stay, wish we were staying longer!"
United States
Mariah H.
The price is CA $125
CA $346 total
includes taxes & fees
Sep 30 - Oct 1
Charming cozy condo in marvelous Honolulu with WiFi

19. "Hina Hideaway", Views, A/C, ~5 min Walk to Beach

"Hina Hideaway", Views, A/C, ~5 min Walk to Beach
Punaluu
10.0 out of 10, Exceptional, (53 reviews)
"Perfect place to visit North Shore. Close to lots of great things to do. Perfect view of ocean. "
United States
David P.
The price is CA $394
CA $986 total
includes taxes & fees
Sep 28 - Sep 29
"Hina Hideaway", Views, A/C, ~5 min Walk to Beach

20. Spacious Condo on Turtle Bay Golf Course

Spacious Condo on Turtle Bay Golf Course
Kahuku
9.6 out of 10, Exceptional, (22 reviews)
"Perfect condo for 2 people, very clean & well stocked; great location; will definitely rebook for a future visit. "
United States
Carolyn T.
The price is CA $288
CA $755 total
includes taxes & fees
Sep 30 - Oct 1
Spacious Condo on Turtle Bay Golf Course
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 Windward Coast Hotel Reviews

Find out more about Windward Coast

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windward Coast. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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