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

Windward Coast Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windward Coast holiday rentals

1. Marriott Vacation Club, Waikiki

Marriott Vacation Club, Waikiki
4.0 star property
Waikiki
9.6 out of 10, Exceptional, (184 reviews)
"Convenient walk to the beach, respectful guests throughout, clean space and amazing view from the pool!"
United States
Eliza Mikiye Kawazoye
The price is NZ$656
includes taxes & fees
31 Aug - 1 Sept
Marriott Vacation Club, Waikiki

2. Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,267 reviews)
"It was great stay very convenient close to the beach and everything at short walking distance."
United States
Daniel
The price is NZ$419
includes taxes & fees
20 Sept - 21 Sept
Aston Waikiki Sunset

3. Oceanfront Vacation Villas at Turtle Bay

Oceanfront Vacation Villas at Turtle Bay
4.5 star property
Kahuku
9.4 out of 10, Exceptional, (118 reviews)
"A perfect day at Turtle Bay Resort."
United States
Renee
The price is NZ$1,668
includes taxes & fees
30 Aug - 31 Aug
Oceanfront Vacation Villas at Turtle Bay

4. 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, (41 reviews)
"Overall experience was great free parking walking distance to the beach plenty of places to keep busy 👍"
United States
Erwin
The price is NZ$829
includes taxes & fees
1 Sept - 2 Sept
Partial Ocean View Condo with King or Queen Bed and Parking

5. Marriott's Ko'Olina Beach Club

Marriott's Ko'Olina Beach Club
4.0 star property
Ko Olina
8.8 out of 10, Excellent, (1,018 reviews)
"Room was very clean and the food was excellent. Staff was extremely friendly and helpful"
United States
Carole
The price is NZ$1,026
includes taxes & fees
11 Sept - 12 Sept
Marriott's Ko'Olina Beach Club

6. Regency on Beachwalk Waikiki by OUTRIGGER

Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
Waikiki
8.4 out of 10, Very good, (478 reviews)
"Great room, friendly staff and great location"
United States
Julian
The price is NZ$1,269
includes taxes & fees
27 Sept - 28 Sept
Regency on Beachwalk Waikiki by OUTRIGGER

7. Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,292 reviews)
"This place was so good"
United States
Tae
The price is NZ$309
includes taxes & fees
31 Aug - 1 Sept
Skyline Island Colony Hotel

8. Panoramic Oceanview Resort

Panoramic Oceanview Resort
4.0 star property
Waikiki
9.0 out of 10, Wonderful, (28 reviews)
"The Panaramic Ocean View Resort was a great choice! Absolutely wonderful place to stay. It's a great location with a great view. Lots to do within walking distance. The room was spacious with all you need. Our nine nights were incredible!"
United States
John
The price is NZ$1,178
includes taxes & fees
27 Sept - 28 Sept
Panoramic Oceanview Resort

9. Aulani, Disney Vacation Club Villas

Aulani, Disney Vacation Club Villas
5.0 star property
Ko Olina
8.8 out of 10, Excellent, (1,015 reviews)
"This is an amazing property that is very clean and family friendly!!"
United States
Brian
The price is NZ$1,314
includes taxes & fees
31 Aug - 1 Sept
Aulani, Disney Vacation Club Villas

10. Beachfront Penthouse w/ 3 Lanais on O’ahu!

Beachfront Penthouse w/ 3 Lanais on O’ahu!
Hauula
9.4 out of 10, Exceptional, (111 reviews)
"The condo was just as described! Fantastic views"
United States
Julie D.
The price is NZ$2,392
includes taxes & fees
1 Sept - 2 Sept
Beachfront Penthouse w/ 3 Lanais on O’ahu!

11. "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, (56 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 NZ$1,171
includes taxes & fees
1 Sept - 2 Sept
"Hina Hideaway", Views, A/C, ~5 min Walk to Beach

12. Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.2 out of 10, Good, (2,758 reviews)
"Excellent hotel."
United States
Alisher
The price is NZ$376
includes taxes & fees
31 Aug - 1 Sept
Aston at the Waikiki Banyan

13. Rarely Available! Romantic Honeymoon Villa 120

Rarely Available! Romantic Honeymoon Villa 120
Kahuku
10.0 out of 10, Exceptional, (126 reviews)
"Amazing property! Perfect location and amenities. Will definitely be staying again. "
United States
Megan
The price is NZ$2,311
includes taxes & fees
27 Sept - 28 Sept
Rarely Available! Romantic Honeymoon Villa 120

14. Premium Remodeled Condo with Ocean View and Parking

Premium Remodeled Condo with Ocean View and Parking
4.0 star property
Waikiki
9.4 out of 10, Exceptional, (39 reviews)
"Very relaxing and great location!"
United States
David
The price is NZ$903
includes taxes & fees
30 Aug - 31 Aug
Premium Remodeled Condo with Ocean View and Parking

15. Extraordinary Listing on the Block! 2 Story Condo Renovated!

Extraordinary Listing on the Block! 2 Story Condo Renovated!
Kahuku
9.6 out of 10, Exceptional, (302 reviews)
"We loved our stay and would definitely book again! The beds were so comfortable and the location was amazing!"
United States
chris m.
The price is NZ$1,594
includes taxes & fees
1 Sept - 2 Sept
Extraordinary Listing on the Block! 2 Story Condo Renovated!

16. Waikiki Shore by OUTRIGGER

Waikiki Shore by OUTRIGGER
3.0 star property
Waikiki
8.4 out of 10, Very good, (601 reviews)
"Room 614. Good location with a view of the water, as the accommodation is on the beachfront. Room had its own washer and dryer, which was fantastic. Close to everything."
Australia
Michael James
The price is NZ$1,202
includes taxes & fees
1 Sept - 2 Sept
Waikiki Shore by OUTRIGGER

17. Luxury townhouse on Turtle Bay golf course near the ocean

Luxury townhouse on Turtle Bay golf course near the ocean
Kahuku
9.8 out of 10, Exceptional, (230 reviews)
"Enjoyed the stay"
United States
Stephanie G.
The price is NZ$1,285
includes taxes & fees
30 Aug - 31 Aug
Luxury townhouse on Turtle Bay golf course near the ocean

18. New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!

New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!
Waikiki
9.4 out of 10, Exceptional, (205 reviews)
"This was a beautiful and really clean condo! The view was gorgeous. Front row to amazing sunsets and the Friday night fireworks. The bed was so, so comfortable, and I slept so soundly. The host was really nice and communicated well with us. Highly recommend this place! "
United States
Lori C.
The price is NZ$836
includes taxes & fees
30 Aug - 31 Aug
New Decor! Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row, FAB!

19. NEW North Shore Oahu: Turtle Bay 1 bedroom plus 1 loft bedroom

NEW North Shore Oahu: Turtle Bay 1 bedroom plus 1 loft bedroom
Kahuku
9.8 out of 10, Exceptional, (20 reviews)
"The place was very comfortable, had easy access to Turtle Bay beaches, and was a good base camp for North Shore adventures."
United States
Michelle C.
NEW North Shore Oahu: Turtle Bay 1 bedroom plus 1 loft bedroom

20. Spacious 1 Bedroom Condo at Turtle Bay

Spacious 1 Bedroom Condo at Turtle Bay
Kahuku
9.6 out of 10, Exceptional, (44 reviews)
"We spent 5 days at the condo and enjoyed every minute. Helena was extremely helpful and the property was as advertised."
United States
William K.
The price is NZ$928
includes taxes & fees
9 Sept - 10 Sept
Spacious 1 Bedroom Condo at Turtle Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windward Coast Hotel Reviews

Find out more about Windward Coast

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windward Coast holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windward Coast. 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 Windward Coast. 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 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 holiday 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 Windward Coast short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia