Windward Coast Vacation Rentals from CA $211: Short-Term Rentals for 2026

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Our top choices for Windward Coast vacation rentals

1. Luxurious five-bedroom modern retreat

Enchanted Lake

Wytske K.

CA $3,288 total

includes taxes & fees

Oct 19 - Oct 20

A coastal cityscape with a beach, high-rise buildings, and a clear view of the ocean.

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

Waikiki

Jessy

CA $677 total

includes taxes & fees

Oct 25 - Oct 26

A nighttime cityscape with a prominent high-rise building reflecting on the water.

3. Waikiki renovated modern studio

Waikiki

Cindy

CA $297 total

includes taxes & fees

Nov 13 - Nov 14

A modern kitchen with a large window, a flat-screen TV, and a dining area with a table set for two.

4. Newly Renovated · Ocean View Corner Studio · King Bed · Walk to Beach

Waikiki

Robert A.

CA $396 total

includes taxes & fees

Oct 23 - Oct 24

A building with a sign reading "KUHIO VILLAGE TOWER 2463".

5. Aloha Suite Near the Sea III - 2 Block Walk to Beach!

Waikiki

Sarah

CA $422 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a bed, a nightstand, a lamp, a balcony with a table and chairs, and a city view.

6. Skyline Island Colony Hotel

Waikiki

Iurii

CA $211 total

includes taxes & fees

Nov 16 - Nov 17

A bar area with a view of the ocean and palm trees, featuring bar stools and a wine glass rack.

7. Closest to Beach, Ritz-Carlton & Lush Trails - Steps from Pool & Grill

Kahuku

"Jill was a wonderful host. The rental was perfect for the first few nights of our honeymoon. We were both feeling tired and under the weather after our wedding and it ended up being the perfect place to decompress and get some read before heading to honolulu for the rest of our trip. Jill left great directions and and great north shore tips for us! We really enjoyed spending time on the lanai watching all the birds. Would definitely stay again!"

Paige

CA $868 total

includes taxes & fees

Oct 24 - Oct 25

A sunset over the ocean with rocky shorelines and trees framing the view.

8. Comfortable Condo on Turtle Bay Golf Course Sleeps 5

Kahuku

Andrea

CA $825 total

includes taxes & fees

Nov 3 - Nov 4

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Top Windward Coast Hotel Reviews

Holiday Inn Express Waikiki by IHG

8/10 Good

"El servicio fue bueno los trabajadores muy atentos y me gustó la zona donde está el Hotel"

Sheraton Waikiki Beach Resort

8/10 Good

"Convenient location, great view. Food was ok. Reserved a king room, when I checked in, they said they’re all gone, all they had was 2 doubles. Then maintenance came to our room, said they had a bad outlet, asked to close the door to our lanai (we wanted the fresh air) he tapped all the outlets with his finger, said they’re “ok.” I’ve been an electrician for 26 years, never seen that before."

Halepuna Waikiki by Halekulani

8/10 Good

"Staff (mostly the bellmen/valet) was very friendly and helpful. The property overall looks great and is well maintained. The room is very simple, but I find that to be true of most rooms in Waikiki. It was clean and the view was amazing. My only issue was the noise bleeding through from the other rooms. I could hear whole conversations from the people next to me, but I was more bothered by the noise from wherever was happening above me. Constant noise and at one point running some kind of machine that sounded like they were drilling into the floor. Otherwise good stay."

'Alohilani Resort Waikiki Beach

10/10 Excellent

"The hotel is beautiful and clean, nice rooftop bar and pool. I enjoyed the infinity like pool. We had the king sized, diamondhead, beach view room with balcony. Room and bathroom were spacious. The hotel concierge desk is very helpful. You get to rent 3 beach rentals at no cost. We got 2 chairs and an umbrella. Parking is expensive if you get a rental car, but one isn't needed. I’d definitely stay here again."

Waikiki Resort Hotel

8/10 Good

"The room was nice but the shower was a little small (would recommend to get rid of the tub and do a ceramic shower only) the fitness room needs AC (too hot in there) and it's too small and can only accommodate 2 people. The treadmill didn't work. The complimentary breakfast was excellent and the host were also very friendly and polite. We liked the location, being so close to Waikiki beach, shopping plaza and many great restaurants. The pool water was too cold to use, I would recommend heating so that guest can use it even if it's not great weather or in the evening. Overall I think we paid a little too much for our stay but it was comfortable and in a great location"

Hilton Waikiki Beach Resort & Spa

8/10 Good

"We stayed at the Hilton Waikiki Resort & Spa for 9 nights in October. We were happy to get a good deal given our trip was in October. Overall, our interactions with the staff including housekeeping, front desk, valet, and staff responding to text messages were all very positive and helpful. Everyone offered to help promptly. We had a room with a beautiful ocean view from the 35th floor. For a Hilton, I think that the furniture in the room could have been in better condition such as the main cabinet in the guest room. The closet was in the bathroom which made getting clothes in and out a bit more tricky given it is tight near the bathroom entrance. If there were more hooks on the wall to hang up towels or clothes, that would have been very helpful given that surface space to put stuff down on was also limited. We didn't have time to use the pool and hot tub during our stay, but the deck was beautiful especially at night with the fire pits. We did enjoy having mini golf on the deck. We used the gym a few times and found it to be well-equipped. Tip: the water from the water bottle filler in the gym is the coldest compared to the one on the main floor and 10th floor (on the deck). It was wonderful to be able to refill our water bottles and not waste water bottles. It would have been nice to have a separate recycling bin in the guestroom. On the 9th floor, there is a microwave and laundry facilities which was very helpful. Overall, I would stay here again if there was a good deal"

Find out more about Windward Coast

Everything you need to know about Windward Coast vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Coast vacation rental for you. At Expedia, you can take your pick from private vacation 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 Windward Coast vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Coast vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Coast. 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 Windward Coast vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windward Coast vacation rentals we have selected for you start as low as CA $211 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windward Coast rentals

At Expedia, we put the best Windward Coast vacation 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 Windward Coast 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 Windward Coast vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windward Coast. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Windward Coast Vacation Rentals

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Our top choices for Windward Coast vacation rentals

1. Luxurious five-bedroom modern retreat

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

3. Waikiki renovated modern studio

4. Newly Renovated · Ocean View Corner Studio · King Bed · Walk to Beach

5. Aloha Suite Near the Sea III - 2 Block Walk to Beach!

6. Skyline Island Colony Hotel

7. Closest to Beach, Ritz-Carlton & Lush Trails - Steps from Pool & Grill

8. Comfortable Condo on Turtle Bay Golf Course Sleeps 5

9. NEW! RusticLuxe — Fully Custom Boss Cabin at Turtle Bay

10. Delux, spacious, clean condo with AC, WIFI, pool, golf course, near famous beach

11. Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

12. Diamond Head and Partial Ocean views with 2 Beds and Parking

13. Elite Condo with Spectacular VIEWS ❤️

14. Charming Studio Apartment with Cold AC in fabulous Makaha

15. Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!

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

17. Charming cozy condo in marvelous Honolulu with WiFi

18. Aston Waikiki Sunset

19. Relaxing Ocean View Boutique Condo - 20th FL

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

Find vacation rentals that suit your style

Top Windward Coast Hotel Reviews

Holiday Inn Express Waikiki by IHG

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