Windward Coast Vacation 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 vacation rentals

Luxury Oceanview Punaluu Condo

Luxury Oceanview Punaluu Condo
4.0 star property
Hau`ula
8.2 out of 10, Very good, (29 reviews)
"Nice and cozy place to stay. Smooth communication and easy check-in. Direct access to the beach is also nice. Recommend for people who like relaxing and enjoy local Hawaiian vibes rather than going to town to do some shopping and touristy activities."
United States
Yoshihiro
The price is CA $513
CA $976 total
includes taxes & fees
May 7 - May 8
Luxury Oceanview Punaluu Condo

Oceanfront Vacation Villas at Turtle Bay

Oceanfront Vacation Villas at Turtle Bay
4.5 star property
Kahuku
9.4 out of 10, Exceptional, (117 reviews)
"Wonderful stay! "
United States
David
The price is CA $1,085
CA $1,562 total
includes taxes & fees
Apr 28 - Apr 29
Oceanfront Vacation Villas at Turtle Bay

Kuilima Estates Resort by KBM

Kuilima Estates Resort by KBM
4.0 star property
Kahuku
The price is CA $1,023
CA $1,828 total
includes taxes & fees
May 6 - May 7
Kuilima Estates Resort by KBM

Skyline Island Stay-2 Adjoining Studios

Skyline Island Stay-2 Adjoining Studios
3.0 star property
Waikiki
The price is CA $154
CA $813 total
includes taxes & fees
Apr 21 - Apr 22
Skyline Island Stay-2 Adjoining Studios

Comfy and Modern Condo By Waikiki

Comfy and Modern Condo By Waikiki
3.5 star property
Waikiki
The price is CA $168
CA $829 total
includes taxes & fees
May 11 - May 12
Comfy and Modern Condo By Waikiki

Bishop Suites At The Executive Centre

Bishop Suites At The Executive Centre
4.0 star property
Downtown Honolulu
7.6 out of 10, Good, (105 reviews)
"Clean room and the staff is friendly. "
United States
Cameron
The price is CA $227
CA $311 total
includes taxes & fees
May 3 - May 4
Bishop Suites At The Executive Centre

Island Colony hotel

Island Colony hotel
2.5 star property
Waikiki
The price is CA $213
CA $497 total
includes taxes & fees
Apr 28 - Apr 29
Island Colony hotel

Aston at the Waikiki Banyan

Aston at the Waikiki Banyan
3.0 star property
Waikiki
7.2 out of 10, Good, (2,701 reviews)
"We enjoyed our stay. Nice facilities and close to everything."
United States
Beverly
The price is CA $179
CA $264 total
includes taxes & fees
Apr 19 - Apr 20
Aston at the Waikiki Banyan

Royal Kuhio

Royal Kuhio
3.5 star property
Waikiki
8.6 out of 10, Excellent, (563 reviews)
"Excellent location and the parking was included which was awesome "
United States
Irene
The price is CA $300
CA $356 total
includes taxes & fees
Apr 19 - Apr 20
Royal Kuhio

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, (32 reviews)
"everything was great, I'm sure I'll come to this hotel again"
United States
Nazar
The price is CA $204
CA $589 total
includes taxes & fees
Apr 21 - Apr 22
Partial Ocean View Condo with King or Queen Bed and Parking

@ Marbella Lane -coastal Retreat Near Diamond Head

@ Marbella Lane -coastal Retreat Near Diamond Head
2.5 star property
Diamond Head - Kapahulu - St. Louis
The price is CA $319
CA $619 total
includes taxes & fees
Apr 21 - Apr 22
@ Marbella Lane -coastal Retreat Near Diamond Head

Ilikai Marina Vacations

Ilikai Marina Vacations
3.0 star property
Waikiki
8.4 out of 10, Very good, (39 reviews)
"Clean rooms and spacious, small bathroom but amazing view "
United Kingdom
Neide Katila
The price is CA $167
CA $483 total
includes taxes & fees
May 3 - May 4
Ilikai Marina Vacations

Ala Moana Condo by Zelloo

Ala Moana Condo by Zelloo
3.5 star property
Ala Moana
6.8 out of 10, (97 reviews)
"Room dirty, broken bathroom fixtures. Will not stay here again. "
United States
Ricky Teruo
The price is CA $184
CA $645 total
includes taxes & fees
May 16 - May 17
Ala Moana Condo by Zelloo

Skyline Island Colony Hotel

Skyline Island Colony Hotel
3.0 star property
Waikiki
7.2 out of 10, Good, (2,227 reviews)
"Is a great location "
United States
Emmanuel Rivera
The price is CA $181
CA $255 total
includes taxes & fees
May 3 - May 4
Skyline Island Colony Hotel

Marriott Vacation Club, Waikiki

Marriott Vacation Club, Waikiki
4.0 star property
Waikiki
9.6 out of 10, Exceptional, (155 reviews)
"Room and staff wete incredible - would book again!"
Canada
Michael
The price is CA $448
CA $532 total
includes taxes & fees
Apr 19 - Apr 20
Marriott Vacation Club, Waikiki

Tropical Studios at Marine Surf Waikiki

Tropical Studios at Marine Surf Waikiki
3.0 star property
Waikiki
8.4 out of 10, Very good, (372 reviews)
"The staff was amazing The place was very clean And the location was excellent "
United States
Lawrence Thomas
The price is CA $167
CA $362 total
includes taxes & fees
Apr 19 - Apr 20
Tropical Studios at Marine Surf Waikiki

Regency on Beachwalk Waikiki by OUTRIGGER

Regency on Beachwalk Waikiki by OUTRIGGER
3.5 star property
Waikiki
8.2 out of 10, Very good, (447 reviews)
"Room was clean, great central location and staff was excellent. "
Canada
kerry
The price is CA $370
CA $1,005 total
includes taxes & fees
Apr 18 - Apr 19
Regency on Beachwalk Waikiki by OUTRIGGER

Aston Waikiki Sunset

Aston Waikiki Sunset
4.0 star property
Waikiki
7.8 out of 10, Good, (3,187 reviews)
"Great and convenient location but the hotel is old and outdated."
United States
Faye
The price is CA $220
CA $318 total
includes taxes & fees
Apr 30 - May 1
Aston Waikiki Sunset

Palms at Waikiki by Tropical Escapes

Palms at Waikiki by Tropical Escapes
3.0 star property
Waikiki
7.8 out of 10, Good, (13 reviews)
"It is located in a great area."
United States
Leonard Frank
The price is CA $173
CA $619 total
includes taxes & fees
Apr 24 - Apr 25
Palms at Waikiki by Tropical Escapes

Diamond Head and Partial Ocean views with 2 Beds and Parking

Diamond Head and Partial Ocean views with 2 Beds and Parking
3.5 star property
Waikiki
9.4 out of 10, Exceptional, (37 reviews)
"An amazing place to stay. Location parking and communication was beyond our expectations Loved it so much!!! We will definitely be back "
United States
Rodolfo
The price is CA $271
CA $679 total
includes taxes & fees
Apr 28 - Apr 29
Diamond Head and Partial Ocean views with 2 Beds and Parking
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 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.