Holiday Rentals in Leeward Coast

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Leeward Coast

Our top choices for Leeward Coast holiday rentals

Hawaiian Princess at Makaha Beach

3.5 star property
8.8 out of 10, Excellent, (70)
"Great private beach and views"
Hawaiian Princess at Makaha Beach

SURFERS DREAM STUDIO

9.4 out of 10, Exceptional, (194)
"Had everything we needed plus more. The private balcony/deck was a bonus. Great hospitality by the hosts! We will definitely be back!"
SURFERS DREAM STUDIO

Cozy Beach front condo in Makaha

9.6 out of 10, Exceptional, (161)
"Such a great place to stay. Far away from town which is great. We wanted somewhere private and quiet. Oahu was small enough we get to drive everywhere, everyday. The private beach was a huge plus. Practically having the whole beach to ourselves. The property was amazing and we thoroughly enjoyed our stay!"
Cozy Beach front condo in Makaha

Charming Studio Apartment with Cold AC in fabulous Makaha

9.6 out of 10, Exceptional, (5)
The price is €285
includes taxes & fees
3 Sept - 4 Sept
Charming Studio Apartment with Cold AC in fabulous Makaha

The Beach Villas at Ko Olina by Real Select Vacations

4.0 star property
9.8 out of 10, Exceptional, (70)
"Beautiful location "
The Beach Villas at Ko Olina by Real Select Vacations

Ocean View Home for Family Fun Getaway Near Beach w/Hot Tub and Bbq Grill

9.2 out of 10, Wonderful, (15)
"This gem has the perfect view of the sky and overlooking the ocean! Safe and quiet with plenty of room to spare."
Ocean View Home for Family Fun Getaway Near Beach w/Hot Tub and Bbq Grill

First Class Luxury Beach Front Resort Condominium

10.0 out of 10, Exceptional, (165)
"Absolutely beautiful property! We lived in the area several years ago and love going back to Ko Olina any opportunity we get. "
First Class Luxury Beach Front Resort Condominium

Luxury Ko Olina Beach Villa with Ocean View 2BR 2BA in Beach Tower

10.0 out of 10, Exceptional, (142)
"We’ve stayed at this property before in a different unit. Both times had an amazing stay, but the location of this particular unit gave us a stunning ocean view. Really couldn’t be happier with our experience and we will definitely be back to stay again."
Luxury Ko Olina Beach Villa with Ocean View 2BR 2BA in Beach Tower

Beach Villas at Ko Olina Premium Corner Penthouse Villa Spectacular Ocean views

10.0 out of 10, Exceptional, (151)
"Great property, great location, great sunset view! Awesome selection of family items…from a wagon to strollers, high chairs, sand toys, beach chairs…this condo is amazing. Very responsive owner and management company. Highly recommended!! "
Beach Villas at Ko Olina Premium Corner Penthouse Villa Spectacular Ocean views

Luxury Oceanview Villa at Beach Villas at Ko Olina Resort

9.8 out of 10, Exceptional, (161)
"We had a wonderful trip and the accommodations were perfect for 2 adults and 2 children. We hope to be back again!"
Luxury Oceanview Villa at Beach Villas at Ko Olina Resort

Beach Front Condo - Makaha

9.8 out of 10, Exceptional, (11)
"Place was great"
Beach Front Condo - Makaha

Gorgeous Beach Front Home with Amazing Sunsets

10.0 out of 10, Exceptional, (79)
"This house was great to stay in. We wanted freedom of movement. The shopping was so good and you are away from the noise. Will definitely in the future stay with Reyna again. The view from the backyard was truly amazing. And our host, also amazing. Thanks."
Gorgeous Beach Front Home with Amazing Sunsets

Marriott's Ko Olina Beach Club, Kapolei, Stunning Studio

9.4 out of 10, Exceptional, (45)
"Relaxing, just a great place"
Marriott's Ko Olina Beach Club, Kapolei, Stunning Studio

25% Off Aug 21–Sept 17, 2025! Luxurious Penthouse—Ocean, Beach & Pool Views!

10.0 out of 10, Exceptional, (123)
"Incredible ocean views, with a true relaxing aloha lifestyle, "
25% Off Aug 21–Sept 17, 2025! Luxurious Penthouse—Ocean, Beach & Pool Views!

Ocean View Home Near the Beach and the Golf Course in Secure Gated Community

9.8 out of 10, Exceptional, (28)
"Very comfortable and clean home. Really enjoyed the night market at the golf course (it takes place only once a month and we were lucky). "
Ocean View Home Near the Beach and the Golf Course in Secure Gated Community

Hawaiian Princess 206 90/TVU-0075

8.0 out of 10, Very good, (52)
"Beautiful view and beach, dated accommodations but comfortable. Bed was comfortable and we appreciated the beach chairs and misc condiments in the kitchen. Homeless encampments on the way were larger than expected but they were not on beach by the unit. "
Hawaiian Princess 206 90/TVU-0075

SALE Oct-Dec! Upgraded BeachFront Ocean View 3-BR 2.5BA Villa 1734 sq.ft Floor 7

10.0 out of 10, Exceptional, (196)
"Great stay for large Families "
SALE Oct-Dec! Upgraded BeachFront Ocean View 3-BR 2.5BA Villa 1734 sq.ft Floor 7

2 Side x Side Villas - 3br + 2br on Same Floor-Sleeps up to 14! Great for Groups

9.8 out of 10, Exceptional, (26)
"Very clean, beautiful and comfortable setting for celebrating my Parent’s 60th with all children and spouses. Views of the ocean from balcony and perfect pools and sandy beach right below. Perfect, convenient location to see all the sites as well. We loved our time here."
2 Side x Side Villas - 3br + 2br on Same Floor-Sleeps up to 14! Great for Groups

Family Friendly, Fully Furnished Villa In Ko Olina Resort near the Golf Course

9.6 out of 10, Exceptional, (37)
"We loved our stay. The property is great. Location is just what we wanted. Central to everything but not busy."
Family Friendly, Fully Furnished Villa In Ko Olina Resort near the Golf Course

Elite Condo with Spectacular VIEWS ❤️

7.8 out of 10, Good, (87)
"We enjoyed our stay, great views. Great value for Oahu. Communication was excellent with the host!"
Elite Condo with Spectacular VIEWS ❤️
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 Leeward Coast Hotel Reviews

Find out more about Leeward Coast

Find out more about Leeward Coast

Everything you need to know about Leeward Coast holiday rentals

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

Leeward Coast holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leeward 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 Leeward Coast holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leeward Coast holiday rentals we have selected for you start as low as €285 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Leeward Coast rentals

At Expedia, we put the best Leeward Coast holiday 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 Leeward 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 Leeward Coast holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leeward 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.