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Leeward Coast Vacation Rentals

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Our top choices for Leeward Coast vacation rentals

7.8 out of 10, Good, (148)
"Our stay at the condo was 10/10! The condo has all the basics you need for a comfortable stay. The views and landscape were stunning, the condo was nicely updated and clean, and the bed was comfortable! The property is very secure, quiet, and although older is meticulously maintained. We were a bit worried about the area after reading reviews online, but everyone was friendly and we felt very safe touring around, going to the beach, and local businesses. After spending 5 nights in Waikiki, the...
Canada
Jennifer
$230 nightly
The price is $268
Dec 20 - Dec 21
Total with taxes and fees
Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!
9.8 out of 10, Exceptional, (13)
"This condo is a beautiful slice of paradise in the most beautiful and peaceful spot on Oahu. I stayed during the 4th of July and didn’t hear a single firework due to the quiet solitude. Vanessa, the owner, is a very responsive and helpful host, and I highly recommend this spot."
United States
Luke A.
$313 nightly
The price is $364
Dec 21 - Dec 22
Total with taxes and fees
Charming Studio Apartment with Cold AC in fabulous Makaha
10.0 out of 10, Exceptional, (1)
"The location is quiet and private. It is well decorated and had everything we needed, plus things we didn't know we needed...like beach towels, beach chairs and beach gear."
United States
Blaine J.
$400 nightly
The price is $468
Jan 5 - Jan 6, 2026
Total with taxes and fees
Studio Nene - Beaches, King Bed, Mountains
7.8 out of 10, Good, (99)
"We enjoyed our stay, great views. Great value for Oahu. Communication was excellent with the host!"
United States
Peggy
$286 nightly
The price is $334
Jan 13 - Jan 14, 2026
Total with taxes and fees
Elite Condo with Spectacular VIEWS ❤️
9.8 out of 10, Exceptional, (154)
"Stunning views! "
United States
Mary Michael S.
$482 nightly
The price is $561
Dec 27 - Dec 28
Total with taxes and fees
SERENDIPITY ON THE MOANA - Legal & Oceanfront - Great for Work & Play!
10.0 out of 10, Exceptional, (11)
"The property has beautiful views, it was peaceful, quite and in gated community. The house was clean and more than enough room for my family. They had games that you could play as a family. I highly recommend this property for anyone that i a looking for a relaxing vacation. "
United States
tasha
$1,753 nightly
The price is $2,047
Dec 30 - Dec 31
Total with taxes and fees
4 Bdrm, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

Apartment in Waianae

Studio- Ocean View Hideaway
2.0 star property
10.0 out of 10, Exceptional, (1)
"I wish I had rented this for the week. It was great. f I return to Oahu I will check here first. "
United States
Stephen M.
$444 nightly
The price is $521
Jan 6 - Jan 7, 2026
Total with taxes and fees
Studio- Ocean View Hideaway
10.0 out of 10, Exceptional, (3)
"The views are amazing! We went to my daughter’s wedding on the other side of the island and it was perfect!Evenings in the hot tub were perfect!A short walk and we could swim in a pool. This is a beautiful home with a back yard we could have meals in and spend time with each other! "
United States
Sandy W.
$2,064 nightly
The price is $2,404
Dec 31 - Jan 1, 2026
Total with taxes and fees
Family Oceanview Oasis, Hot Tub, Sleep 12

Vacation Home in Waianae

Kalo Homes ~ Mauka to Makai
10.0 out of 10, Exceptional, (4)
"We were very impressed with the place, it was very clean and bright. We especially love that there were clean sponges to wash dishes with! The host was fabulous and responsive with communication. Thank you for a wonderful place to stay for our vacation, looking forward to staying here again in the future!"
Canada
Jessica K.
$1,043 nightly
The price is $1,221
Jan 5 - Jan 6, 2026
Total with taxes and fees
Kalo Homes ~ Mauka to Makai
2.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect Hawaiian Getaway!This home is a true paradise—clean, spacious, and beautifully maintained. The open layout, natural light, and ocean breezes make it incredibly relaxing. Conveniently located near beaches, restaurants, and attractions, it’s the ideal spot for a dream Hawaiian vacation!"
United States
Gaspard Van K.
$1,119 nightly
The price is $1,310
Jan 7 - Jan 8, 2026
Total with taxes and fees
Oahu Family cabin_Oceanview and Beach Fun
10.0 out of 10, Exceptional, (19)
"Wonderful family stay in a perfect location!"
United States
Angela C.
$963 nightly
The price is $1,120
Dec 19 - Dec 20
Total with taxes and fees
★Oahu Perfect Vacation • Million Dollar Views, Pool, Near Beach, 4BR Sleeps 14★
10.0 out of 10, Exceptional, (5)
"We had a great time on this property. It was clean, spacious, and the owners were very good at responding in a timely matter. My family of 6 and I would definitely stay here again. "
United States
Claudia S.
$1,024 nightly
The price is $1,196
Jan 13 - Jan 14, 2026
Total with taxes and fees
4 beds, Near Beach, Pool, Spa, Gym, Ocean Views
10.0 out of 10, Exceptional, (2)
"Very accommodating property and host"
United States
Mike S.
$1,538 nightly
The price is $1,796
Dec 21 - Dec 22
Total with taxes and fees
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ
10.0 out of 10, Exceptional, (1)
$1,363 nightly
The price is $1,595
Dec 21 - Dec 22
Total with taxes and fees
3 Bdrm, Near Beach, Sngl LVL, Pool/Spa, Gym, BBQ
10.0 out of 10, Exceptional, (6)
"Overall a great place to stay. While we were there to work, being able to walk up to the Kane'aki Heiau just up the hill was an extra treat."
United States
Robin B.
$1,341 nightly
The price is $1,567
Jan 2 - Jan 3, 2026
Total with taxes and fees
3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym
$1,146 nightly
The price is $1,338
Jan 11 - Jan 12, 2026
Total with taxes and fees
Kalo Homes - Makaha Mountain Hideaway
$1,672 nightly
The price is $1,954
Jan 3 - Jan 4, 2026
Total with taxes and fees
New 4 Bedroom, Amazing Views, Near Beach, Free prk
7.6 out of 10, Good, (4)
"Our family really enjoyed out stay at Marriott Beach Club and plan to return again. Host was awesome along with communication. Worth it in every way!!!"
United States
Kathy J.
$1,738 nightly
The price is $1,746
Jan 12 - Jan 13, 2026
Total with taxes and fees
Marriott's Ko Olina Beach Club (3BR)
9.6 out of 10, Exceptional, (93)
"Relaxing, just a great place"
United States
ANTHONY
$816 nightly
The price is $847
Jan 2 - Jan 3, 2026
Total with taxes and fees
Marriotts Ko Olina Beach Club - Studio
9.8 out of 10, Exceptional, (14)
"The resort is very well maintained, has a great protected beach area and good amenities. The unit is spacious, comfortable and stocked with everything you need. "
United States
Scott M.
$1,352 nightly
The price is $1,407
Dec 26 - Dec 27
Total with taxes and fees
Marriotts Ko Olina Beach Club - 1 Bedroom
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 Leeward Coast Hotel Reviews

Find out more about Leeward Coast

Everything you need to know about Leeward 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 Leeward Coast vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leeward Coast vacation 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 low season months. For more hustle and bustle, you may prefer to visit Leeward Coast in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $268 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leeward Coast rentals

At Expedia, we put the best Leeward 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 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 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 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.