Leeward Coast Vacation Rentals

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Our top choices for Leeward Coast vacation rentals

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

Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!
Waianae
7.8 out of 10, Good, (151 reviews)
"I had an amazing stay! The room was clean, updated amenities, and had a beautiful view. I received clear check-in instructions from the host. The host was also accommodating and helpful. The pool was also a nice addition. Overall, I would definitely stay there again. "
United States
Sonia M.
$256 nightly
The price is $300
Feb 2 - Feb 3
Total with taxes and fees
Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

Charming Studio Apartment with Cold AC in fabulous Makaha

Charming Studio Apartment with Cold AC in fabulous Makaha
Waianae
9.8 out of 10, Exceptional, (16 reviews)
"Perfect hideaway from the city and tourist atmosphere. Friendly and quiet with amenities "
United States
Jennifer W.
$348 nightly
The price is $407
Feb 19 - Feb 20
Total with taxes and fees
Charming Studio Apartment with Cold AC in fabulous Makaha

Studio Nene - Beaches, King Bed, Mountains

Studio Nene - Beaches, King Bed, Mountains
Waianae
10.0 out of 10, Exceptional, (1 review)
"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.
$420 nightly
The price is $491
Feb 7 - Feb 8
Total with taxes and fees
Studio Nene - Beaches, King Bed, Mountains

SERENDIPITY ON THE MOANA - Legal & Oceanfront - Great for Work & Play!

SERENDIPITY ON THE MOANA - Legal & Oceanfront - Great for Work & Play!
Waianae
9.8 out of 10, Exceptional, (157 reviews)
"Beautiful condo!"
United States
Carol W.
$469 nightly
The price is $550
Feb 26 - Feb 27
Total with taxes and fees
SERENDIPITY ON THE MOANA - Legal & Oceanfront - Great for Work & Play!

Studio- Ocean View Hideaway

Studio- Ocean View Hideaway
Waianae
10.0 out of 10, Exceptional, (1 review)
"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.
$455 nightly
The price is $532
Feb 5 - Feb 6
Total with taxes and fees
Studio- Ocean View Hideaway

★Oahu Perfect Vacation • Million Dollar Views, Pool, Spa, Beach, 4BR Sleeps 14★

★Oahu Perfect Vacation • Million Dollar Views, Pool, Spa, Beach, 4BR Sleeps 14★
Waianae
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful family stay in a perfect location!"
United States
Angela C.
$819 nightly
The price is $958
Feb 16 - Feb 17
Total with taxes and fees
★Oahu Perfect Vacation • Million Dollar Views, Pool, Spa, Beach, 4BR Sleeps 14★

Family Oceanview Oasis, Hot Tub, Sleep 12

Family Oceanview Oasis, Hot Tub, Sleep 12
Waianae
10.0 out of 10, Exceptional, (3 reviews)
"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.
$1,282 nightly
The price is $1,500
Feb 5 - Feb 6
Total with taxes and fees
Family Oceanview Oasis, Hot Tub, Sleep 12

Support LOCAL: NEW! Makaha Valley Home

Support LOCAL: NEW! Makaha Valley Home
Makaha Valley
10.0 out of 10, Exceptional, (3 reviews)
"The property was as advertised. The property manager Joe was very helpful with meeting all of our needs and answered my calls promptly. We stayed here to have a siblings reunion and this perfect home and host helped make it a wonderful memory we'll cherish for a long time!"
United States
DITRC U.
Support LOCAL: NEW! Makaha Valley Home

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym
Waianae
10.0 out of 10, Exceptional, (4 reviews)
"Kerstan is an amazing host who responded to our questions and needs tinely. The unit was very clean, and the backyard is like an oasis for the family and kids to enjoy! We got everything we need here !"
Canada
Joyce P.
$1,280 nightly
The price is $1,494
Feb 16 - Feb 17
Total with taxes and fees
4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

Paradise Ocean Mountain Views-comm. pool,spa&gym. Ping Pong, Air Hockey/foosball

Paradise Ocean Mountain Views-comm. pool,spa&gym. Ping Pong, Air Hockey/foosball
Waianae
9.8 out of 10, Exceptional, (9 reviews)
"Can’t wait to come back!"
United States
Manuel A.
$973 nightly
The price is $1,139
Feb 4 - Feb 5
Total with taxes and fees
Paradise Ocean Mountain Views-comm. pool,spa&gym. Ping Pong, Air Hockey/foosball

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym
Waianae
9.0 out of 10, Wonderful, (4 reviews)
"My grandkids are huge historians. They wanted to come see Pearl Harbor, the aviation and other museums. We had an awesome time."
United States
dorothy b.
$916 nightly
The price is $1,071
Feb 7 - Feb 8
Total with taxes and fees
3 BR, Near Beach, Free Prkng, 1 LVL, Pool/Spa, Gym

3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym

3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym
Waianae
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic property."
United States
Charlotte L.
$1,008 nightly
The price is $1,176
Feb 25 - Feb 26
Total with taxes and fees
3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym

Oahu Family cabin_Oceanview and Beach Fun

Oahu Family cabin_Oceanview and Beach Fun
Waianae
10.0 out of 10, Exceptional, (6 reviews)
"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.
$1,352 nightly
The price is $1,588
Feb 6 - Feb 7
Total with taxes and fees
Oahu Family cabin_Oceanview and Beach Fun

4 beds, Near Beach, Pool, Spa, Gym, Ocean Views

4 beds, Near Beach, Pool, Spa, Gym, Ocean Views
Waianae
10.0 out of 10, Exceptional, (6 reviews)
"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.
$1,069 nightly
The price is $1,249
Feb 4 - Feb 5
Total with taxes and fees
4 beds, Near Beach, Pool, Spa, Gym, Ocean Views

3 Bdrm, Near Beach, Sngl LVL, Pool/Spa, Gym, BBQ

3 Bdrm, Near Beach, Sngl LVL, Pool/Spa, Gym, BBQ
Waianae
10.0 out of 10, Exceptional, (1 review)
$1,187 nightly
The price is $1,389
Feb 12 - Feb 13
Total with taxes and fees
3 Bdrm, Near Beach, Sngl LVL, Pool/Spa, Gym, BBQ

Kalo Homes - Makaha Mountain Hideaway

Kalo Homes - Makaha Mountain Hideaway
Waianae
10.0 out of 10, Exceptional, (1 review)
"Host was very communicative and welcoming. Beautiful scenery and quiet community. Loved our stay "
United States
Amy C.
$1,160 nightly
The price is $1,354
Feb 16 - Feb 17
Total with taxes and fees
Kalo Homes - Makaha Mountain Hideaway

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating property and host"
United States
Mike S.
$1,142 nightly
The price is $1,335
Feb 11 - Feb 12
Total with taxes and fees
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ
Waianae
9.8 out of 10, Exceptional, (8 reviews)
"The home was very comfortable. "
United States
Hank A.
$1,398 nightly
The price is $1,631
Feb 23 - Feb 24
Total with taxes and fees
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

Marriott's Ko Olina Beach CluB (1BR)

Marriott's Ko Olina Beach CluB (1BR)
Ko Olina
10.0 out of 10, Exceptional, (1 review)
"Rooms very clean and comfortable. Kitchen well equipped. Lovely views from terrace. Staff always very courteous and friendly. We had a wonderful vacation! Thank you! Aloha !"
United States
Margarita
$913 nightly
The price is $918
Feb 4 - Feb 5
Total with taxes and fees
Marriott's Ko Olina Beach CluB (1BR)

Marriott's Ko Olina Beach CluB (2BR)

Marriott's Ko Olina Beach CluB (2BR)
Ko Olina
8.8 out of 10, Excellent, (6 reviews)
"Great communication with owner. Nice resort and very spacious. "
United States
Diana V.
$1,239 nightly
The price is $1,246
Feb 3 - Feb 4
Total with taxes and fees
Marriott's Ko Olina Beach CluB (2BR)
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 $300 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.