A beach with rocks, ocean waves, and palm trees under a colorful sunset sky.

Leeward Coast Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Leeward Coast vacation rentals

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

Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!
Waianae
8.0 out of 10, Very Good, (164 reviews)
"Perfect place for 2 college students on a budget! Incredible views of both the mountains and ocean!"
United States
hannah c.
$257 nightly
The price is $301
Aug 18 - Aug 19
Total with taxes and fees
Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

2. Elite Condo with Spectacular VIEWS ❤️

Elite Condo with Spectacular VIEWS ❤️
Waianae
7.6 out of 10, Good, (118 reviews)
"I love staying here, it’s very relaxing and the views from up here is beautiful "
United States
Kealoha G.
$252 nightly
The price is $295
Aug 17 - Aug 18
Total with taxes and fees
Elite Condo with Spectacular VIEWS ❤️

3. Charming Studio Apartment with Cold AC in fabulous Makaha

Charming Studio Apartment with Cold AC in fabulous Makaha
Waianae
8.8 out of 10, Excellent, (32 reviews)
"Clean and nice place to stay. It met our needs while we were there."
United States
bryon S.
$314 nightly
The price is $367
Aug 21 - Aug 22
Total with taxes and fees
Charming Studio Apartment with Cold AC in fabulous Makaha

4. Studio Nene - Beaches, King Bed, Mountains

Studio Nene - Beaches, King Bed, Mountains
Waianae
10.0 out of 10, Exceptional, (4 reviews)
"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.
$357 nightly
The price is $418
Aug 15 - Aug 16
Total with taxes and fees
Studio Nene - Beaches, King Bed, Mountains

5. Studio- Ocean View Hideaway

Studio- Ocean View Hideaway
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely loved the place! Would definitely come back- the hosts outdid themselves. Everything was accounted for that we could possibly need! Can’t wait to come back. "
United States
Naina S.
$428 nightly
The price is $501
Aug 18 - Aug 19
Total with taxes and fees
Studio- Ocean View Hideaway

6. Sleep 12, Hot Tub, Beach 5 min, Oahu West Side

Sleep 12, Hot Tub, Beach 5 min, Oahu West Side
Waianae
10.0 out of 10, Exceptional, (4 reviews)
"We had an awesome stay, the rooms were really spacious and super clean. The interior is calm and welcoming, everything was at its proper place and well furnished. Our 16 month old had a time of her life running around bare foot in the large house! The host (emma) is very kind, super responsive, and flexible. I wish we had stayed longer. "
United States
Rajarshi
$1,223 nightly
The price is $1,431
Aug 20 - Aug 21
Total with taxes and fees
Sleep 12, Hot Tub, Beach 5 min, Oahu West Side

7. 🏄‍♀️ Villa Aloha · 4 Bedrooms, Pool, spa, Sleeps 12 Oahu Top New Home 🏝️

🏄‍♀️ Villa Aloha · 4 Bedrooms, Pool, spa, Sleeps 12 Oahu Top New Home 🏝️
Waianae
10.0 out of 10, Exceptional, (1 review)
"We had an amazing time! There were 5 adults and 5 kids and we still felt like we had plenty of room. The arcade games and the garage space were perfect for our teens. Our host was very communicative and everything was laid out very nicely for us. We would 100% recommend staying here!"
United States
Mandi B.
$897 nightly
The price is $1,050
Sep 9 - Sep 10
Total with taxes and fees
🏄‍♀️ Villa Aloha · 4 Bedrooms, Pool, spa, Sleeps 12 Oahu Top New Home 🏝️

8. 4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng
Waianae
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful views, great host, away from the hustle and bustle of mega hotels. "
United States
Winston B.
$1,061 nightly
The price is $1,243
Aug 18 - Aug 19
Total with taxes and fees
4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

9. 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.
$1,141 nightly
The price is $1,334
Sep 8 - Sep 9
Total with taxes and fees
4 beds, Near Beach, Pool, Spa, Gym, Ocean Views

10. 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, (8 reviews)
"The home is beautiful and well-stocked. The view from the backyard is breathtaking, and at sunset it's unreal. The amenities on-site gym/pool were close and easy to use. Definitely will book again. "
United States
wess m.
$1,233 nightly
The price is $1,441
Sep 8 - Sep 9
Total with taxes and fees
4 BDRM, Near beach, Ocean Views, HotTub, Pool, Gym

11. Mystic Mermaid Island Retreat! Entire Home

Mystic Mermaid Island Retreat! Entire Home
Waianae
10.0 out of 10, Exceptional, (3 reviews)
"Everything about this house was perfect. Location, view, cleanliness, amenities. We would definitely stay again…this might be our new favorite side of the island."
United States
Rachael F.
$998 nightly
The price is $1,170
Sep 1 - Sep 2
Total with taxes and fees
Mystic Mermaid Island Retreat! Entire Home

12. 4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym

4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Had a wonderful stay here with family. Location had very beautiful views of the Ocean and Mountains. "
United States
Anonymous traveler
$1,165 nightly
The price is $1,360
Aug 17 - Aug 18
Total with taxes and fees
4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym

13. 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, (8 reviews)
"Perfect visit. What an awesome space. "
United States
Chris W.
$916 nightly
The price is $1,071
Aug 31 - Sep 1
Total with taxes and fees
3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym

14. 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, (9 reviews)
"We really enjoyed our stay at this property. The house was extremely clean and the kitchen was well stocked. The backyard is beautifully landscaped with plenty of seating as well as a hot tub. We really appreciated the beach towels, coolers, boards, etc. Having those things available made our time at the beach that much more enjoyable. Kerstan is an excellent host who communicated with us throughout our stay. I highly recommend this property. "
United States
Kathryn P.
$1,139 nightly
The price is $1,336
Aug 15 - Aug 16
Total with taxes and fees
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

15. 4 Bdrm, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

4 Bdrm, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng
Makaha Valley
10.0 out of 10, Exceptional, (1 review)
"Beautiful home with a beautiful view. Our family of eight stayed comfortably in the home, we all had plenty of space."
United States
Jessica E.
$1,188 nightly
The price is $1,387
Sep 2 - Sep 3
Total with taxes and fees
4 Bdrm, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

16. Kalo Collective ~ Mauka to Makai

Kalo Collective ~ Mauka to Makai
Waianae
10.0 out of 10, Exceptional, (6 reviews)
"The host was very attentive and was in constant touch with me on how our stay was and if we needed anything. The house was beautiful and was perfect for our trip. The house was in a gated community so we felt safe and was away from all the hustle and bustle. If we ever do get to come back, I would definitely stay here again!! "
United States
Raina G.
$1,112 nightly
The price is $1,299
Aug 16 - Aug 17
Total with taxes and fees
Kalo Collective ~ Mauka to Makai

17. 3BR, Near Beach, Game RM, Private Spa, Pool, Gym

3BR, Near Beach, Game RM, Private Spa, Pool, Gym
Waianae
10.0 out of 10, Exceptional, (24 reviews)
"This property is immaculate and we had a wonderful stay! "
United States
Sarah P.
$1,215 nightly
The price is $1,419
Sep 9 - Sep 10
Total with taxes and fees
3BR, Near Beach, Game RM, Private Spa, Pool, Gym

18. 4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym

4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Host was very communicative and welcoming. Beautiful scenery and quiet community. Loved our stay "
United States
Amy C.
4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym

19. 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.
$1,163 nightly
The price is $1,359
Sep 10 - Sep 11
Total with taxes and fees
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

20. Single-Level Family Home | Hot Tub, Pool, Gym, Gated Community

Single-Level Family Home | Hot Tub, Pool, Gym, Gated Community
Waianae
10.0 out of 10, Exceptional, (1 review)
$1,250 nightly
The price is $1,462
Sep 9 - Sep 10
Total with taxes and fees
Single-Level Family Home | Hot Tub, Pool, Gym, Gated Community
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

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 $607 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.

Explore a world of travel with Expedia