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

Leeward Coast Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Leeward Coast vacation rentals

A resort with multiple swimming pools, palm trees, and a beach.

1. Marriott's Ko'Olina Beach Club

Marriott's Ko'Olina Beach Club
4.0 star property
Ko Olina
8.8 out of 10, Excellent, (1,028 reviews)
"we enjoyed our stay. The staff was friendly and helpful."
United States
kathryn
$511 nightly
The price is $607
Oct 12 - Oct 13
Total with taxes and fees
Marriott's Ko'Olina Beach Club
A beach with clear turquoise water, a sandy shore, and a rocky outcrop.

2. Elite Condo with Spectacular VIEWS ❤️

Elite Condo with Spectacular VIEWS ❤️
Waianae
7.8 out of 10, Good, (123 reviews)
"Room was very nice . The vie w was awesome. Nice quite no one bothered you. Security was very nice to see there. There is a bus stop there if you don’t have a car. It’s peaceful and beautiful."
United States
Rose
$270 nightly
The price is $318
Oct 5 - Oct 6
Total with taxes and fees
Elite Condo with Spectacular VIEWS ❤️
A coastal town with clear turquoise waters, a sandy beach, and a rocky breakwater.

3. 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.
$346 nightly
The price is $407
Oct 4 - Oct 5
Total with taxes and fees
Studio Nene - Beaches, King Bed, Mountains

4. 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, (168 reviews)
"Perfect place for 2 college students on a budget! Incredible views of both the mountains and ocean!"
United States
hannah c.
$245 nightly
The price is $288
Oct 1 - Oct 2
Total with taxes and fees
Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

5. Aulani, Disney Vacation Club Villas

Aulani, Disney Vacation Club Villas
5.0 star property
Ko Olina
9.0 out of 10, Wonderful, (1,026 reviews)
"Beautiful Resort"
United States
Karla
$634 nightly
The price is $752
Oct 16 - Oct 17
Total with taxes and fees
Aulani, Disney Vacation Club Villas
A beach with clear turquoise water, a sandy shore, and a rocky outcrop.

6. Charming Studio Apartment with Cold AC in fabulous Makaha

Charming Studio Apartment with Cold AC in fabulous Makaha
Waianae
9.0 out of 10, Wonderful, (34 reviews)
"Clean and nice place to stay. It met our needs while we were there."
United States
bryon S.
$265 nightly
The price is $312
Sep 30 - Oct 1
Total with taxes and fees
Charming Studio Apartment with Cold AC in fabulous Makaha
A patio with outdoor furniture, a grill, and a view of a lush green hillside.

7. 🤙The Makaha Shaka! 🤙3BR Villa Oahu 5 Min to Beach, Ocean View, Pool, Hot Tub

🤙The Makaha Shaka! 🤙3BR Villa Oahu 5 Min to Beach, Ocean View, Pool, Hot Tub
Waianae
10.0 out of 10, Exceptional, (11 reviews)
"Great communication with Emma. The house is lovely and the living space was especially great for a women’s group trip. We would stay here again!"
United States
Christina P.
$873 nightly
The price is $1,030
Oct 10 - Oct 11
Total with taxes and fees
🤙The Makaha Shaka! 🤙3BR Villa Oahu 5 Min to Beach, Ocean View, Pool, Hot Tub
A modern two-story house with a garage, a covered porch, and a well-maintained lawn.

8. 🌺 Oahu Ocean & Mountain Views • Sleeps 14 • Pool, Spa, Near Beach, AC & BBQ 🌺

🌺 Oahu Ocean & Mountain Views • Sleeps 14 • Pool, Spa, Near Beach, AC & BBQ 🌺
Waianae
9.8 out of 10, Exceptional, (23 reviews)
"Wonderful family stay in a perfect location!"
United States
Angela C.
$852 nightly
The price is $1,004
Oct 2 - Oct 3
Total with taxes and fees
🌺 Oahu Ocean & Mountain Views • Sleeps 14 • Pool, Spa, Near Beach, AC & BBQ 🌺
A spacious indoor area with high ceilings, large windows, and seating arrangements.

9. 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.
$401 nightly
The price is $472
Oct 11 - Oct 12
Total with taxes and fees
Studio- Ocean View Hideaway
A residential area with a house featuring a large deck and outdoor furniture, surrounded by a white fence, with a mountainous backdrop.

10. 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
10.0 out of 10, Exceptional, (16 reviews)
"What a wonderful stay! House was wonderful, host was incredible. Would recommend to anyone looking for a great stay. "
United States
Michelle H.
$920 nightly
The price is $1,084
Sep 29 - Sep 30
Total with taxes and fees
Paradise Ocean Mountain Views-comm. pool,spa&gym. Ping Pong, Air Hockey/foosball
An outdoor dining area with a view of a mountainous landscape, a white fence, and a house with a balcony.

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

Sleep 12, Hot Tub, Beach 5 min, Oahu West Side
Waianae
9.4 out of 10, Exceptional, (6 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
$1,109 nightly
The price is $1,306
Oct 5 - Oct 6
Total with taxes and fees
Sleep 12, Hot Tub, Beach 5 min, Oahu West Side
A beach with surfers, clear blue water, and a mountain in the background.

12. Ocean+Mountain View|Free Parking|BBQ|Beach 5 Min

Ocean+Mountain View|Free Parking|BBQ|Beach 5 Min
Waianae
10.0 out of 10, Exceptional, (3 reviews)
"Everything was wonderful and our host was most accommodating and easy to work with."
United States
Wendi H.
$1,011 nightly
The price is $1,189
Oct 2 - Oct 3
Total with taxes and fees
Ocean+Mountain View|Free Parking|BBQ|Beach 5 Min
A beach with clear blue waters, a sandy shore, and palm trees.

13. Beach 5 Min|Community Pool+Gym|Free Parking

Beach 5 Min|Community Pool+Gym|Free Parking
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.
$1,019 nightly
The price is $1,200
Oct 14 - Oct 15
Total with taxes and fees
Beach 5 Min|Community Pool+Gym|Free Parking
A residential area with houses, a well-maintained lawn, and outdoor seating areas.

14. 🏄‍♀️ 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
9.4 out of 10, Exceptional, (3 reviews)
"We absolutely loved our stay here! From the moment we arrived, everything felt comfortable, clean, and welcoming. The property was beautiful, very well-maintained, and the view was honestly one of our favorite parts of the stay. Waking up and enjoying that scenery made our Hawaii vacation even more special. Everything was just perfect for us, and we had such a relaxing and enjoyable experience. We were very happy with our stay and would definitely come back again the next time we’re in Hawaii....
United States
Dhu
$838 nightly
The price is $988
Sep 30 - Oct 1
Total with taxes and fees
🏄‍♀️ Villa Aloha · 4 Bedrooms, Pool, spa, Sleeps 12 Oahu Top New Home 🏝️
An outdoor patio with a table and seating, overlooking a lush green landscape and mountains.

15. 2 King Beds|Beach 5 Min|BBQ|Free Parking

2 King Beds|Beach 5 Min|BBQ|Free Parking
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.
$939 nightly
The price is $1,104
Oct 1 - Oct 2
Total with taxes and fees
2 King Beds|Beach 5 Min|BBQ|Free Parking
A beach with surfers, clear blue water, and a mountain in the background.

16. Single Level Home|Community Pool+Gym|Beach 5 Min

Single Level Home|Community Pool+Gym|Beach 5 Min
Waianae
10.0 out of 10, Exceptional, (8 reviews)
"Perfect visit. What an awesome space. "
United States
Chris W.
$871 nightly
The price is $1,025
Oct 12 - Oct 13
Total with taxes and fees
Single Level Home|Community Pool+Gym|Beach 5 Min
A covered outdoor seating area with a fire pit, surrounded by lush greenery and a view of the ocean and mountains.

17. Ocean Views|Beach 5 Min|Free Parking|Hot Tub

Ocean Views|Beach 5 Min|Free Parking|Hot Tub
Waianae
10.0 out of 10, Exceptional, (8 reviews)
"Great place clean and quiet. Beautiful yard for children"
United States
Eric L.
$1,139 nightly
The price is $1,340
Oct 14 - Oct 15
Total with taxes and fees
Ocean Views|Beach 5 Min|Free Parking|Hot Tub
A hot tub with steps leading up to a deck, surrounded by a stone pathway and a covered seating area with string lights.

18. Single LVL Home|Beach 5 Min|Fire Pit|Free Parking

Single LVL Home|Beach 5 Min|Fire Pit|Free Parking
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Everything made it a great stay. Great communication from the host. Place was very clean and well maintained. Plenty of supplies."
United States
Steven M.
$1,039 nightly
The price is $1,222
Oct 7 - Oct 8
Total with taxes and fees
Single LVL Home|Beach 5 Min|Fire Pit|Free Parking
A dining area with a table set for two, a large tropical plant, and a view of the ocean through a sliding glass door.

19. Lani Kai Ocean View Villa, Sleeps 12 Pool + Hot Tub. Family-Friendly! Privacy!

Lani Kai Ocean View Villa, Sleeps 12 Pool + Hot Tub. Family-Friendly! Privacy!
Waianae
$879 nightly
The price is $1,036
Oct 11 - Oct 12
Total with taxes and fees
Lani Kai Ocean View Villa, Sleeps 12 Pool + Hot Tub. Family-Friendly! Privacy!
A two-story house with a stone pathway leading to a patio area, a barbecue grill, and a small garden.

20. Beach 5 Min|BBQ|Community Pool+Gym|Free Parking

Beach 5 Min|BBQ|Community Pool+Gym|Free Parking
Waianae
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating property and host"
United States
Mike S.
$1,069 nightly
The price is $1,257
Oct 7 - Oct 8
Total with taxes and fees
Beach 5 Min|BBQ|Community Pool+Gym|Free 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.
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Top Leeward Coast Hotel Reviews

Hawaiian Princess at Makaha Beach

Hawaiian Princess at Makaha Beach

10/10 Excellent
"Great secluded beach front stay! I was able to get up early and start snorkeling without the hassle of having to drive somewhere. Please plan to help keep the area clean and if you go snorkeling please help clean up the debris in the water. The only down side is if you want to travel to other parts of the island it will take you longer. Overall it was a great stay! I will be staying here again!"
Joseph 3-night trip
Posted 6 hours ago
Hawaiian Princess at Makaha Beach

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 $579 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.

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