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

Leeward Coast Vacation Rentals

Dates

November 2026

December 2026

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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

Ko Olina

kathryn

CA $750 total

includes taxes & fees

Nov 27 - Nov 28

2. Aulani, Disney Vacation Club Villas

Ko Olina

David

CA $1,054 total

includes taxes & fees

Nov 8 - Nov 9

A resort with a pool, beach, and palm trees.

3. Ko Olina | Beach & Pool Access | Tropical Resort Stay

Ko Olina

heather

CA $819 total

includes taxes & fees

Dec 1 - Dec 2

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

Waianae

Maricruz J.

CA $404 total

includes taxes & fees

Nov 10 - Nov 11

A high-rise hotel with multiple floors, surrounded by lush greenery and a mountainous backdrop.

5. Elite Condo with Spectacular VIEWS ❤️

Waianae

Rose

CA $394 total

includes taxes & fees

Nov 8 - Nov 9

6. Charming Studio Apartment with Cold AC in fabulous Makaha

Waianae

Hope & Furman D.

CA $438 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a front yard, a garage, and a mountain backdrop.

7. Studio Nene - Beaches, King Bed, Mountains

Waianae

Blaine J.

CA $570 total

includes taxes & fees

Nov 22 - Nov 23

A balcony with a view of the ocean, a white sofa, and two chairs.

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

Waianae

Darren

CA $916 total

includes taxes & fees

Nov 29 - Nov 30

A spacious indoor area with high ceilings, large windows, and seating arrangements.

9. Studio- Ocean View Hideaway

Waianae

Naina S.

CA $653 total

includes taxes & fees

Nov 14 - Nov 15

A modern two-story house with a garage, a covered porch, and a well-maintained lawn.

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

Waianae

Angela C.

CA $1,753 total

includes taxes & fees

Nov 14 - Nov 15

A resort with a pool, palm trees, and a view of the ocean at sunset.

11. Marriott's Ko Olina Beach CluB (1BR)

Ko Olina

Robert

CA $1,161 total

includes taxes & fees

Nov 8 - Nov 9

A hotel with a view of the ocean, palm trees, and a beach with umbrellas.

12. Ko Olina | Beach & Pool Access | Tropical Resort Stay

Ko Olina

CA $843 total

includes taxes & fees

Dec 1 - Dec 2

A hot tub with steps leading up to a deck, surrounded by a stone pathway and a covered seating area with string lights.

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

Waianae

Steven M.

CA $1,791 total

includes taxes & fees

Nov 18 - Nov 19

A modern two-story house with a patio, outdoor seating, and a mountain backdrop.

14. Hot Tub|Mountain Views|Beach 5 Min|Free Parking

Waianae

Raina G.

CA $1,740 total

includes taxes & fees

Nov 10 - Nov 11

A patio area with a wooden fence, outdoor seating, and string lights.

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

Waianae

Winston B.

CA $1,931 total

includes taxes & fees

Dec 2 - Dec 3

A patio with outdoor furniture, a grill, and a view of a lush green hillside.

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

Waianae

Chris M.

CA $1,567 total

includes taxes & fees

Nov 11 - Nov 12

A dining area with a table set for two, a large tropical plant, and a view of the ocean through a sliding glass door.

17. Lani Kai Ocean View Villa, Sleeps 8 Pool + Hot Tub. Family-Friendly! Privacy!

Waianae

CA $1,788 total

includes taxes & fees

Nov 14 - Nov 15

A swimming pool with lounge chairs, a poolside area, and a view of a mountain.

18. Affordable Luxury-Tropical Ohana in Million Gated Comm-Pingpong/Foosbal/Rec Area

Waianae

Michelle H.

CA $1,527 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with wooden cabinets, a central island, and a dining area with a round table and chairs.

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

Waianae

Chris W.

CA $1,387 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a large island, pendant lights, and a view of the ocean.

20. Ocean View - Game RM,Free Parking,BBQ,Beach 5 Min

Waianae

Anonymous traveller

CA $1,748 total

includes taxes & fees

Nov 8 - Nov 9

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Find vacation rentals that suit your style

Top Leeward Coast Hotel Reviews

A living room with a sofa, a coffee table, and a view of the ocean through large windows.

Partial Ocean View Condo with King or Queen Bed and Parking

Waikiki

10/10 Excellent

Anonymous traveller

A poolside area with a fire feature, lounge chairs, and a view of a hotel building.

Hyatt House at Ho'opili

Ewa Beach

10/10 Excellent

Brian

A resort with a swimming pool, beach view, palm trees, and lounge chairs.

The Kahala Hotel & Resort

Kahala

10/10 Excellent

The staff are the friendliest and most helpful I have ever experienced in a lifetime of travels. The resort was very clean and well kept. The location is convenient for reaching most of the island to sight see, shop, and go to venues for events. It is true the west side resorts would probably get a little more sun, but you can only be out in the sun so much, and those ones (Ko Olina) are quite remote from the other things I mentioned. The beach is safe and fairly private. The water is well...

Mark

A modern apartment with a kitchen, dining area, and a balcony with a view of the ocean.

Midway at the Waikiki Banyan

Waikiki

10/10 Excellent

Tanya

A poolside area with lounge chairs and umbrellas, overlooking the ocean at sunset.

Halepuna Waikiki by Halekulani

Waikiki

10/10 Excellent

Just the best place. The staff goes above and beyond, and everything is beautifully appointed. Yoga in the garden was lovely, the Toto toilets are a great touch, the rooms are stunning and we can’t wait to come back. What a pleasure. Shout outs to Yuki and Jerome at the pool work who hustle hard to keep everyone comfortable, and the team at the valet desk are charming and helpful - thank you everyone! My only downside was that the pool closes at sunset, we love a night swim - but we...

Chelsea

A hotel with outdoor seating, a pool, and a prominent building with a triangular roof structure.

OUTRIGGER Reef Waikiki Beach Resort

Waikiki

10/10 Excellent

This was our first time in Hawaii and we originally wanted to book the Hilton hawaiian village, but there was a strike at the time and decided to change our plans. This hotel in the perfect location. A ton of shopping and food options surrounding the hotel. 2 restaurants and an ABC store on grounds. The pool was a bit small but great for kids. Our room was immaculate and had a beautiful 2 queen bed room with 2 walls of floor to ceiling windows with 2 balconies. I would recommend it to anyone.

Tanya

A modern living room with a large window, a sofa, a dining table with a fruit bowl and glasses, and a kitchen area with a TV.

High Floor Mountain View with King or Queen Bed and Parking

Waikiki

10/10 Excellent

Asif

A modern living room with a large sectional sofa, a dining table, and a view of the cityscape through large windows.

Premium Remodeled Condo in Waikiki with 2 Beds and Parking

Waikiki

10/10 Excellent

JACK

A pool area with a waterfall, lounge chairs, and tropical plants.

Embassy Suites By Hilton Oahu Kapolei

City Center

10/10 Excellent

Devinder Singh

A modern outdoor lounge area with a staircase, seating, and a variety of plants.

AC Hotel by Marriott Honolulu

Downtown Honolulu

10/10 Excellent

Bernadette

A balcony with wicker chairs, a clock, and a view of the ocean and hotel buildings.

Embassy Suites by Hilton Waikiki Beach Walk

Waikiki

10/10 Excellent

Adam Larry

A view of a beach with a sailboat, palm trees, and a building with balconies.

Vive Hotel Waikiki

Waikiki

10/10 Excellent

Angelina

A Tropics restaurant with a stone facade, outdoor seating, and a view of the ocean.

Hilton Grand Vac Club The Grand Islander Waikiki Honolulu

Waikiki

10/10 Excellent

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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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leeward Coast vacation rentals we have selected for you start as low as CA $102 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 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.

Leeward Coast Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Leeward Coast vacation rentals

1. Marriott's Ko'Olina Beach Club

2. Aulani, Disney Vacation Club Villas

3. Ko Olina | Beach & Pool Access | Tropical Resort Stay

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

5. Elite Condo with Spectacular VIEWS ❤️

6. Charming Studio Apartment with Cold AC in fabulous Makaha

7. Studio Nene - Beaches, King Bed, Mountains

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

9. Studio- Ocean View Hideaway

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

11. Marriott's Ko Olina Beach CluB (1BR)

12. Ko Olina | Beach & Pool Access | Tropical Resort Stay

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

14. Hot Tub|Mountain Views|Beach 5 Min|Free Parking

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

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

17. Lani Kai Ocean View Villa, Sleeps 8 Pool + Hot Tub. Family-Friendly! Privacy!

18. Affordable Luxury-Tropical Ohana in Million Gated Comm-Pingpong/Foosbal/Rec Area

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

20. Ocean View - Game RM,Free Parking,BBQ,Beach 5 Min

Find vacation rentals that suit your style

Top Leeward Coast Hotel Reviews

Partial Ocean View Condo with King or Queen Bed and Parking

10/10 Excellent

Find out more about Leeward Coast

Leeward Coast vacation rentals: An excellent choice for every season

How to find incredible deals on Leeward Coast rentals

Explore a world of travel with Expedia