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Leeward Coast Holiday Rentals

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Our top choices for Leeward Coast holiday rentals

1. 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.
The price is NZ$487
includes taxes & fees
28 Aug - 29 Aug
Elite Condo with Spectacular VIEWS ❤️

2. 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.
The price is NZ$428
includes taxes & fees
6 Sept - 7 Sept
Enjoy Breathtaking Views of the Ocean and Gorgeous Mountains!!! Newly Renovated!

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, (33 reviews)
"Clean and nice place to stay. It met our needs while we were there."
United States
bryon S.
The price is NZ$617
includes taxes & fees
9 Sept - 10 Sept
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.
The price is NZ$702
includes taxes & fees
24 Aug - 25 Aug
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.
The price is NZ$841
includes taxes & fees
19 Aug - 20 Aug
Studio- Ocean View Hideaway

6. 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.
The price is NZ$2,043
includes taxes & fees
19 Aug - 20 Aug
4 BR, Near Beach, Pool/Spa, Gym, BBQ, Free Prkng

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.
The price is NZ$1,740
includes taxes & fees
9 Sept - 10 Sept
🏄‍♀️ Villa Aloha · 4 Bedrooms, Pool, spa, Sleeps 12 Oahu Top New Home 🏝️

8. 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
The price is NZ$2,296
includes taxes & fees
19 Aug - 20 Aug
Sleep 12, Hot Tub, Beach 5 min, Oahu West Side

9. 🌺Oahu Million Dollar Ocean View • Sleeps 14, Pool, Spa, Near Beach, w/AC, BBQ🌺

🌺Oahu Million Dollar Ocean View • Sleeps 14, Pool, Spa, Near Beach, w/AC, BBQ🌺
Waianae
9.8 out of 10, Exceptional, (22 reviews)
"Beautiful location with mountain and ocean views right next to the pool. Your home was spacious enough for myself and my family. We loved the personal welcome with my name when we came through the door. The full kitchen and grill we used alot enjoying eachothers company at the 8 top kitchen table. Definitely would recommend this house to family and friends and will definitely return and rent again"
United States
Kehaulani O.
The price is NZ$1,886
includes taxes & fees
15 Sept - 16 Sept
🌺Oahu Million Dollar Ocean View • Sleeps 14, Pool, Spa, Near Beach, w/AC, BBQ🌺

10. 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
The price is NZ$1,884
includes taxes & fees
27 Aug - 28 Aug
Lani Kai Ocean View Villa, Sleeps 12 Pool + Hot Tub. Family-Friendly! Privacy!

11. 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.
The price is NZ$1,812
includes taxes & fees
31 Aug - 1 Sept
3 Bdrm, Sngl Lvl, Near Beach, BBQ, Pool/Spa, Gym

12. 🤙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, (10 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.
The price is NZ$2,085
includes taxes & fees
28 Aug - 29 Aug
🤙The Makaha Shaka! 🤙3BR Villa Oahu 5 Min to Beach, Ocean View, Pool, Hot Tub

13. 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.
The price is NZ$2,234
includes taxes & fees
8 Sept - 9 Sept
4 beds, Near Beach, Pool, Spa, Gym, Ocean Views

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

Ko Olina | Beach & Pool Access | Tropical Resort Stay
Ko Olina
9.6 out of 10, Exceptional, (130 reviews)
"Great stay. Host was very responsive and helpful. Great value with resort pool and easy access to the lagoons. Hope to come again soon."
United States
Kyle M.
The price is NZ$819
includes taxes & fees
1 Sept - 2 Sept
Ko Olina | Beach & Pool Access | Tropical Resort Stay

15. Aulani, Disney Vacation Club Villas

Aulani, Disney Vacation Club Villas
5.0 star property
Ko Olina
8.8 out of 10, Excellent, (1,013 reviews)
"This is an amazing property that is very clean and family friendly!!"
United States
Brian
The price is NZ$1,317
includes taxes & fees
31 Aug - 1 Sept
Aulani, Disney Vacation Club Villas

16. 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 traveller
The price is NZ$2,199
includes taxes & fees
31 Aug - 1 Sept
4 BDRM, Near beach, Free Prking, HotTub, Pool, Gym

17. Marriott's Ko'Olina Beach Club

Marriott's Ko'Olina Beach Club
4.0 star property
Ko Olina
8.8 out of 10, Excellent, (1,018 reviews)
"Room was very clean and the food was excellent. Staff was extremely friendly and helpful"
United States
Carole
The price is NZ$1,028
includes taxes & fees
31 Aug - 1 Sept
Marriott's Ko'Olina Beach Club

18. 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.
The price is NZ$2,273
includes taxes & fees
10 Sept - 11 Sept
Kalo Collective ~ Mauka to Makai

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.
The price is NZ$2,215
includes taxes & fees
16 Sept - 17 Sept
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ

20. 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, (10 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.
The price is NZ$2,355
includes taxes & fees
8 Sept - 9 Sept
4BR, Near Beach, Pool/Spa, Gym, Free Parking, BBQ
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leeward Coast holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leeward Coast. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Leeward Coast. Seeing all the best attractions is bound to make you fall in love with Leeward Coast. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Leeward Coast short-term rentals, that won’t be hard to do.

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