Search Windward Coast Cottage Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul
In one month
1 Aug - 3 Aug
In two months
29 Aug - 31 Aug

Featured Cottages in Windward Coast

Mauna View by Avantstay 10min to Beach, Backyard
Front of property

Mauna View by Avantstay 10min to Beach, Backyard

3.0 star property
8.0 out of 10, Very good, (2)
"We had a wonderful stay. Property was as pictured. The biggest challenges we found is that the area you need to drive through to get to the property is very run down. The property is about a 30 min drive from any safe amenity such as a grocery, gas station etc. If you want to just stay in one place your whole trip this is the place. But if you want to explore around it is not. I would have liked the property to have also listed that there were things like - washer and dryer, hair dryer, general...
Mauna View by Avantstay 10min to Beach, Backyard
Cottage Nene by Avantstay Mountain View + Garden
Interior

Cottage Nene by Avantstay Mountain View + Garden

3.0 star property
Cottage Nene by Avantstay Mountain View + Garden
Alaula by Avantstay Gated Security Home w Valley, Ocean Views!
Front of property

Alaula by Avantstay Gated Security Home w Valley, Ocean Views!

3.0 star property
Alaula by Avantstay Gated Security Home w Valley, Ocean Views!
'olu'olu by Avantstay Single-story Home by Ocean
Front of property

'olu'olu by Avantstay Single-story Home by Ocean

3.0 star property
'olu'olu by Avantstay Single-story Home by Ocean
@ Marbella Lane - Stylish House + Impressive Views
4 bedrooms, desk, laptop workspace, iron/ironing board

@ Marbella Lane - Stylish House + Impressive Views

3.0 star property
@ Marbella Lane - Stylish House + Impressive Views
Marbella Lane Nohea Stylish Home Makaha
Private kitchen

Marbella Lane Nohea Stylish Home Makaha

4.0 star property
Marbella Lane Nohea Stylish Home Makaha
Aloha Breeze by Avantstay Ocean View, Near Beach
Front of property

Aloha Breeze by Avantstay Ocean View, Near Beach

3.0 star property
Aloha Breeze by Avantstay Ocean View, Near Beach
@ Marbella Lane - Serene & Lovely MT + Ocean Views
3 bedrooms, travel cot, bed sheets

@ Marbella Lane - Serene & Lovely MT + Ocean Views

3.0 star property
@ Marbella Lane - Serene & Lovely MT + Ocean Views
Modern Waianae Home w/ Mountain & Valley View
Living area

Modern Waianae Home w/ Mountain & Valley View

3.0 star property
Modern Waianae Home w/ Mountain & Valley View
@ Marbella Lane - Pōmaika'i Ocean Love Paradise
Private kitchen

@ Marbella Lane - Pōmaika'i Ocean Love Paradise

3.0 star property
@ Marbella Lane - Pōmaika'i Ocean Love Paradise
@ Marbella Lane - Paradise Point Close to Beaches
4 bedrooms, desk, laptop workspace, iron/ironing board

@ Marbella Lane - Paradise Point Close to Beaches

3.0 star property
@ Marbella Lane - Paradise Point Close to Beaches
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
Sign in
Sign up, it's free

Frequently asked questions

Are there any family-friendly cottages in Windward Coast?
If you want to be close to nature in Windward Coast, we recommend Newly Renovated Lanikai, Steps To Ocean A. With a 3-star rating and amenities like an oven and a king-sized bed, you'll find it easy to get comfortable at this family-friendly cottage. Windward Coast has no shortage of family-friendly attractions to explore that'll keep the kids entertained. Lanikai Beach and Kailua Beach deliver fun for visitors of all ages.
Why book your cottage in Windward Coast with Expedia?
Expedia has some terrific cottages in Windward Coast, so get set for an unforgettable stay on nature's doorstep. If you have a certain budget, choose how much you'd like to spend and the star rating of your property. Or, make use of our filters to search for cottages with a pool or free WiFi. We'll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Windward Coast?
With Expedia's convenient filter tool, booking cheap cottages in Windward Coast couldn't be easier. To discover accommodation that are friendly on the wallet, refine your search by star rating, amenities and budget.