Find monthly stays across Windward’s neighborhoods.
Where to stay in Windward
Design-led rooms, walkable streets, and neighborhoods worth staying in rather than passing through.
Monthly Stays preferred by Windward travelers
A curated selection of Windward monthly stays chosen for their location, design, and overall stay experience across the city.
9.5
Private Beach
Oceanfront
Breakfast
EV Charge Station
Parking
Balcony/Terrace
View
Air Conditioner
9.7- Private Beach
- Oceanfront
- Breakfast
- EV Charge Station
9.6
Hot Tub- Parking
Pool- Balcony/Terrace
Places made for checking in and heading out.
Each part of Windward offers its own way to spend the stay, from the streets you walk in the morning to the tables you end up at after dark.
More places that leave room for discovery.
From quick city breaks to longer stays, explore more Windward monthly stays chosen for design, comfort, and easy access to the neighborhoods you came to see.
9.0- Oceanfront
- Parking
Ocean View- Balcony/Terrace
How stays in Windward are booked.
Discover a stay
Browse a curated selection of Windward hotels, shaped by location, design, and experience.
Review the details
Explore layout, amenities, and the neighborhood to see how each stay fits your trip.
Reserve through a partner
Complete your booking securely through a trusted partner, with confirmation handled there.
Pick the kind of stay that fits your trip.
Every trip to Windward is different. These feeds sort Windward monthly stays by what matters most to the way you want to travel.
Business Hotels & Aparthotels in Windward
Work-Friendly Stays for Business Trips in Windward
10.0- Air Conditioner
Internet
Pet Friendly
Child Friendly
9.0- Parking
- Pool
- Balcony/Terrace
- View
- Parking
- Pool
- View
- Air Conditioner
- Parking
- Pool
Kitchen- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Internet
9.8- Parking
- Balcony/Terrace
- View
- Air Conditioner
9.3- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Parking
- Pool
- View
- Air Conditioner
Long-Stay Hotels & Apartments in Windward
Comfortable Extended Stays with Space to Settle In
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
9.8- Parking
- Pool
- Balcony/Terrace
- View
7.9- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Internet
7.9- EV Charge Station
- Parking
- Balcony/Terrace
- View
9.3- Parking
- Pool
- Balcony/Terrace
- View
9.6- Parking
- Pool
- Balcony/Terrace
- View
Wellness Hotels & Stays in Windward
Relaxing Stays Designed to Help You Rest, Recharge, and Reset
Everything to know before you check in to
Windward.
There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in Windward:
There are 64 monthly stays available for rent in Windward.
There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in Windward:
There are 64 monthly stays available for rent in Windward.
