HouseStay has supported families seeking flexible, temporary housing solutions. For job relocations, snowbirds, and military reassignments, Winter Garden has been a reliable destination for those needing a comfortable place to land.
In recent months, we’ve listed 16 fully furnished rentals, including 16 apartments. These properties were equipped with amenities like No Smoking Allowed, Full Kitchen, and Family Friendly—perfect for creating a space that truly felt like home. Many rentals also included convenient utilities such as Trash Pick Up, WiFi, and Cable TV.
The average monthly rent for a 1 bedroom / 1 bath Apartment in Winter Garden has hovered around $4,234 but have ranged between $2,578 and $7,695, giving future renters a helpful benchmark as they plan ahead. If you like Winter Garden, consider checking out nearby properties in Clermont, Orlando, Four Corners, Reunion, and Kissimmee, where similar family friendly monthly housing options may be available. Our listings are always being updated, so be sure to check back soon for new opportunities in Winter Garden!
HouseStay has offered a wide selection of Winter Garden, FL properties that met the evolving needs of digital nomads, remote workers, consultants, and other location-flexible professionals. These past rentals were in popular Winter Garden neighborhoods, and included 16 apartments.
Each property was thoughtfully equipped with amenities that support a productive remote lifestyle—like No Smoking Allowed, Full Kitchen, and Family Friendly—creating an environment that balances work and relaxation. Utilities such as Trash Pick Up, WiFi, and Cable TV were commonly included to make extended stays seamless and stress-free.
The average availability of 16 fully furnished properties in the past reflects Winter Garden’s popularity among traveling professionals seeking temporary housing. Rental pricing for a 1 bedroom / 1 bath Apartment has averaged around $4,234 per month, with prices ranging from $2,578 to $7,695, depending on the property, location, and included features. HouseStay’s transparent pricing has catered to a wide range of budgets, offering flexible rental terms and detailed cost breakdowns to support the needs of digital nomads on the move.
You can explore cities nearby Winter Garden, like Clermont, Orlando, Four Corners, Reunion, and Kissimmee where similar monthly furnished rentals may be available. Check back soon—our listings are updated regularly, and Winter Garden continues to be a go-to city for remote work and temporary stays.
HouseStay Guarantee
We perform in-depth background checks on Host and Tenants to create a community everyone can trust.
Roommate Free
HouseStay only offers entire accommodations. We don’t offer spare rooms or shared spaces.
Fully Furnished
All accommodations listed on HouseStay are fully furnished and include all utilities in the monthly rate.
Month-to-Month Flexibility
Not sure how long you’ll be staying? All listings are available for a minimum of 30 nights with no maximum.
Winter Garden, Florida is a fantastic city to book an extended stay furnished rental, offering a multitude of benefits for various types of travelers. Families relocating to the area will appreciate the comfortable and convenient monthly short-term rentals available in neighborhoods such as Independence and Horizon West. Nearby cities like Orlando and Kissimmee offer a plethora of entertainment options, while top-rated schools like West Orange High School provide quality education for children.
For digital nomads seeking a temporary home base, Winter Garden’s month-to-month fully furnished rentals in the historic downtown area offer a charming and peaceful work environment. The proximity to popular museums like the Winter Garden Heritage Museum and fun activities like visiting nearby beaches make this city an inspiring place for remote work. Additionally, access to parks like Lake Apopka and shopping areas like Winter Garden Village at Fowler Groves provide plenty of opportunities for relaxation and downtime.
Vacationers will love staying in Winter Garden for its vibrant community and close proximity to Disney World and Universal Studios. Business travelers and interns will find the city to be an ideal location to book a temporary housing option near hospitals like AdventHealth Winter Garden and businesses in the area. Medical tourists coming into the city for surgeries or procedures can take advantage of the peaceful atmosphere and comfort of fully furnished rentals in Winter Garden.
Students attending local colleges or vocational schools, as well as travel nurses, sports professionals, and entertainment professionals working on productions in the area, will all find Winter Garden to be a welcoming and convenient city to book an extended stay furnished rental. Whether in need of insurance housing due to disaster recovery or simply looking for a temporary home away from home, Winter Garden has something to offer everyone seeking a comfortable and flexible living arrangement.