Winter Garden

Orange County, Florida

Renting in Winter Garden

Winter Garden is an Orange County market with 169 active rentals on the market today, ranging from $1,399 to $8,000 per month.

The shape of the market is measurable: the mix leans toward single-family homes and townhomes, and three-bedroom and four-bedroom homes account for most of what is listed right now. Listings currently active here have spent an average of 31 days on the market.

Every matching Winter Garden rental is in reach, whichever brokerage lists it, because NAH Rental Homes represents renters across the full Stellar MLS. Describe the home you want at TenantMatch and it builds the search for you.

Single-Family HomesCondosTownhomesHomes with a PoolNew Construction HomesLuxury Rentals

Winter Garden Market Snapshot

$2,995/mo
Median Rent
31 days
Avg Days on Market
169
Active Listings
2026-10-05
Last Updated

Live count from the current MLS rental feed; figures update as inventory changes.

Available Rentals in Winter Garden

Showing 24 of 169 active rentals in Winter Garden.

View all 169 rentals in Winter Garden

Winter Garden Map

Winter Garden Rental Questions

How does renting in Winter Garden work?
It works in three steps: you define what you want, tour the Orange County rentals that match, and have NAH Rental Homes represent you through application and lease.
What does it cost to rent in Winter Garden?
The live feed answers this best: 169 active rentals in Winter Garden, ranging from $1,399 to $8,000 per month. A static average would hide how much the property type and size move the number.
What does the Winter Garden rental mix look like?
The mix leans toward single-family homes and townhomes, and three-bedroom and four-bedroom homes make up most of the current availability. The mix shifts as listings turn over, so a live search reflects it best.
Does NAH Rental Homes charge renters a fee in Winter Garden?
NAH Rental Homes represents renters across the full Stellar MLS in Winter Garden, and any renter-side terms are set out in writing in your tenant representation agreement before you tour. You see every matching rental, NAH-managed or not, with no ranking tricks and no surprise charges.
How do I start a rental search in Winter Garden?
Start with TenantMatch, our intelligent intake at /tenantmatch. You describe the home you want in your own words, and it builds a precise Winter Garden rental search, ranks the closest matches, and flags new listings as they appear.

Looking to rent in Winter Garden?

Whether you are starting your search or ready to tour, our team brings local market knowledge and tech-forward workflows to every move.

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