
Cheap Homes for Rent in Deer Island Neighborhood of Winter Garden, FL from $1,900 (10 Rentals)
Search the lowest-cost Homes available for rent right now in the Deer Island area of Winter Garden.


1532 Broken Oak Dr

4432 Barbados Loop

1500 Broken Oak Dr

15643 Charter Oaks Trail
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

1543 Tiverton Blvd

4476 Barbados Loop

1647 Portcastle Cir

3677 Serena Ln

17522 Promenade Dr
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
Deer Island, Winter Garden, FL Local Guide

How much does it cost to rent a home in Deer Island?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Deer Island 3 Bedroom Homes for Rent | $2,503 | $1,999 | $3,500 |
| Deer Island 4 Bedroom Homes for Rent | $3,695 | $2,400 | $9,500 |
| Deer Island 5 Bedroom Homes for Rent | $5,863 | $2,895 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 10 rentals with your search options within a 3 mile radius of the Deer Island Neighborhood of Winter Garden, FL.
Explore Winter Garden
Cheapest Available Deer Island Apartments for Rent
 The cheapest available apartment rental in the Deer Island area of Orlando, FL is a Studio unit found at Winterwoods priced from $1,099. Inland Seas Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,210. Here are the most affordable Deer Island apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Winterwoods | Studio Apartment | Studio,1BA | $1,099 |
| Inland Seas Apartments | One Bed/ One Bath | 1BR,1BA | $1,210 |
| AVENUE ON OAKLAND | S1 (Colonial) | Studio,1BA | $1,537 |
Best Value Apartments for Rent in Deer Island, FL
As of January 03, 2026 the best value apartment in the Deer Island area is the $1.55 price per square foot 1500 Broken Oaks Drive Model at 1500 Broken Oaks Drive, Unit 25B in the in the Deer Island neighborhood starting from $2,400. The second greatest value Deer Island apartment is the Honey Bell Model at Advenir at Castle Hill starting at $1,824 with a $1.82 price per square foot in the Lincoln Park neighborhood. Here is today’s list of the best values for Deer Island apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 1500 Broken Oaks Drive, Unit 25B | 1500 Broken Oaks Drive | 3BR,2.5BA | $1.55 |
| Advenir at Castle Hill | Honey Bell | 1BR,1BA | $1.82 |
| 724 Lake Brim Dr, Unit Mother-In-Law Suite | 724 Lake Brim Dr | 1BR,1BA | $1.76 |
| Country Gardens | Two Bedroom Two Bath | 2BR,2BA | $1.84 |
| Skyline at Westfall Station | A3 | 1BR,1BA | $2.26 |
| Broadstone Overlands | A1 | 1BR,1BA | $2.77 |
| Inland Seas Apartments | One Bed/ One Bath | 1BR,1BA | $2.16 |
| AVENUE ON OAKLAND | S1 (Colonial) | Studio ,1BA | $3.13 |
| Winterwoods | Studio Apartment | Studio ,1BA | $3.82 |
Frequently Asked Questions about Deer Island
What type of rentals are currently available in Deer Island?
There are currently 12 Apartments for Rent in Deer Island, FL with pricing that ranges from $1,099 to $4,454. There are also 61 Single Family Homes for rent, Condos, and Townhome rentals currently available in Deer Island ranging from $1,999 to $18,000.
What is the current price range for Rental Homes in Deer Island?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Deer Island ranges from $1,999 to $18,000 with an average monthly rent of $4,020.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Helpful Local Expert Guides

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla Ferrara
For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

Your Guide to the Perfect Orlando Neighborhood for Student Renters
Written by: Darla Ferrara
There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
Written by: Darla Ferrara
When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

The Soul of the City Beautiful: What Life in Orlando Is Really Like
Written by: Darla Ferrara
When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.
Articles, How-To's, and Tips

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!