
Cheap Homes for Rent in Sleepy Hollow Neighborhood of Leesburg, FL from $1,100 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Sleepy Hollow area of Leesburg.


33305 Ryan Dr

33305 Ryan Dr

2630 Icabod Ct
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.

1306 Shady Terrace

33424 Shady Acres Rd

2602 Icabod Ct

2609 Hollow Ln
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.

2610 Icabod Ct
Sleepy Hollow, Leesburg, FL Local Guide

How much does it cost to rent a home in Sleepy Hollow?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Sleepy Hollow 2 Bedroom Homes for Rent | $1,412 | $1,250 | $1,575 |
| Sleepy Hollow 3 Bedroom Homes for Rent | $1,865 | $1,100 | $2,510 |
| Sleepy Hollow 4 Bedroom Homes for Rent | $2,206 | $2,045 | $2,400 |
| Sleepy Hollow 5 Bedroom Homes for Rent | $2,360 | $2,315 | $2,450 |
Browse Homes for Rent in this Neighborhood
There are currently 9 rentals with your search options within a 3 mile radius of the Sleepy Hollow Neighborhood of Leesburg, FL.
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Sleepy Hollow, Leesburg, FL Local Guide
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Cheapest Available Sleepy Hollow Apartments for Rent
 The cheapest available apartment rental in the Sleepy Hollow area of Leesburg, FL is a 1 Bed unit found at Arbours at Silver Lake priced from $1,075. Lake Harris Cove has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,123. Here are the most affordable Sleepy Hollow apartments for rent in Leesburg, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Arbours at Silver Lake | ONE BEDROOM | 1BR,1BA | $1,075 |
| Lake Harris Cove | One Bedroom One Bath (b) | 1BR,1BA | $1,123 |
| Blueberry Hill | One Bed One Bath Standard | 1BR,1BA | $1,200 |
Best Value Apartments for Rent in Sleepy Hollow, FL
As of February 26, 2026 the best value apartment in the Sleepy Hollow area is the $1.11 price per square foot Four Bedroom Three Bath Model at Harbor Vista in the in the Silver Lake Estates neighborhood starting from $2,045. The second greatest value Sleepy Hollow apartment is the 2bedroom/2bathroom Model at Laurel Oaks starting at $1,223 with a $1.18 price per square foot in the Silver Lake Estates neighborhood. Here is today’s list of the best values for Sleepy Hollow apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Harbor Vista | Four Bedroom Three Bath | 4BR,3BA | $1.11 |
| Laurel Oaks | 2bedroom/2bathroom | 2BR,2BA | $1.18 |
| Integra Isles | A1 | 1BR,1BA | $1.63 |
| Arbours at Silver Lake | ONE BEDROOM | 1BR,1BA | $1.29 |
| 310 W Dixie Ave, Unit 4 | 310 W Dixie Ave | 1BR,1BA | $1.68 |
| Lake Harris Cove | One Bedroom One Bath | 1BR,1BA | $1.94 |
| Blueberry Hill | One Bed One Bath Standard | 1BR,1BA | $2.10 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Pet Friendly LifestyleSleepy Hollow, Leesburg, FL
Ranked #1
Among cities in Florida for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Frequently Asked Questions about Sleepy Hollow
What type of rentals are currently available in Sleepy Hollow?
There are currently 44 Apartments for Rent in Sleepy Hollow, FL with pricing that ranges from $929 to $2,239. There are also 27 Single Family Homes for rent, Condos, and Townhome rentals currently available in Sleepy Hollow ranging from $1,100 to $2,510.
What is the current price range for Rental Homes in Sleepy Hollow?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Sleepy Hollow ranges from $1,100 to $2,510 with an average monthly rent of $1,711.
How much are larger Three and Four Bedroom Rentals in Sleepy Hollow?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Sleepy Hollow range from $1,397 to $2,239, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,100 to $2,510. Four Bedroom Single-Family rentals are also available starting from $2,045 and Four Bedroom Apartments start at $1,519.
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.
Articles, How-To's, and Tips

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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.