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Rent Specials
$1,174 - $1,8141 to 2 Bedroom Apartments Available Now
Chesapeake
2307 Cumberland CirClearwater, FL 33763
Cheap Apartments for Rent in the Winding Wood Neighborhood of Tampa, FL from $1,100 (20 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winding Wood area of Tampa.
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$1,414 - $3,9491 to 3 Bedroom Apartments Available Now
Peninsula at Northwood
2690 Enterprise Rd EClearwater, FL 33759
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$1,779 - $2,7441 to 3 Bedroom Apartments Available Sep 15
The Palms @ Chesapeake
3500 Burlingame CirClearwater, FL 33763
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$1,690 - $3,0101 to 3 Bedroom Apartments Available Now
The Alexander at Countryside
2524 Alexander PlClearwater, FL 33763
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$1,199 - $2,409Studio to 3 Bedroom Apartments Available Now
The Palms at Countryside Apartments
25350 US Highway 19 NClearwater, FL 33763
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$1,482 - $1,992
Total Monthly Price
1 to 3 Bedroom Apartments Available NowTotal Monthly Price
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$1,482 - $1,992
Total Monthly Price
$1,482 - $1,992
Estates at Countryside
2652 N McMullen Booth RdClearwater, FL 33761
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From budget-friendly East Tampa to the trendy Channel District, where you live in Tampa makes a big difference in what you pay. Get our local expert's complete cost of living breakdown before you make your move.
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1 Bedroom Apartments
Inverness Condominiums
2579-2599 Countryside BlvdClearwater, FL 33761
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Studio Apartments
The Fountains At Countryside
2500 Winding Creek BlvdClearwater, FL 33761
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2 to 3 Bedroom Apartments
Regency Heights
2550 Florida 580Clearwater, FL 33761
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2 Bedroom Apartments
1000-1040 Creek Park Dr
1000-1040 Creek Park DrDunedin, FL 34698
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2 Bedroom Apartments
1850-1870 Main St
1850-1870 Main StSafety Harbor, FL 34695
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Studio Apartments
Countryside Estates Mobile Home Park
27466 US Highway 19 NClearwater, FL 33761
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
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Studio Apartments
Riveria Mobile Home Estates
29141 US Highway 19 NClearwater, FL 33761
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3 Bedroom Apartments
Europa of Countryside Condominiums
2632 Enterprise RD EClearwater, FL 33759
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1 Bedroom Apartments
Amber Glades Manufactured Housing
3113 State Road 580Safety Harbor, FL 34695
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1 to 2 Bedroom Apartments
Bryn Mawr At Countryside Condos
2737 Countryside BLVDClearwater, FL 33761
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2 Bedroom Apartments
Misty Springs Condos
2677 Sabal Springs CIRClearwater, FL 33761
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1 Bedroom Apartments
Bays End Manor Manufactured Housing
3432 State Road 580Safety Harbor, FL 34695
Tampa Has It All: The Ultimate Insider's Guide to Things to Do in Tampa
From Busch Gardens to Ybor City, Tampa has something for everyone. Our local expert breaks down the best things to do across every region of the city — parks, dining, nightlife, and more.
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Windsor Clearwater
2031 Glass LoopClearwater, FL 33763
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2 Bedroom Apartments
640 2nd St N
640 2nd St NSafety Harbor, FL 34695
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Winding Wood, Tampa, FL Local Guide
How much does it cost to rent an apartment in Winding Wood?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winding Wood Studio Apartments | $1,199 | $1,199 | $1,199 |
| Winding Wood 1 Bedroom Apartments | $1,554 | $1,319 | $1,969 |
| Winding Wood 2 Bedroom Apartments | $1,872 | $1,450 | $2,365 |
| Winding Wood 3 Bedroom Apartments | $2,323 | $1,812 | $3,949 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 20 rentals with your search options within a 2 mile radius of the Winding Wood Neighborhood of Tampa, FL.
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Winding Wood, Tampa, FL Local Guide
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Cheapest Available Winding Wood Apartments for Rent
The cheapest available apartment rental in the Winding Wood area of Tampa, FL is a Studio unit found at The Palms at Countryside Apartments priced from $1,199. Chesapeake has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,399. Here are the most affordable Winding Wood apartments for rent in Tampa, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Palms at Countryside Apartments | E1-Serendipity | Studio,1BA | $1,199 |
| Chesapeake | 1M1 - 1 Bdrm, 1 Bath-MED | 1BR,1BA | $1,399 |
| Estates at Countryside | 1x1A | 1BR,1BA | $1,482 |
| Contempo Lane | 2 bedroom 2 bath with 1000 sf | 2BR,2BA | $1,660 |
| Peninsula at Northwood | A3 | 1BR,1BA | $1,684 |
Best Value Apartments for Rent in Winding Wood, FL
As of August 18, 2026 the best value apartment in the Winding Wood area is the $1.68 price per square foot 3 bedroom 2 bath with 1200 sf Model at Contempo Lane in the in the Downtown Dunedin neighborhood starting from $2,010. The second greatest value Winding Wood apartment is the B2 Model at Peninsula at Northwood starting at $2,173 with a $1.81 price per square foot in the Bridgeport neighborhood. Here is today’s list of the best values for Winding Wood apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Contempo Lane | 3 bedroom 2 bath with 1200 sf | 3BR,2BA | $1.68 |
| Peninsula at Northwood | B2 | 2BR,2BA | $1.81 |
| The Alexander at Countryside | A1D | 1BR,1BA | $2.07 |
| Windsor Clearwater | A1 | 1BR,1BA | $2.57 |
| Estates at Countryside | 1x1A | 1BR,1BA | $2.09 |
| Chesapeake | 1M1 - 1 Bdrm, 1 Bath-MED | 1BR,1BA | $2.11 |
| The Palms at Countryside Apartments | E1-Serendipity | Studio ,1BA | $2.40 |
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.
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Top Student Friendly Neighborhoods to Rent Near Colleges in Tampa
A Local Expert's guide to the Best Student Friendly Neighborhoods Near Colleges in the Tampa Bay area for affordable living. Find your perfect Tampa Student apartment, condo, or rental home today at ApartmentHomeliving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Best Local Schools in Winding Wood, Tampa, FL
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Frequently Asked Questions about Cheap Winding Wood Apartments
How much is rent for a Cheap One Bedroom Winding Wood Apartment?
The lowest price for a Cheap One Bedroom Winding Wood Apartment is $1,319 at The Palms at Countryside Apartments.
What is the lowest price for a Cheap Two Bedroom Winding Wood Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winding Wood is starting from $1,579 at The Palms at Countryside Apartments.
What is the most affordable Winding Wood Three Bedroom Apartment?
The best deal on a cheap Winding Wood Three Bedroom Apartment rental is at Estates at Countryside and starts from $1,905.
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.
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