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Winter Springs, FL Homes for Rent with Pool

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  • /27

    $1,632 - $2,088 per month

    Legends Winter Springs

    1 - 3 Beds

    440 Courtney Springs Cir, Winter Springs, FL 32708

    Legends Winter Springs effortlessly combines exceptional service with outstanding features to provide the ultimate living experience. Located near upscale shopping and entertainment, your home is minutes to Lake Jessup and the excitement of downtown Orlando. Enjoy the peaceful, relaxing atmosphere of Legends Winter Springs. Please call for an appointment today.

    440 Courtney Springs Cir, Winter Springs, FL 32708
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    $2,300 per month

    • 3 Beds
    • 3 Baths
    • 1,447 Sq Ft
    • Townhouse for Rent

    600 Northern Way, Winter Springs, FL 32708

    Beautifully maintained townhouse tucked away in the exclusive, gated community of Tuscany Place. Step inside and feel the warmth of home as you're greeted by sleek ceramic tile floors flowing into a spacious open-concept kitchen and family room with granite countertops and modern stainless steel appliances. Upstairs, you’ll find two spacious bedrooms, EACH with their own private bathroom –

    Kathy Perez-Palacios DELTONA LAKES REALTY INC

    600 Northern Way, Winter Springs, FL 32708
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    $1,263 - $3,564 per month

    The Avenues at Winter Springs

    1 - 3 Beds

    1 Laurel Oaks Dr, Winter Springs, FL 32708

    Live Luxury The Avenues at Winter Springs offer a tranquil living experience in Winter Springs, FL, blending comfort, convenience, and affordability. Nestled in a serene residential area, residents enjoy peaceful surroundings while remaining conveniently close to Interstate 4 and the vibrant Uptown Altamonte Springs area. With easy access to shopping, dining, and entertainment options,

    1 Laurel Oaks Dr, Winter Springs, FL 32708
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    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,078 Sq Ft
    • Townhouse for Rent

    1450 Casa Park Cir, Winter Springs, FL 32708

    This newly renovated townhome is ready for new tenants! This townhome has 3 bedrooms, 2 bathrooms, a community pool, an in unit washer and dryer, and two assigned parking spaces. It is located in the desirable Tuscawilla neighborhood directly across from Trotwood park. Zoning for Seminole county schools is also a bonus. She is ready for lease today!

    Aileen MacDonald MACDONALD REALTY CORP

    1450 Casa Park Cir, Winter Springs, FL 32708
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    $1,600 - $2,740 per month

    RIZE at Winter Springs

    1 - 3 Beds

    150 Bear Springs Dr, Winter Springs, FL 32708

    RiZE at Winter Springs is a beautiful apartment community located in Winter Springs, Florida. Our convenient location provides easy access to fabulous shopping, fine dining, and ample entertainment to meet everyone's needs. Designed for comfort and luxurious hospitality, the upscale apartment homes at RiZE at Winter Springs offer gracious living in the northeastern portion of Orlando, Florida.

    150 Bear Springs Dr, Winter Springs, FL 32708
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    $2,400 per month

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft
    • Townhouse for Rent

    585 Cruz Bay Cir, Winter Springs, FL 32708

    Welcome to this pristine and beautifully designed townhome, nestled in the highly sought-after and gated community of The Landings at Parkstone. This charming 3-bedroom, 2.5-bathroom, two-story residence offers a spacious and open floor plan, featuring over 1,900 square feet of elegant living space that truly feels like a model home. Every corner of this home showcases designer touches

    Zane Place BLUE CHIP INTERNATIONAL REALTY LLC

    585 Cruz Bay Cir, Winter Springs, FL 32708
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    $1,238 - $1,939 per month

    Seville on the Green

    1 - 3 Beds

    300 Sheoah Blvd, Winter Springs, FL 32708

    Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

    300 Sheoah Blvd, Winter Springs, FL 32708
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    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 1,678 Sq Ft
    • Townhouse for Rent

    1382 Blumberg Blvd, Winter Springs, FL 32708

    Brand new 3 bed/2.5 bath Townhome with an extra large two car garage with park view in Winter Springs Town Center. Partially furnished (can be removed). You have to see it in person to appreciate the location. House comes with a top rated water filter and softner system. Extra large washer and dryer. This community also offers a pool. There are restaurants, grocery stores, Gyms, shops,

    Julia Martin JULIA MARTIN REALTY

    1382 Blumberg Blvd, Winter Springs, FL 32708
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    $1,174 - $1,799 per month

    Moss Park

    1 - 4 Beds

    170 N Gardenridge Ct, Winter Springs, FL 32708

    Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

    170 N Gardenridge Ct, Winter Springs, FL 32708
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    $1,850 per month

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft
    • Townhouse for Rent

    613 Casa Park Court B Ct N Unit B, Winter Springs, FL 32708

    Welcome to Casa Park Villas Community! This recently refreshed townhome is a gem with immaculate living spaces perfect for a family. Featuring 2 bedrooms and 2 bathrooms on the second floor, this home offers privacy and comfort. The main living area, kitchen, and dinette boast beautiful tiles, adding to the charm. Step outside to enjoy the gorgeous backyard and Florida living at its best.This

    John R. Gordon EXP REALTY LLC

    613 Casa Park Court B Ct N Unit B, Winter Springs, FL 32708
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    $1,679 - $3,523 per month

    Integra 360

    1 - 3 Beds

    1700 Integra Land Way, Winter Springs, FL 32708

    Discover modern luxury living at Integra 360, where elegant designs and upscale amenities await in our Winter Springs apartments. Choose from spacious one-, two-, or three-bedroom layouts, each adorned with premium features like table-sized kitchen islands, grand walk-in closets, and open-concept living spaces. Our pet-friendly community offers exclusive access to resort-style amenities,

    1700 Integra Land Way, Winter Springs, FL 32708
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    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 1,300 Sq Ft
    • Townhouse for Rent

    640 Macduff Ln Unit B, Winter Springs, FL 32708

    For Rent – Beautiful 3 Bedroom Home in Winter Springs!Welcome to 640 Macduff Ln, Unit B – a charming and updated 3-bedroom, 2-bathroom duplex located in the heart of Winter Springs. This spacious, single-story unit offers the perfect blend of comfort, privacy, and convenience.Home Features:3 spacious bedrooms with ample closet space2 full bathrooms with updated

    Emmanuella Richman CHARLES RUTENBERG REALTY ORLANDO

    640 Macduff Ln Unit B, Winter Springs, FL 32708
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    $1,360 - $2,126 per month

    Tuskawilla at Winter Springs

    1 - 3 Beds

    4545 Willa Creek Dr, Winter Springs, FL 32708

    We are now welcoming in-person, virtual and self-guided tours by appointment only. Please contact us today to schedule your appointment.Tuskawilla, Winter Springs, FL Apartments boast premier location great for both business and leisure. Located just minutes from SR417 and SR408, the Tuskawilla Apartments in Winter Springs are perfect for commuters all across Florida. Choose from a variety of

    4545 Willa Creek Dr, Winter Springs, FL 32708
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    $1,500 per month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    50 Moree Loop Unit 39, Winter Springs, FL 32708

    Dreams Do Come True!! Live your best life in this rarely available end-unit condo located in the vibrant, nature-rich Highlands—one of Central Florida’s most sought-after recreational communities! This freshly painted 2-bedroom, 1.5-bathroom two-story home offers comfort, style, and convenience, featuring tile floors throughout, ceiling fans in every room, and in-unit laundry. Both bedrooms are

    Freddie Crespo INVESTOR'S REAL ESTATE LLC

    50 Moree Loop Unit 39, Winter Springs, FL 32708
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    $1,800 per month

    • 2 Beds
    • 2 Baths
    • 1,359 Sq Ft
    • Townhouse for Rent

    505 Shadow Glen Place, Winter Springs, FL 32708

    Property Id: 1840361Welcome to a beautifully updated and meticulously maintained home with a truly worry-free and maintenance-free lifestyle. This exceptional property seamlessly blends modern updates with thoughtful community amenities, including grass cutting, common areas, garbage pickup, pool access, clubhouse, grilling area, picnic tables, two assigned parking spots, ample visitor

    505 Shadow Glen Place, Winter Springs, FL 32708
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    $1,900 per month

    • 2 Beds
    • 2.5 Baths
    • 1,275 Sq Ft
    • Townhouse for Rent

    197 Constitution Way, Winter Springs, FL 32708

    Available August 1, 2025 Stunning 2 Bedroom, 2.5 bath town-home with one car garage in Heritage Park (Gated Community). This residence offers an inviting open-concept floor plan on the main level, highlighted by wide plank rustic engineered hardwood flooring and a spectacular, unobstructed view of the natural spring located directly behind the property providing a tranquil and picturesque

    Leonardo Diaz ORLANDO PROP MGMNT RLTY LLC

    197 Constitution Way, Winter Springs, FL 32708
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    $1,900 per month

    • 2 Beds
    • 2.5 Baths
    • 1,156 Sq Ft
    • Townhouse for Rent

    613 Casa Park Ct N, Winter Springs, FL 32708

    Welcome to Casa Park Villas Community! This recently refreshed townhome is a gem with immaculate living spaces perfect for a family. Featuring 2 bedrooms and 2 bathrooms on the second floor, this home offers privacy and comfort. The main living area, kitchen, and dinette boast beautiful tiles, adding to the charm. Step outside to enjoy the gorgeous backyard and Florida living at its best. This

    613 Casa Park Ct N, Winter Springs, FL 32708
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    $1,600 per month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Condo for Rent

    230 Moree Loop Unit 3, Winter Springs, FL 32708

    Three bedroom/two bath home. Dining/living room combo with sliding glass doors that open to an enclosed screened balcony overlooking open green space in the community. Master bedroom has an En Suite. Community amenities included .

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    230 Moree Loop Unit 3, Winter Springs, FL 32708
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    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft
    • Townhouse for Rent

    452 Harbor Winds Ct, Winter Springs, FL 32708

    Welcome to 452 Harbor Winds Ct in the heart of Winter Springs! This spacious and well-maintained 3-bedroom, 2.5-bath townhome offers the perfect blend of comfort, style, and convenience. Step inside to an open-concept floor plan featuring a generous family room, dedicated dining area, and a cozy breakfast nook—ideal for both everyday living and entertaining. The kitchen flows seamlessly into the

    452 Harbor Winds Ct, Winter Springs, FL 32708
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    $1,500 per month

    • 2 Beds
    • 2 Baths
    • 972 Sq Ft
    • Condo for Rent

    10 Sheoah Blvd Unit 7, Winter Springs, FL 32708

    Spacious and bright 2 bedroom 2 bathroom condo for rent at The Highlands in Winter Springs. Just repainted throughout entire interior. Large family room with a small dining area. The two bedrooms on a split floor plan. The large master bedroom has sliding doors that lead to patio. The second, smaller, bedroom has its set of sliding doors leading to the screened-in porch and it's own bathroom.

    Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

    10 Sheoah Blvd Unit 7, Winter Springs, FL 32708
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    $1,860 - $3,060 per month

    Dwell Oviedo

    1 - 3 Beds

    500 Sugar Mill Rd, Oviedo, FL 32765

    500 Sugar Mill Rd, Oviedo, FL 32765
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    $2,699 per month

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft
    • House for Rent

    213 Gentle Breeze Ln, Casselberry, FL 32708

    Winter Springs Awesome House for Rent3 BEDROOMS AND 2.5 FULL BATHROOMS HOME IN TUSKAWILLA CROSSING !!! Available to move in. This home has an open floor plan; the Kitchen is loaded with upscale quartz countertops and GE stainless steel appliances. The master bathroom has dual sinks, a garden tub, and a walk-in shower. This family-friendly community, situated in Winter Springs’ highly

    Jaime Hernandez INTOP PROPERTY MANAGEMENT

    213 Gentle Breeze Ln, Casselberry, FL 32708
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    $10,000 per month

    • 4 Beds
    • 3 Baths
    • 3,790 Sq Ft
    • House for Rent

    610 Tina Ln, Winter Springs, FL 32708

    Available for lease. Welcome to 610 Tina Lane, a private five-acre equestrian estate with a remodeled 3,800-square-foot pool home with three-car garage on five acres and 2,500 square feet of fencing. This is a split-plan one-floor home with high ceilings throughout and porcelain Italian tile flooring. The kitchen boasts stainless steel appliances, a large kitchen island, wine refrigerator, Miele

    Andy Holland PREMIER SOTHEBY'S INTL. REALTY

    610 Tina Ln, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Townhouse for Rent

    208 Perth Ct Unit B, Winter Springs, FL 32708

    Highlights: 2 Car Garage | Spacious Backyard | Serene Patio | Community Pool | Nature Trails | BBQ Area Grills | Tennis Court | Community Playground | Picnic Area |Discover the vibrant charm of Winter Springs, nestled by the serene Lake Jesup and offering upscale living, diverse dining options, and a rich cultural scene. With pristine parks, top-notch schools, and annual festivities like

    Amy Johnston BELMONT REALTY

    208 Perth Ct Unit B, Winter Springs, FL 32708
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    $2,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,304 Sq Ft
    • Townhouse for Rent

    1622 Orrington Payne Place, Casselberry, FL 32707

    Welcome to your next home sweet home! This beautifully maintained 3-bedroom, 2.5-bathroom townhouse offers the perfect blend of comfort, style, and convenience. Nestled within a secure gated community, this two-story gem boasts an airy open floor plan with abundant natural light that fills the inviting living room and cozy dining area.The modern kitchen is a chef’s delight, featuring sleek

    Alison Ashby CORCORAN PREMIER REALTY

    1622 Orrington Payne Place, Casselberry, FL 32707
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    $2,350 per month

    • 3 Beds
    • 3.5 Baths
    • 1,405 Sq Ft
    • Townhouse for Rent

    1581 Orrington Payne Place, Casselberry, FL 32707

    This charming 3-bedroom, 2.5-bathroom townhome in the Winter Springs-Longwood area boasts spacious rooms, brand new flooring, and fresh interior paint throughout. Conveniently situated near shops, dining, and top-rated schools, this home offers easy access to everyday amenities. The property is only a 20-minute drive from downtown Orlando, making it ideal for commuters. Available for rent

    Frank Delesline, III LA ROSA REALTY SUCCESS LLC

    1581 Orrington Payne Place, Casselberry, FL 32707
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