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Houses for Rent in Highlands, Winter Springs, FL

Average rent

$2,200

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424 Club Dr - Photo 1 of 1

5d+ ago

Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

424 Club Dr, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Swimming pool

3 beds

2 baths

$2,000

House for rent

744 N Gretna Ct #NA - Photo 1 of 1

4d ago

Highlands house for rent in Winter Springs

$2,500 - 3 Bedroom 2 Bathroom House In Winter Springs With Great Amenities

744 N Gretna Ct #NA, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,500

House for rent

Available Apr 15

Description

Amazing 3-bedroom, 2-bathroom house in Winter Springs. Semi furnished. Amenities included: central air, central heat, dishwasher, stainless steel appliance, updated kitchen, washer dryer, laundry in building, and yard. No Utilities included. Is not pet friendly. Date Available: Apr 15th 2026. $2,500/month rent. $2,500 security deposit required. Please submit the form on this page or contact Daniela T at 321-318-8511 to learn more. This property is managed by a responsible landlord using Avail landlord software. Amazing 3 bedroom, 2 bathroom house in Winter Springs. Ameniti

863 Sheoah Cir - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

3 Bed, 2 Bath, Family Room, Comm Pool, & Fireplace!

863 Sheoah Cir, Winter Springs, FL 32708

Outdoor space | Garage parking | Swimming pool

3 beds

2 baths

$1,995

House for rent

Available Feb 1

451 Club Dr - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

451 Club Dr, Winter Springs, FL 32708

In-unit laundry | Swimming pool | Dishwasher

3 beds

2 baths

$2,150

$2,000

Price drop

House for rent

307 Montrose St - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

307 Montrose St, Winter Springs, FL 32708

On-site laundry | Outdoor space | Ceiling fan

3 beds

2 baths

$1,796

House for rent

Available Apr 3

542 Colonnades Cv - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2 beds

2 baths

$2,000

$1,690

Price drop

House for rent

Available May 1

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve this home for a $500 non-refundable holding fee until it's ready for move-in. This fee must be paid within 24 hours of being pre-qualified and will be applied to your first month’s rent if

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Nearby rental good for pet owners

709 Heather Ln - Photo 1 of 1

3d ago

Our team has verified this company

Verified

709 Heather Ln, Winter Springs, FL 32708

On-site laundry | Outdoor space | Storage

3 beds

2 baths

$2,315

House for rent

Available May 14

Description

We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

312 San Gabriel St - Photo 1 of 1

2d ago

House for rent in Winter Springs

312 San Gabriel St, Winter Springs, FL 32708

On-site laundry | Outdoor space | Storage

3 beds

2 baths

$2,095

$1,995

Price drop

House for rent

Available Mar 25

Description

Discover Deersong Single Family Home in Winter Springs, Fl: a refreshed 3-bedroom, 2-bath residence featuring brand new interior paint, blinds, stainless steel appliances and upgraded kitchen and bathroom cabinets. The home includes a fenced backyard and convenient exterior storage and residents have access to the community pool & Tennis Courts. Located within Seminole County Schools, this property offers modern finishes and low-maintenance outdoor space in a desirable neighborhood. This property offers an option of a security deposit-free lease using Obligo's billing auth

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775 Maple Leaf Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

775 Maple Leaf Loop, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Storage

4 beds

4.5 baths

$3,700

House for rent

Description

Property Status: Active Discover this stunning 4-bedroom + office/den home designed for comfort, efficiency, and modern living. Equipped with a solar energy system, you'll enjoy significantly reduced utility bills while being environmentally conscious. Upstairs features elegant, engineered wood flooring, while the garage includes its own air conditioning, perfect for a workshop, gym, or extra storage. The gourmet kitchen is a standout, offering an induction cooktop, double built-in ovens, spacious center island, and abundant cabinetry. The oversized owner's suite is a tr

775 Maple Leaf Loop #1 - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

Maple Leaf 775 - 1

775 Maple Leaf Loop #1, Winter Springs, FL 32708

Outdoor space | Swimming pool

4 beds

3.5 baths

$3,500

House for rent

Available Apr 8

Description

Discover this stunning 4-bedroom + office/den home designed for comfort, efficiency, and modern living. Equipped with a solar energy system, you'll enjoy significantly reduced utility bills while being environmentally conscious. Upstairs features elegant, engineered wood flooring, while the garage includes its own air conditioning, perfect for a workshop, gym, or extra storage. The gourmet kitchen is a standout, offering an induction cooktop, double built-in ovens, spacious center island, and abundant cabinetry. The oversized owner's suite is a true retreat, complete wit

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These rentals are 10%-30% cheaper than the local average price for similar rentals.

Listings within 5 miles
837 Shell Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

837 Shell Ln, Longwood, FL 32750

Outdoor space | Garage parking | High ceilings

3 beds

2 baths

$2,560

House for rent

Available May 27

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at rentprogress com smarthome Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and res

1819 Marley Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1819 Marley Pl Longwood, FL 32750

1819 Marley Pl, Longwood, FL 32750

Outdoor space | Garage parking | Fireplace

4 beds

2 baths

$2,585

House for rent

Available Apr 17

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2729.90. That covers your base rent, $2585.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. Who said the perfect house doesn't exi

585 Walden Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

585 Walden Ct, Winter Springs, FL 32708

On-site laundry | Swimming pool | On-site management

4 beds

3 baths

$2,855

House for rent

Available Jun 3

Description

We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

137 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

Garden 137

137 Garden Dr, Winter Springs, FL 32708

In-unit laundry | Carpet | Balcony

2 beds

1.5 baths

$1,800

$1,650

Price drop

House for rent

Available Apr 1

Description

This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day. Conveniently located near parks, shopping, dining, and top‑rated Seminole County schools, this home blends comfort, convenience, and community living. Contact Florida Rental Team for you

137 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

2 beds

2 baths

$1,800

$1,650

Price drop

House for rent

Description

This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day. Conveniently located near parks, shopping, dining, and top‑rated Seminole County schools, this home blends comfort, convenience, and community living. Contact Florida Rental Team for you

133 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

2 beds

1.5 baths

$1,800

$1,650

Price drop

House for rent

Description

This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day. Conveniently located near parks, shopping, dining, and top‑rated Seminole County schools, this home blends comfort, convenience, and community living. Contact Florida Rental Team for you

537 Sunbranch Ln - Photo 1 of 1

5d+ ago

House for rent in Casselberry

537 Sunbranch Ln, Casselberry, FL 32707

Dishwasher | Oven | Microwave

3 beds

2.5 baths

$2,550

House for rent

Description

Welcome to this inviting 3-bedroom, 2.5-bathroom home located in the heart of Casselberry. Nestled in a charming, quiet neighborhood, this property offers comfort, convenience, and a great location. Enjoy being within walking distance to Foxtail Coffee Co. and just minutes from everyday essentials like Publix, with quick access to 434 and the 417 for an easy commute throughout Central Florida. The home features a functional layout with spacious living areas, comfortable bedrooms, and a well-designed floor plan suited for both relaxing and entertaining. Tthis is a great opp

132 Sundance Ct - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

132 Sundance Ct, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$1,985

House for rent

Description

Property Status: Active Beautiful 3-bedroom, 2-bath home located in the desirable Seasons at Mt. Greenwood community in Winter Springs. Offering 1,161 sq. ft. of living space, this well-maintained home features a freshly painted interior, granite countertops, rich cherrywood cabinetry, recessed lighting, and vaulted ceilings with a skylight that fills the great room with natural light. Enjoy relaxing on the spacious screened porch overlooking private conservation views. Additional highlights include 2” blinds, ceiling fans throughout, and a single-car garage. Residents hav

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207 S Moss Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

207 S Moss Rd, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Ceiling fan

2 beds

1.5 baths

$1,495

House for rent

Description

Property Status: Pending 2BD/1.5BA home for rent in Winter Springs on S Moss Rd. Features a bright, functional layout, spacious living area, kitchen with ample cabinet space, and well-sized bedrooms. Large yard for outdoor use. Conveniently located near parks, shopping, dining, SR-434, I-4, and Seminole County schools. Office Phone: (407) 829-2418 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

509 Sunbranch Ln - Photo 1 of 1

5d+ ago

House for rent in Casselberry

509 Sunbranch Ln, Casselberry, FL 32707

Dishwasher | Microwave | Oven

4 beds

3.5 baths

$2,725

House for rent

Description

Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom two-story home located in the heart of Casselberry. Built in 2021, this newer construction offers modern finishes, thoughtful design, and plenty of space for comfortable living. Situated in a charming, quiet neighborhood, the home is conveniently within walking distance to Foxtail Coffee Co. and just minutes from shopping and dining like Publix, with easy access to 434 and the 417. Inside, you’ll find spacious living areas, a functional two-story layout, and generously sized bedrooms. This property combines mod

544 Tall Oaks Ter - Photo 1 of 1

5d+ ago

House for rent in Longwood

3 beds

2 baths

$2,325

House for rent

Description

3/2, 2 Car Garage, Single Family Home, Living Room and Dining Room Combo, Family Room, Eat-In Kitchen, Kitchen Appliances Included: Stove, Refrigerator, Disposal and Dishwasher, Kitchen Laundry with Washer and Dryer Included, Laminate Wood and Carpet Throughout Home, Master Bathroom has Dual Sinks and separate Garden Tub and Shower, Vaulted Ceilings, Walk-In Closets, Sprinkler System, Open Patio, Partially Fenced Backyard, Community Tennis and Playground, Pest Control Included by Owner, Dogs Ok - NO CATS, NO SMOKING, Year Built: 1995/ 1601 Sqft. Directions: I-4 WEST: Take

402 E Springtree Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

402 E Springtree Way, Lake Mary, FL 32746

On-site laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,250

House for rent

Available Feb 11

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Rent this home by April 30, 2026 and receive $500 Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and connected. Homes like this don’t stay on the market for long—don’t miss your chance to make it yours. Apply today! The Homeowners Assoc

337 Riunite Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

337 Riunite Cir, Winter Springs, FL 32708

Outdoor space | Garage parking | High ceilings

3 beds

2 baths

$2,555

House for rent

Available Jun 16

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at rentprogress com smarthome Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and res

362 Cidermill Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

362 Cidermill Pl Lake Mary, FL 32746

362 Cidermill Pl, Lake Mary, FL 32746

Outdoor space | Garage parking | Fireplace

3 beds

2.5 baths

$2,499

House for rent

Available Mar 25

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2643.90. That covers your base rent, $2499.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. You deserve a quality home that you ca

577 Remington Oak Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

577 Remington Oak Dr Lake Mary, FL 32746

577 Remington Oak Dr, Lake Mary, FL 32746

Outdoor space | Garage parking | Fireplace

3 beds

2 baths

$2,535

House for rent

Available Apr 7

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2679.90. That covers your base rent, $2535.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. This is the house you've been searchin

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Springs > Highlands Houses For Rent
Updated: April 19, 2026

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Discover houses for rent in Highlands, Winter Springs, FL

🌇Available house rentals25 houses
💰Best rent deal542 Colonnades Cv
🍃With outdoor space
Popular amenities, ,
👚With laundry facilities
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos