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Houses for Rent in Highlands, Winter Springs, FL

Average rent

$2,000

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651 Macduff Ln Apt B #Apt B - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

651 Macduff Ln Apt B #Apt B, Winter Springs, FL 32708

Outdoor space | Garage parking | Carpet

3 beds

2 baths

$1,950

House for rent

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

302 Bridie Ct - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

302 Bridie Ct, Winter Springs, FL 32708

Swimming pool | Residents lounge

3 beds

2 baths

$2,450

House for rent

647 Redwood Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

House for rent

Available Nov 21

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

420 San Gabriel St #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

420 San Gabriel St #NA, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Storage

2 beds

1 bath

$1,850

House for rent

Available Oct 14

Description

Welcome to this nice and quiet neighborhood! Enjoy this recently renovated home. Freshly painted. New tiles. Stainless steel appliances. New A/C. Relax with friends and family in the patio. Outside Storage Room. Zoned for Seminole County Public Schools and only minutes from Winter Springs Town Center, Seminole State College, major highways, hospitals, and many good places to eat. No Pets Allowed, Renter pays all Utilities, No Smoking inside the Property. Renter is responsible for changing AC filter and keep dryer filter clean. One parking is assigned to renter.

102 Kristi Ann Ct - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Springs

House for rent

Description

Charming two-story townhome available for rent in Winter Springs in the Moss Cove Townhome Community. This home offers two spacious bedrooms and one and a half bathrooms, with the kitchen and bathrooms recently remodeled for a fresh, modern feel. Located in a small, quiet neighborhood, the property provides a peaceful living environment while still being conveniently close to 1792, 434, Highway 417 and I-4, making commuting simple and efficient in any direction. This is a wonderful opportunity to enjoy comfort and convenience in a desirable location. Please call or email

Nearby rental good for eco-living

Nearby rental good for pet owners

40 N Fairfax Ave - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

40 N Fairfax Ave

40 N Fairfax Ave, Winter Springs, FL 32708

In-unit laundry | Air conditioning

2 beds

1 bath

$1,600

House for rent

Description

Welcome to this clean and inviting 2-bedroom, 1.5-bath home in the heart of Winter Springs. Enjoy a comfortable layout and a convenient location close to shopping, dining, and beautiful local parks. With easy access to major highways, commuting to Orlando is a breeze. Perfect for anyone looking for a relaxed lifestyle with everything nearby!

122 Lori Anne Ln - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

House for rent

Description

Welcome to 122 Lori Anne Ln, a home that redefines what it means to live in serenity, style, and sophistication. Tucked away in the heart of Seminole County, this remarkable residence seamlessly blends modern design with warm touches of comfort, creating an inviting sanctuary for families and individuals alike. Every detail, from the expansive floor plan to the thoughtfully designed finishes, reflects a commitment to quality living. Step inside and be greeted by soaring ceilings and a flood of natural light that illuminates every corner of the home. The spacious open-conc

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276 San Gabriel St - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

276 San Gabriel St, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$1,850

House for rent

Description

Property Status: Pending Don't look further!! This house is 3/2 with upgraded kitchen and in doors laundry closet make it good for your family daily needs, fenced backyard with storage closet. A+ rated Seminole county public schools, also you will enjoy your weekends and free time either at the gated community swimming pool or at Torcaso Park. Ready for Rent, Schedule your showing today!! Office Phone: (407) 545-6430 Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be

326 San Rafael St - Photo 1 of 1
No deposit

5d+ ago

House for rent in Winter Springs

326 San Rafael St, Winter Springs, FL 32708

In-unit laundry | Swimming pool | Ceiling fan

1 bed

1 bath

$1,400

House for rent

Description

Super cute, 1 bed/1 bath villa with an enclosed porch to enjoy year round. Laminate and tile flooring in living areas and carpet in the bedroom. Washer and dryer included, small fenced area and a shed. Conveniently located. Call today! ONLY apply via CFRP. com not any other site EQUAL HOUSING OPPORTUNITY C F R P Realty is proud to offer no deposit move-ins to qualified renters through Obligo! We understand that moving costs can add up, so we want to extend financial flexibility to our residents. When you move in with us, you can skip paying a security deposit and keep t

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309 San Gabriel St - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

309 San Gabriel St, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$1,995

House for rent

Description

Property Status: Active Updated Top to Bottom, this 3 Bedroom, 2 Bath Boasts NEW Cabinets, NEW Flooring, NEW Upgraded Appliances Including Washer/Dryer & Microwave. Also Includes a Screen Porch, Fenced Pavered Courtyard, Storage Shed, & Community Pool. Office Phone: (407) 324-9182 Copyright © 2025 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.

705 Woodlawn Dr - Photo 1 of 1
Rent special

3d ago

House for rent in Winter Springs

3 Bedroom Pet-Friendly Home in Winter Springs, FL with Main Street Renewal

705 Woodlawn Dr, Winter Springs, FL 32708

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$1,975

House for rent

Description

Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technology

181 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

181 Garden Dr, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Carpet

2 beds

1 bath

$1,200

House for rent

Description

Property Status: Active 181 Garden Dr. Winter Springs - Two story townhouse with two bedroom 1 1/2 bath, all bedrooms upstairs. Large back & Front yard. Minutes away from 17-92 and SR 417. Office Phone: (407) 673-1400 Copyright © 2025 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.

Listings within 5 miles
1968 Downs Ct - Photo 1 of 1

4d ago

Our team has verified this company

Verified

1968 Downs Ct, Lake Mary, FL 32746

On-site laundry | Outdoor space | Garage parking

4 beds

3 baths

$3,080

House for rent

Available Nov 25

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

805 Lewis Pl - Photo 1 of 1

5d+ ago

House for rent in Longwood

Single Family Residence - LONGWOOD, FL

805 Lewis Pl, Longwood, FL 32750

In-unit laundry | Outdoor space | Garage parking

4 beds

2 baths

$2,850

House for rent

Description

Property Status: Active Set on a large corner lot in the sought-after Chelsea Place community, this four-bedroom home offers a bright, open layout designed for comfort and convenience. High ceilings, natural light, and a versatile split-bedroom floor plan create the perfect balance between privacy and shared living. The kitchen with breakfast nook flows seamlessly into the family room and includes modern appliances along with a built-in stereo system with speakers throughout the home. The primary suite features a walk-in closet, an en suite bath with jetted tub, and slidi

914 Osceola Trl - Photo 1 of 1

5d+ ago

House for rent in Casselberry

914 Osceola Trl, Casselberry, FL 32707

On-site laundry | Assigned parking | Air conditioning

3 beds

2 baths

$2,000

House for rent

Description

Welcome to your new home on Lake Hodge in Casselberry, FL! This inviting property offers a fantastic opportunity for comfortable living in a vibrant neighborhood. There is a neighborhood fishing dock, playground and basketball court at the end of the street. The fenced yard and screened porch have sunset views of Lake Hodge. With nearby dining options and stores, convenience is at your doorstep. AdventHealth Altamonte Springs is just a short 16-minute drive away, making it easy to access quality healthcare. Key features of this property include spacious living areas desi

1260 Seminola Blvd #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

RARE RENT-TO-OWN OPPORTUNITY WITH SPECIAL OFFICE/RESIDENTIAL ZONING! (Grandfathered-In)

1260 Seminola Blvd #NA, Casselberry, FL 32707

In-unit laundry | Outdoor space | Assigned parking

3 beds

2 baths

$2,500

House for rent

Available Sep 12

Description

Imagine having the convenience of living and work from home in the same location. This move-in ready completely renovated LAKEFRONT POOL property has so much flexibility. Special grandfathered-in zoning provides endless opportunities, featuring 3 rooms and 2 full bathrooms that could actually be split into 2 separate rentable spaces. This allows you to reside on half of the property and lock-off the other half (with separate entrance) to be utilized for business purposes, such as a Law or CPA office, or the newly added Medical use. With so much to love, this property won't

1978 Fireside Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1978 Fireside Ct Casselberry, FL 32707

1978 Fireside Ct, Casselberry, FL 32707

Outdoor space | Garage parking

3 beds

2 baths

$2,375

House for rent

Available Oct 23

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 $2519.90. That covers your base rent, $2375.00 + 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. Currently being refreshed by Invitatio

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633 Alton Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

633 Alton Rd Winter Springs, FL 32708

633 Alton Rd, Winter Springs, FL 32708

Outdoor space | Garage parking

3 beds

2 baths

$2,085

House for rent

Available Aug 29

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 $2229.90. That covers your base rent, $2085.00 + 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. $1000 off first full month's rent with

403 Cidermill Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

403 Cidermill Pl Lake Mary, FL 32746

403 Cidermill Pl, Lake Mary, FL 32746

Outdoor space | Garage parking | High ceilings

3 beds

2 baths

$2,160

House for rent

Available Sep 10

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 $2304.90. That covers your base rent, $2160.00 + 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. $1000 off first full month's rent with

1260 Seminola Boulevard - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1260 Seminola Boulevard, Casselberry, FL 32707

In-unit laundry | Storage | Air conditioning

3 beds

2 baths

$2,500

House for rent

Available Sep 11

Description

RARE RENT-TO-OWN OPPORTUNITY WITH SPECIAL OFFICE/RESIDENTIAL ZONING! (Grandfathered-In) Imagine having the convenience of living and working in the same location. This move-in ready completely renovated LAKEFRONT POOL property sitting on .32 acres has so much flexibility. Special grandfathered-in zoning provides endless opportunities, featuring 3 rooms and 2 full bathrooms that could actually be split into 2 separate rentable spaces. This allows you to reside on half of the property and lock-off the other half (with separate entrance) to be utilized for business purposes,

473 E Jessup Ave - Photo 1 of 1

5d+ ago

House for rent in Longwood

2 beds

2 baths

$1,300

House for rent

Description

This 2 bedroom, 2 bathroom duplex offers 960 sq. ft. of living space in a convenient Longwood location. Just off East State Road 434 & North US Hwy 17-92, you’ll be close to shopping, dining, and Orlando Health ER. The home features tile flooring throughout, washer/dryer hookups, and a functional layout. A screened-in back porch and fenced yard provide outdoor space to enjoy, while the private driveway adds everyday convenience. Located in Seminole County with no HOA restrictions, this rental provides comfort and value in a prime spot. Renters Insurance Required DISCLAIM

268 Frances Ave #B - Photo 1 of 1

5d+ ago

House for rent in Casselberry

1 bed

1 bath

$1,325

House for rent

Description

Discover this beautifully updated 1 bed, 1 bath home in the sought-after community of Casselberry, FL. Featuring brand-new flooring for a fresh, modern look and a fully upgraded kitchen with new appliances and cabinets, this home offers both style and functionality. The open floor plan creates a spacious, inviting atmosphere, while the private patio is perfect for enjoying Florida’s sunshine. Best of all, utilities and trash service are included—adding exceptional value to this already amazing find. Conveniently located near shops, dining, and local attractions, this home

241 Ruth Blvd - Photo 1 of 1

2d ago

House for rent in Longwood

241 Ruth Blvd, Longwood, FL 32750

In-unit laundry | Garage parking

1 bed

1 bath

$1,100

House for rent

Description

Property Status: Active Beautiful 1 bedroom 1 bath in the heart of Longwood! Unit has new paint and new flooring. Rent includes all utilities and internet. Washer & Dryer are shared in a common area space. Cats accepted! Office Phone: (407) 725-9660 Copyright © 2025 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.

1314 Tarflower Dr - Photo 1 of 1
New construction

5d+ ago

Townhouse for rent in Winter Springs

1314 Tarflower Dr, Winter Springs, FL 32708

In-unit laundry | Storage | Garage parking

3 beds

2 baths

$2,750

House for rent

Description

Property Status: Active Spacious 3-Bedroom Townhome for Rent – Prime Location! Brand new Spacious 3 Bedroom 2.5 bath two-story townhome in the upscale community of Hickory Grove in Winter Springs features an open-concept layout with high-end finishes, upgraded flooring, and stylish fixtures throughout. Hardwood looking ceramic tiles throughout the first floor with modern kitchen, quartz countertops and stainless steel appliances. Upstairs are all three bedrooms, including the spacious primary suite featuring a private en-suite bathroom with dual vanity and a walk-in cl

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Springs > Highlands Houses For Rent
Updated: October 21, 2025

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Discover houses for rent in Highlands, Winter Springs, FL

🌇Available house rentals25 houses
💰Best rent deal181 Garden Dr
🍃With outdoor space
Popular amenities, ,
🍽With dishwasher
🚗With garage parking
🏠With photos