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Houses for Rent in Highlands, Winter Springs, FL

Average rent

$2,075

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475 Macgregor Rd #NA - Photo 1 of 1

7h ago

Highlands house for rent in Winter Springs

475 Macgregor Rd #NA, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,500

House for rent

Available Jul 1

Description

Amazing 3 bedroom, 2 bathroom house in Winter Springs. Amenities included: central air, central heat, dishwasher, appliance, storage, washer dryer hook-ups, yard, and community pool. No Utilities included. Is not pet friendly. Date Available: Jul 1st 2026. $2,500/month rent. $5,000 security deposit required. Please submit the form on this page or contact Vikas at 321-304-1732 to learn more. This property is managed by a responsible landlord using Avail landlord software.

105 Keith Ct - Photo 1 of 1

5d+ ago

Highlands townhouse for rent in Winter Springs

105 Keith Ct, Winter Springs, FL 32708

Outdoor space | Garage parking | Swimming pool

3 beds

2.5 baths

$2,150

House for rent

Description

Fabulous. 3/2.5/2 Townhome, with new beautiful laminate flooring, all kitchen appliances Living room with fireplace dining room, fence yard. The Highlands is a carefully planned environmental community in the heart of Central Florida with nature trails, pickle ball / tennis courts, lakes, playgrounds, along with a welcoming community center with family-friendly pools and picnic areas. Some others the best schools, shopping and restaurants. Call to schedule you tour. Don't Miss It. Will Not Last! RV / LB

542 Colonnades Cv - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2 beds

2 baths

$1,775

House for rent

Available May 29

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. Interested in this home? You clearly have exceptional taste. This charming 2.0-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! Some images have been virtually staged to help showcase the potential o

1250 N Brassie Dr #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

$1,975 - 2 Bedroom 1 Bathroom House In Winter Springs With large lot

1250 N Brassie Dr #NA, Winter Springs, FL 32708

In-unit laundry | Assigned parking | Air conditioning

2 beds

1 bath

$1,975

House for rent

Available Jun 20

Description

Updated 2 bedroom, 1 bathroom house in Winter Springs. Amenities included: central air, central heat, dishwasher, stainless steel appliance, updated kitchen, updated bathroom, and washer dryer. Utilities included: water and landscaping. Is not pet friendly. Date Available: Jun 20th 2026. $1,975/month rent. $1000 security deposit required along with first and last months rent. Please submit the form on this page or contact Natasha at 321-274-2017 to learn more. This property is managed by a responsible landlord using Avail landlord software.

44 S Cortez Ave - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

44 S Cortez Ave, Winter Springs, FL 32708

Outdoor space | Storage | Ceiling fan

3 beds

2 baths

$2,495

$2,395

Price drop

House for rent

Available Jun 10

Description

Beautiful 3/2 Home in Winter Springs! This recently refreshed single-family home offers three bedrooms and two bathrooms with brand new flooring and fresh interior paint throughout. Both bathrooms feature new cabinets and brand new tile work, and the property includes a brand new air conditioner for added comfort. Ceiling fans are installed for improved circulation, and washer/dryer hook-ups are available for laundry convenience. Outside, a fenced backyard and an on-site shed provide extra storage. Located in Winter Springs, this home combines modern updates with practical

Nearby rental good for eco-living

Nearby rental good for pet owners

Listings within 5 miles
224 Bitterwood St - Photo 1 of 1

1d ago

North Orlando house for rent in Winter Springs

224 Bitterwood St, Winter Springs, FL 32708

In-unit laundry | On-site management

3 beds

2 baths

$2,399

$2,299

Price drop

House for rent

Available Jun 5

Description

Welcome home! This charming 3-bedroom, 2-bath home is available for immediate move-in. Located in Winter Springs, the property offers a functional layout, spacious living areas, generously sized bedrooms, and a well-equipped kitchen with plenty of cabinet and counter space. The first bedroom is scheduled to be painted next week, providing a fresh update for the new resident. All applicants are required to complete a credit and background screening. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per mo

213 S Moss Rd #213 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Springs

213 S Moss Rd, Winter Springs, FL 32708

213 S Moss Rd #213, Winter Springs, FL 32708

2 beds

1.5 baths

$1,495

House for rent

Available May 25

Description

Property Id: 2567526 Here is a professional, conversion-focused TurboTenant description tailored to the specific details of the property at 213 S Moss Rd. It uses clear spacing and bullet points for high readability on mobile devices, with absolutely no emojis. Charming 2-Bedroom Rental in the Heart of Winter SpringsWelcome to 213 S Moss Road, a well-designed 2-bedroom property offering the perfect blend of comfort and convenience in Winter Springs. This rental features a highly functional layout that optimizes space and natural light, making it an excellent choice for an

213 S Moss Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

House for rent

Description

Sweet Home

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137 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

2 beds

2 baths

$1,515

House for rent

Description

MOVE IN SPECIAL: $200 OFF FIRST MONTH'S RENT. 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 communi

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

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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.

228 Bitterwood St - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

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

228 Bitterwood St, Winter Springs, FL 32708

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$2,305

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 technolog

828 Shell Ln - Photo 1 of 1

5d+ ago

House for rent in Longwood

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

828 Shell Ln, Longwood, FL 32750

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$2,270

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 technolog

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

212 S Cortez Ave #NA - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

Winter Springs Pool Home

212 S Cortez Ave #NA, Winter Springs, FL 32708

In-unit laundry | Outdoor space | Assigned parking

4 beds

3 baths

$2,400

House for rent

Available Jun 15

Description

Amazing 4 bedroom, 3 bathroom Furnished house in Winter Springs. Huge fenced in backyard in a safe neighborhood and large screend in patio perfect for summer in Central Florida! This house is NOT Fully furnished, bed frames and some outdoor furniture available. Amenities provided: central air, central heat, dishwasher, hardwood floors, pool, stainless steel appliance, updated kitchen, washer dryer, and yard. Tenant pays electric, water and Wifi. (water bill can be high due to pool -so budget for around $3k/mo total expenses -but landlord pays for lawn care, pest control an

118 Sundance Ct - Photo 1 of 1

3d ago

House for rent in Winter Springs

118 Sundance Ct, Winter Springs, FL 32708

In-unit laundry | Storage | Garage parking

3 beds

2 baths

$2,149

House for rent

Available Jun 4

Description

Introducing a delightful 3-bedroom, 2-bathroom home nestled in the heart of Winter Springs! This inviting residence features a spacious family room adorned with a blend of tasteful tile and plush carpet flooring throughout. The well-equipped kitchen comes complete with a refrigerator, range, dishwasher, and microwave, as well as a cozy eat-in area perfect for casual dining. Retreat to the generously-sized master bedroom, which boasts a walk-in closet and a private en-suite bathroom for added convenience and comfort. Additional amenities include a washer/dryer within the ho

116 S Moss Rd - Photo 1 of 1

2d ago

North Orlando house for rent in Winter Springs

4 Bedroom Pet-Friendly Home in WINTER SPRINGS, FL with Main Street Renewal

116 S Moss Rd, Winter Springs, FL 32708

Swimming pool

4 beds

2 baths

$2,590

House for rent

Description

Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply. We do not advertise on or ask for payments via check, cash, wire transfer, or cash apps. Contact us to schedule a showing.

109 N Alderwood St - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

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

109 N Alderwood St, Winter Springs, FL 32708

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$2,155

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 technolog

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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

$2,455

House for rent

Available Jun 5

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. Interested in this home? You clearly have exceptional taste. This charming 3-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 Association (HOA) for this home may have a separate applic

241 Holiday Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

241 Holiday Ln, Winter Spgs, FL 32708

Outdoor space | Garage parking | High ceilings

3 beds

2 baths

$2,545

House for rent

Available Jun 12

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. 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! Some images have been virtually staged to help showcase the potential o

1412 Oberlin Ter - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1412 Oberlin Ter, Lake Mary, FL 32746

Deck | Garage parking | High ceilings

3 beds

2.5 baths

$2,465

$2,310

Price drop

House for rent

Available Jul 6

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 is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist today. Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyda

439 E Springtree Way - Photo 1 of 1

2d ago

Our team has verified this company

Verified

439 E Springtree Way, Lake Mary, FL 32746

On-site laundry | Outdoor space | Garage parking

3 beds

2 baths

$2,490

House for rent

Available Aug 24

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

321 Alba Ln - Photo 1 of 1

4h ago

Our team has verified this company

Verified

321 Alba Ln, Lake Mary, FL 32746

On-site laundry | Outdoor space | Garage parking

3 beds

2 baths

$3,530

House for rent

Available Jul 10

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

1933 Varick Way - Photo 1 of 1
3D tour

5d+ ago

Our team has verified this company

Verified

1933 Varick Way, Casselberry, FL 32707

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$2,850

$2,700

Price drop

House for rent

Available Jun 10

Description

This property is available. Please inquire on this site to schedule a showing. Discover this charming rental home located at 1933 Varick Way in the highly desirable Casselberry, FL area. This solar-powered residence offers significant monthly electricity savings. The property features attractive curb appeal with a well-maintained lawn, neatly trimmed hedges, and a paver walkway leading to a welcoming front porch, creating an inviting atmosphere from the moment you arrive. Inside, you will find an open-concept living and dining area with rich hardwood laminate flooring and

147 Burns Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

147 Burns Ave Longwood, FL 32750

147 Burns Ave, Longwood, FL 32750

Outdoor space | Garage parking

4 beds

1.5 baths

$2,085

$2,045

Price drop

House for rent

Available Jun 3

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 $2189.90. That covers your base rent, $2045.00 + 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. Taking time for yourself will be even

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Home > House Rentals in Winter Springs > Highlands Houses For Rent
Updated: June 22, 2026

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