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Houses for Rent in Windsong, Winter Park, FL

Average rent

$2,970

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2011 Howard Dr - Photo 1 of 1

4d ago

House for rent in Winter Park

2011 Howard Dr, Winter Park, FL 32789

In-unit laundry | Outdoor space | On-site management

3 beds

2 baths

$2,999

House for rent

Available Apr 16

Description

Check out this Winter Park gem near Lake Sue! This 3br/2ba home features a modern kitchen with granite and stainless steel, wood floors, and a private backyard oasis (landscaping included). Perfect for commuters or remote workers, it boasts an oversized 3rd bedroom/office and is minutes from Park Ave and Audubon Park. Zoned for Audubon K-8 and Winter Park High. Every applicant should apply separately. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy

1814 Barker Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1814 Barker Dr, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

5 beds

4 baths

$11,000

House for rent

Description

Property Status: Active Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a reclaimed Chicago brick fireplace and full-length sliders opening to a resort-style lanai with summer kitchen, wood ceiling, and recessed lighting. Step ou

1815 Barker Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1815 Barker Dr, Winter Park, FL 32789

In-unit laundry | Outdoor space | Furnished

4 beds

2 baths

$4,000

House for rent

Description

Property Status: Active Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems, and the scenic Chain of Lakes, this home is perfect for professionals, creatives, and families seeking a refined long-term

1850 Whitehall Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

3 beds

2 baths

$3,475

House for rent

Description

This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The backyard also has a gazebo, is totally fenced in and has lots of room to roam. Conveniently located between Baldwin Park and Winter Parks Park Avenue. Winter Park School district. Sorry

1947 Summerfield Rd - Photo 1 of 1

3d ago

House for rent in Winter Park

3 beds

2 baths

$2,699

House for rent

Available Apr 17

Description

Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act now! This one won't last long! All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master re

2115 Sycamore Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2115 Sycamore Dr, Winter Park, FL 32789

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$3,500

House for rent

Description

Property Status: Active Updated Charming 4 Bed/2 Bath mid-century home located in Northwood Terrace/Audubon Park (just across the street from Baldwin Park). You will love the large lot .34 Acres with it botanical garden, meditation area, a patio with a raised HOT Tub (perfect for a starry night) and plenty of privacy with all the lush foliage. The front door opens to a great room where the kitchen, living area, dining room, and family room are all open to each other. The Hurricane resistant double panned windows offer gorgeous outdoor views, and invite natural light into e

Nearby rental good for eco-living

Nearby rental good for pet owners

3867 Ethan Ln - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

Townhouse - ORLANDO, FL

3867 Ethan Ln, Orlando, FL 32814

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$3,850

House for rent

Description

Property Status: Active Stylish, move-in ready townhome in the heart of Baldwin Park! This well-appointed two-story home offers three bedrooms, two and a half baths, and 1,632 SF of thoughtfully designed living space. The remodeled kitchen is a true showstopper — featuring modern finishes and sleek black stainless steel appliances, it opens seamlessly to a generous living room with warm hardwood floors throughout. Upstairs, the spacious primary suite includes an en suite bath with double sink vanity and a walk-in closet, while two additional guest bedrooms share a well-app

1667 Mizell Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

1667 Mizell Ave, Winter Park, FL 32789

Outdoor space | Dishwasher | Oven

3 beds

3 baths

$3,995

House for rent

Description

Minimum Deposit $3995. Monthly Rent $3995. Available June 1st! Contact Polina at (407) 897-5400 or email **** to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established. Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and style. As you step inside, you'll immediately be captivated by the character and warmth this home exudes. The spacious living areas boast detailed archways, adding a touch of

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Listings within 5 miles
200 Saint Andrews Blvd #1803 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Park

200 Saint Andrews Blvd #1803, Winter Park, FL 32792

On-site laundry | Outdoor space | Assigned parking

2 beds

1.5 baths

$1,499

House for rent

Available Jan 7

Description

This property is managed by Amy Spano at ext. 224. 2-bedroom, 1.5-bathroom, two-story townhouse in Four Seasons Condos of Winter Park. This well maintained townhouse includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with built-in blinds that open to a fenced patio. You will find a neutral color palette throughout the townhouse. Open and fenced-in

4307 Corrine Dr - Photo 1 of 1

5d+ ago

Baldwin Park townhouse for rent in Orlando

Townhouse - ORLANDO, FL

4307 Corrine Dr, Orlando, FL 32814

In-unit laundry | Storage | Garage parking

3 beds

2.5 baths

$3,775

House for rent

Description

Property Status: Active Welcome to 4307 Corrine Drive, a well-maintained townhome ideally located in one of Orlando’s most desirable and walkable areas. This charming residence offers a functional and comfortable layout with abundant natural light throughout the main living spaces, creating a warm and inviting atmosphere. The kitchen provides ample cabinetry and workspace, opening seamlessly to the living and dining areas—perfect for both everyday living and entertaining. Upstairs, the bedrooms offer privacy and generous storage, making the home both practical and livable

2619 Marble Ave - Photo 1 of 1

5d+ ago

House for rent in Orlando

2619 Marble Ave.

2619 Marble Ave, Orlando, FL 32803

In-unit laundry | Outdoor space | Storage

1 bed

1 bath

$1,500

House for rent

Description

Welcome to your charming 600 square foot home in Orlando, FL! This delightful house, built in 1955, offers a cozy and inviting living space with all the essential amenities. Step inside and discover a well-designed layout featuring 1 bedroom and 1 bathroom, perfect for those seeking a comfortable and manageable home. As you enter, you will be greeted by a spacious living-room with a ceiling fan, creating a cool and relaxed atmosphere. The kitchen is equipped with a refrigerator, range, microwave and granite countertops, providing a stylish and functional space for all you

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504 Saint Dunstan Way - Photo 1 of 1

2d ago

Our team has verified this company

Verified

504 Saint Dunstan Way, Winter Park, FL 32792

On-site laundry | Outdoor space | Swimming pool

3 beds

2 baths

$3,025

House for rent

Available Jun 17

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

2029 Taylor Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2029 Taylor Ave, Winter Park, FL 32792

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

4 beds

3 baths

$2,655

$2,525

Price drop

House for rent

Available Mar 7

Description

Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99). HOAs may also charge mandatory application and amenity fees, where applicable, which must be paid directly to the HOA. For a comprehensive overview of all potentia

5469 Decatur St - Photo 1 of 1

5d+ ago

House for rent in Orlando

2 beds

1 bath

$1,175

House for rent

Description

Semoran Club: 2 bedroom 1 bath triplex located in the Semoran club subdivision. Backs up to conservation pond. Community pool. It has a private patio and courtyard in the front. Ceramic tile in living area and carpets in the 2 bedrooms. Stack able washer/dryer. Open kitchen. Next street over is Lake Baldwin and the back of Baldwin Park. Excellent schools! ***NO PETS*** Disclosure: The water would be a flat rate of $30.00 per month aside from the rent. Applications will ONLY be processed if you have viewed the inside of the home, submitted all applications and dropped o

1400 Park Lake St - Photo 1 of 1

1d ago

Colonialtown North house for rent in Orlando

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$3,200

House for rent

Description

3 bedroom, 2.5 bath home for lease in the highly desirable Colonialtown North / Mills 50 area. Ideally located just steps from Publix and the vibrant mix of local shops, restaurants, cafés, and nightlife along Mills 50. This home features tile and hard flooring throughout—no carpet—plus a washer and dryer (included) conveniently located in the one-car garage. Enjoy a small, fenced-in paved yard, perfect for low-maintenance outdoor living. Zoned for a highly sought-after school district and within walking distance to the Mills 50 dining and entertainment scene. Colonialtown

6003 Oleander Dr - Photo 1 of 1

1d ago

House for rent in Azalea Park

6003 Oleander Dr, Azalea Park, FL 32807

In-unit laundry | Dishwasher

2 beds

1.5 baths

$1,700

House for rent

Description

Beautiful 2-bedroom, 1.5-bath newly renovated half duplex located off SR436 between Lake Underhill Rd and Colonial Dr. This home is in move-in condition with fresh interior paint, tiled flooring throughout, and a partially fenced yard. The kitchen offers standard appliances, ample counter space, and updated cabinetry. A washer and dryer are included for your convenience. Conveniently located near SR408, major highways, shopping, and restaurants. No animals allowed. Showings by appointment only. Call now to schedule your viewing. Call Dinah at 407-592-8626 Email: ****

2530 Passamonte Dr #10E - Photo 1 of 1

3d ago

Townhouse for rent in Winter Park

Condominium - WINTER PARK, FL

2530 Passamonte Dr #10E, Winter Park, FL 32792

In-unit laundry | Garage parking | High ceilings

3 beds

2.5 baths

$2,600

House for rent

Description

Property Status: Active REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary school. Quiet neighbors. The home comes unfurnished. Amenities - dog park and kids play area. Walking distance to Walmart and 5 minutes away to Costco, Publix an

1521 Chestnut Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1521 Chestnut Ave, Winter Park, FL 32789

Outdoor space | Garage parking | Swimming pool

4 beds

3 baths

$6,500

House for rent

Description

Property Status: Pending Gorgeous single-family home in the "tree streets" of Winter Park now available for rent or purchase. Private pool, two car garage, fabulous location and newer construction! Don't wait! Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for toda

438 Lakeview Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

House for rent

Description

Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete with a cozy firepit and large privacy bushes that create a secluded, tranquil retreat—ideal for relaxing evenings or entertaining guests. With a deeded dock and boat lift, you’ll have

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701 Kings Cove Ct - Photo 1 of 1

5d+ ago

House for rent in Azalea Park

701 Kings Cove Ct, Azalea Park, FL 32807

Garage parking | Carpet | Ceiling fan

2 beds

2 baths

$1,695

House for rent

Available Apr 13

Description

A Virtual Tour Video Is Available On Our WEBSITE! This property is managed by Lionel Hebert at ext. 233. 2-bedroom, 2-bath home located in the Azalea Park near Colonial and Sr436. The home features a spacious living room, dining area, and a kitchen equipped with a refrigerator with icemaker, stove, dishwasher, and pantry. Additional amenities include a two-car garage and a dedicated laundry area with washer and dryer hookups. 1440 total sq. ft., with 1008 sq. ft under air conditioning. All information is deemed reliable, but not guaranteed. Wilson Management Group does n

945 La Salle Ave - Photo 1 of 1

5d+ ago

Colonialtown North house for rent in Orlando

945 La Salle Ave, Orlando, FL 32803

In-unit laundry | Outdoor space

2 beds

2 baths

$1,695

House for rent

Description

Discover this well-maintained 2-bedroom, 2-bath home in Orlando, FL. The property includes a covered carport and a large laundry room with washer and dryer hookups for convenience. Lawn care and water are included, simplifying maintenance and monthly expenses. Thoughtfully laid out, the home offers practical living space and functional amenities in a desirable location.

1803 Pineview Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1803 Pineview Cir, Winter Park, FL 32792

In-unit laundry | Outdoor space | Hardwood floor

2 beds

1 bath

$1,975

House for rent

Description

Property Status: Active This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult (18+) **Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: - Drivers License

1137 Oaks Blvd - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1137 Oaks Blvd, Winter Park, FL 32789

In-unit laundry | Outdoor space | Dishwasher

2 beds

1.5 baths

$2,695

House for rent

Description

Property Status: Active Rarely available neighborhood for rentals, this 2 bedroom 1 and a half bath house is surrounded by multi-million dollar homes. Large back yard is totally fenced for kids or pets. Zoned for Winter Park's finest schools and located just off Park Avenue for easy access to shopping and restaurants. Shorter term lease is negotiable. All appliances are in place, including washer/dryer. Don't miss this quaint home on a picturesque brick lined street. Office Phone: (407) 353-0106 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by

540 W Comstock Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Park

Single Family Residence - WINTER PARK, FL

540 W Comstock Ave, Winter Park, FL 32789

Ceiling fan

3 beds

1 bath

$2,900

House for rent

Description

Property Status: Active Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior designed for today’s renter, delivering comfort, functionality, and style in a true turnkey living experience. Ideally located just minutes from Park Avenue,

1034 Herman Avenue - Photo 1 of 1

5d+ ago

House for rent in Orlando

1034 Herman Avenue, Orlando, FL 32803

In-unit laundry | Garden | Storage

3 beds

2.5 baths

$3,500

House for rent

Available Sep 1

Description

Modern 2021-Built Home Steps from Baldwin Park | 3 Bed / 2.5 Bath Welcome to your next home in one of Orlando’s most desirable areas—just a short walk from Baldwin Park! Built in 2021, this beautifully designed property offers a fresh, modern feel with high-end finishes throughout. From the moment you walk in, you’ll notice the attention to detail and open, inviting layout. Home Features: -Spacious open-concept living area with abundant natural light -Stunning oversized kitchen island—perfect for cooking, entertaining, or working from home -Modern kitchen with upgraded

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Windsong Houses For Rent
Updated: April 21, 2026

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💰Best rent deal1947 Summerfield Rd
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