Houses Under $2000 for Rent in Winter Park, FL

18 rentals

Sort:

Recommended

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
A large private room with plenty of closet space and fully furnised is available in a warm 3 bedroom 2 bath house. This cosy and spacies one lever house has a recenty renovated kitchen and has tile fl

$950/mo

1 bed1 bath1,768 sq ft

7552 Bent Bow Trl, Winter Park, FL 32792

Cats welcome • Laundry in unit • A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Winter Park area studio apt 1/1 nice area include Utilities in the rent laundty in unit, parking spot available Owner pays for water, cable,Internet, and Electric. cats allowed. Not Smoking 1 ye

$1,300/mo

1 bed1 bath620 sq ft

2037 Linden Rd, Winter Park, FL 32792

Cats welcome • Laundry in unit • A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
1 MONTH FREE with a 14-month lease! Limited time only! Welcome to the Winter Park 3/2 with Fenced Yard - A stunning home located in the heart of Winter Park, FL. This property boasts three spacious be

$1,881/mo

3 beds2 baths1,300 sq ft

3392 Bougainvillea Dr, Winter Park, FL 32792

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
LOOKING FOR ROOMMATE! One fully furnished one-bedroom with a shared kitchen, living room, and bathroom in this 3/2 home for rent. Close to bus routes, restaurants, grocery stores, and other amenities.

$950/mo

3 beds2 baths1,906 sq ft

760 Northwood Cir, Winter Park, FL 32789

Parking • A/C • Somewhat walkable

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Welcome to this solid masonry home in Winter Park offering 1,409 square feet of comfortable living space. Built in 1969 and thoughtfully maintained, the home sits on a spacious 10,062 square foot lot.

$1,885/mo

3 beds2 baths1,409 sq ft

2111 Conifer Ave, Winter Park, FL 32792

Pets welcome • Parking • A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
AVAILABLE NOW. JUST REDUCED FOR QUICK MOVE IN! Welcome to Bear Gully Forest, conveniently located in Winter Park- right off Aloma across from Trinity Prep! This pretty two-story home boasts 4 Bedrooms

$2,000/mo

4 beds2 baths1,800 sq ft

5587 Pats Pt, Winter Park, FL 32792

Pets welcome • Parking • Dishwasher

Property at 2326 Wellington Blvd, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,295/mo

1 bed1 bath755 sq ft

2326 Wellington Blvd, Winter Park, FL 32789

Property at 668 Montego Bay Ct, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,800/mo

2 beds2 baths1,037 sq ft

668 Montego Bay Ct, Winter Park, FL 32792

Property at 3136 Patel Dr, Winter Park, FL, 32792, 3 beds, 2 baths, [object Object]

$1,825/mo

3 beds2 baths1,300 sq ft

3136 Patel Dr, Winter Park, FL 32792

Property at 7328 Forest Hill Ct, Winter Park, FL, 32792, 2 beds, 2.5 baths, [object Object]

$1,647/mo

2 beds2.5 baths1,031 sq ft

7328 Forest Hill Ct, Winter Park, FL 32792

Property at 2667 Rook Cv, Winter Park, FL, 32792, 2 beds, 1.5 baths, [object Object]

$1,795/mo

2 beds1.5 baths900 sq ft

2667 Rook Cv, Winter Park, FL 32792

Property at 130 N Center St Unit 2, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,665/mo

1 bed1 bath1,000 sq ft

130 N Center St Unit 2, Winter Park, FL 32789

Property at 7350 Swallow Run, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,650/mo

2 beds2 baths774 sq ft

7350 Swallow Run, Winter Park, FL 32792

Property at 1950 Killarney Dr Unit 2, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,325/mo

1 bed1 bath502 sq ft

1950 Killarney Dr Unit 2, Winter Park, FL 32789

Property at 3651 N Goldenrod Rd Unit F205, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,400/mo

2 beds2 baths840 sq ft

3651 N Goldenrod Rd Unit F205, Winter Park, FL 32792

Property at 3002 Antique Oaks Cir Unit 97, Winter Park, FL, 32792, 1 bed, 1 bath, [object Object]

$1,250/mo

1 bed1 bath750 sq ft

3002 Antique Oaks Cir Unit 97, Winter Park, FL 32792

Property at 1512 Indiana Ave Unit B, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,450/mo

1 bed1 bath960 sq ft

1512 Indiana Ave Unit B, Winter Park, FL 32789

Property at 1902 Azalea Ave, Winter Park, FL, 32792, 3 beds, 2 baths, [object Object]

$1,950/mo

3 beds2 baths1,176 sq ft

1902 Azalea Ave, Winter Park, FL 32792

End of results (Download All)

Here are some rentals close to your search

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Nice in ground pool home with fenced in yard. This home is freshly painted and clean, with new kitchen and ceiling fans. It has all tile floors and a large laundry room. First months rent plus $2249 d

$1,949/mo

4 beds1.5 baths1,450 sq ft

3903 Pine Ridge Rd, Orlando, FL 32808

A/C • Car-dependent • Patio/Balcony

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Perfect for mid-term rentals! Discover the perfect blend of comfort and character in this thoughtfully renovated, stylish studio apartment. With an open living area, a queen-sized bed, and a full bat

$2,000/mo

1 bed1 bath400 sq ft

160 Palmyra Dr Unit 2, Orlando, FL 32807

A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Perfect for mid-term rentals! Step into the perfect blend of charm and comfort in this thoughtfully renovated studio apartment. With its open living area, a cozy queen-sized bed, and a full bathroom,

$2,000/mo

1 bed1 bath275 sq ft

160 Palmyra Dr Unit 3, Orlando, FL 32807

A/C • Patio/Balcony

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Charming cabin-inspired retreat perfect for mid-term rentals! Step into a fresh renovation crafted with equal parts style and functionality. Discover the perfect mix of retro charm and modern conven

$1,750/mo

1 bed1 bath500 sq ft

502 Engel Dr Unit 3, Orlando, FL 32807

A/C • Patio/Balcony

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
Newly renovated studio apartment with garage and laundry. 4 closets with pantry, full kitchen, A/C, heat pump, vaulted ceiling, ceiling fan, Super clean, safe upscale neighborhood Fenced in yard with

$1,380/mo

1 bed1 bath725 sq ft

229 Summerwood Trl, Maitland, FL 32751

Laundry in unit • A/C • Car-dependent

ABOUT THIS HOME
House Under $2000 for Rent in Winter Park:
location, location , location nice 2 bedrooms condo at metrowest on kirkmen road, walking distance from wlmart and restaurants, just 2 mikes from higway 4 owner pays the water, tenant pays the power

$1,595/mo

2 beds1 bath933 sq ft

2528 Robert Trent Jones Dr, Orlando, FL 32835

Pets welcome • Laundry in unit • A/C

Property at 160 Palmyra Dr Unit 4, Orlando, FL, 32807, 1 bed, 1 bath, [object Object]

$2,000/mo

1 bed1 bath575 sq ft

160 Palmyra Dr Unit 4, Orlando, FL 32807

Property at 502 Engel Dr Unit 2, Orlando, FL, 32807, 1 bed, 1 bath, [object Object]

$1,550/mo

1 bed1 bath400 sq ft

502 Engel Dr Unit 2, Orlando, FL 32807

Property at 160 Palmyra Dr Unit 5, Orlando, FL, 32807, 1 bed, 1 bath, [object Object]

$2,000/mo

1 bed1 bath600 sq ft

160 Palmyra Dr Unit 5, Orlando, FL 32807

Property at Wheatley St, Orlando, FL, 32811, 3 beds, 1.5 baths, [object Object]

$840/mo

3 beds1.5 baths— sq ft

Wheatley St, Orlando, FL 32811

Property at 625 Tam O Shanter Dr, Orlando, FL, 32803, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath500 sq ft

625 Tam O Shanter Dr, Orlando, FL 32803

Property at 3037 Condel Dr Unit 3, Orlando, FL, 32812, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath350 sq ft

3037 Condel Dr Unit 3, Orlando, FL 32812

Property at 10012 Trilliums Dr, Orlando, FL, 32825, 3 beds, 2.5 baths, [object Object]

$1,995/mo

3 beds2.5 baths1,949 sq ft

10012 Trilliums Dr, Orlando, FL 32825

Property at 2800 W Concord St, Orlando, FL, 32805, 3 beds, 1 bath, [object Object]

$844/mo

3 beds1 bath864 sq ft

2800 W Concord St, Orlando, FL 32805

Property at 3037 Condel Dr Unit 2, Orlando, FL, 32812, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath525 sq ft

3037 Condel Dr Unit 2, Orlando, FL 32812

Property at 1407 Lantry Ct, Orlando, FL, 32804, 2 beds, 1 bath, [object Object]

$1,900/mo

2 beds1 bath667 sq ft

1407 Lantry Ct, Orlando, FL 32804

Property at 4431 Barley St, Orlando, FL, 32811, 4 beds, 1 bath, [object Object]

$864/mo

4 beds1 bath1,026 sq ft

4431 Barley St, Orlando, FL 32811

Property at 115 Orienta Dr, Altamonte Springs, FL, 32701, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths1,080 sq ft

115 Orienta Dr, Altamonte Springs, FL 32701

Property at 317 San Gabriel St, Winter Springs, FL, 32708, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths1,100 sq ft

317 San Gabriel St, Winter Springs, FL 32708

Property at 309 San Gabriel St, Winter Springs, FL, 32708, 3 beds, 2 baths, [object Object]

$1,995/mo

3 beds2 baths1,102 sq ft

309 San Gabriel St, Winter Springs, FL 32708

Based on information submitted to the MLS GRID as of Mon Sep 22 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

More to explore in Winter Park, FL

Property Types
Bedrooms
Amenities
Price

Apartments for rent near Winter Park, FL

Cities
Rental Buildings

Neighborhoods
Zip Codes

Popular rental markets in Florida

Rentals
Apartments

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Houses Under $2000 for Rent in Winter Park, FL

More to explore in Winter Park, FL

Rentals near Winter Park, FL

Cities

Apartments for rent near Winter Park, FL

Popular rental markets in Florida

Related searches in Winter Park, FL