Rentals Under $2000 in Winter Garden, FL

42 rentals

Sort:

Recommended

NEW 13 HRS AGODEAL

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Welcome Home to Ascend Waterleigh Village! Elevate Your Lifestyle! Brand New Apartments. Retreat to a life of ultimate luxury at Ascend Waterleigh Village, a brand-new community offering one, two, an

$1,540+/mo

1 bed1 bath786-987 sq ft

Ascend Waterleigh Village

| 16200 Ascend Village Ln, Winter Garden, FL 34787

44 units available • Pets welcome • A/C

DEAL

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Price shown is Base Rent. Residents are required to pay: At Application: Application Fee ($50.00/applicant, nonrefundable); At Move-in: Admin Fee ($250.00/unit); Security Deposit (Refundable) ($200.0-

$1,604+/mo

1 bed1 bath742-759 sq ft

Windermere Cay

| 8200 Jayme Dr, Winter Garden, FL 34787

7 units available • Pets welcome • Parking

NEW 13 HRS AGO

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Welcome to Palm Crossing. Located in the historic Winter Garden, FL, Palm Crossing is the perfect community to call home. With a collection of modern floorplans paired with a robust list of resort-sty

1 bd: $1,466

2 bd: $1,734 • 3 bd: $1,809

Palm Crossing

| 1240 Winter Garden Vineland Rd, Winter Garden, FL 34787

15 units available • Pets welcome • Parking

NEW 13 HRS AGODEAL

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Step into a world of luxury at Halston Waterleigh, an upscale community in Winter Garden, Florida. Experience exquisite design, abundant natural light, advanced technology, and endless comfort in your

$1,725+/mo

1 bed1 bath769-796 sq ft

Halston Waterleigh

| 10091 Tuller Loop, Winter Garden, FL 34787

24 units available • Car-dependent • Fitness Center

NEW 13 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Take the next step in life at Corban Horizon West. A place that draws inspiration from the warmth of the neighborhood and the endless possibilities that surround it, our homes offer a refreshing exper

$1,756+/mo

1 bed1 bath729-873 sq ft

Corban Horizon West

| 15000 Stratus Loop, Winter Garden, FL 34787

31 units available • Pets welcome • Parking

3 MONTHS FREE

ABOUT THIS HOME
Rentals Under $2000 in Winter Garden, FL
Welcome home to Registry on Grass Lake, our brand-new apartment community that prioritizes a connection to comfort & convenience through designer touches and thorough consideration of your needs. Enjo

$1,574+/mo

1 bed1 bath617-840 sq ft

Registry on Grass Lake

| 14520 Avalon Rd, Winter Garden, FL 34787

196 units available • Pets welcome • Parking

Property at Homestead at Hamlin - 15100 Free Range Run, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,647+/mo

1 bed1 bath627-790 sq ft

Homestead at Hamlin

| 15100 Free Range Run, Winter Garden, FL 34787

Property at Prose Avalon Pointe - 14505 Tristan Cir, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,550+/mo

1 bed1 bath835 sq ft

Prose Avalon Pointe

| 14505 Tristan Cir, Winter Garden, FL 34787

Property at Cortland Independence - 14600 Avenue of the Grvs, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,679+/mo

1 bed1 bath751 sq ft

Cortland Independence

| 14600 Avenue of the Grvs, Winter Garden, FL 34787

Property at The Lodge at Hamlin - 6151 Lake Lodge Dr, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,683+/mo

1 bed1 bath702-854 sq ft

The Lodge at Hamlin

| 6151 Lake Lodge Dr, Winter Garden, FL 34787

Property at The Westerly - 14680 Westerly Dr, Winter Garden, FL, 34787, 0-1 beds, 1 bath, [object Object]

$1,625+/mo

0-1 beds1 bath678-858 sq ft

The Westerly

| 14680 Westerly Dr, Winter Garden, FL 34787

Property at Prose Horizons Village - 16810 Easthampstead Rd, Winter Garden, FL, 34787, 1-2 bed, 1-2 bath, [object Object]

$1,620+/mo

1-2 bed1-2 bath835-1,180 sq ft

Prose Horizons Village

| 16810 Easthampstead Rd, Winter Garden, FL 34787

Property at Country Gardens - 15122 W Colonial Dr, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,750+/mo

2 beds2 baths951 sq ft

Country Gardens

| 15122 W Colonial Dr, Winter Garden, FL 34787

Property at Overture Hamlin - 5620 Hamlin Groves Trl, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,932+/mo

1 bed1 bath758 sq ft

Overture Hamlin

| 5620 Hamlin Groves Trl, Winter Garden, FL 34787

Property at Slate Luxury Apartments - 584 W Bay St, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,735+/mo

1 bed1 bath622 sq ft

Slate Luxury Apartments

| 584 W Bay St, Winter Garden, FL 34787

Property at The Haven at Lake Britt - 15145 Havencrest Cir, Winter Garden, FL, 34787, 0-1 beds, 1 bath, [object Object]

$1,655+/mo

0-1 beds1 bath680-830 sq ft

The Haven at Lake Britt

| 15145 Havencrest Cir, Winter Garden, FL 34787

Property at Apollo Apartments - 7000 Kiran Patel Dr, Winter Garden, FL, 34787, 0-2 beds, 1-2 bath, [object Object]

$1,579+/mo

0-2 beds1-2 bath653-1,051 sq ft

Apollo Apartments

| 7000 Kiran Patel Dr, Winter Garden, FL 34787

Property at 14200 Avalon Rd Unit 430, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,750/mo

2 beds2 baths1,288 sq ft

14200 Avalon Rd Unit 430, Winter Garden, FL 34787

Property at 304 Southern Pecan Cir #203, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,645/mo

1 bed1 bath942 sq ft

304 Southern Pecan Cir #203, Winter Garden, FL 34787

Property at 236 E Lafayette St Unit 1, Winter Garden, FL, 34787, 2 beds, 1 bath, [object Object]

$1,750/mo

2 beds1 bath— sq ft

236 E Lafayette St Unit 1, Winter Garden, FL 34787

Property at 131 Southern Pecan Cir #201, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath738 sq ft

131 Southern Pecan Cir #201, Winter Garden, FL 34787

Property at 224 W Cypress St, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$1,975/mo

3 beds2 baths1,000 sq ft

224 W Cypress St, Winter Garden, FL 34787

Property at 312 Eron Way #4, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,600/mo

1 bed1 bath720 sq ft

312 Eron Way #4, Winter Garden, FL 34787

Property at 2895 Haze Rd Unit B, Clermont, FL, 34714, 1 bed, 1 bath, [object Object]

$1,300/mo

1 bed1 bath480 sq ft

2895 Haze Rd Unit B, Clermont, FL 34714

Property at 96 Windtree Ln #203, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,800/mo

2 beds2 baths918 sq ft

96 Windtree Ln #203, Winter Garden, FL 34787

Property at 162 Windtree Ln #204, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,650/mo

2 beds2 baths918 sq ft

162 Windtree Ln #204, Winter Garden, FL 34787

Property at 64 Windtree Ln #203, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,550/mo

2 beds2 baths918 sq ft

64 Windtree Ln #203, Winter Garden, FL 34787

Property at 7121 Blue Indigo Cres, Winter Garden, FL, 34787, 0 beds, 1 bath, [object Object]

$1,800/mo

0 beds1 bath750 sq ft

7121 Blue Indigo Cres, Winter Garden, FL 34787

Property at 14843 Astrolyn St, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$1,999/mo

3 beds2 baths1,260 sq ft

14843 Astrolyn St, Winter Garden, FL 34787

Property at 502 Dunbar Ave, Winter Garden, FL, 34787, 2 beds, 1 bath, [object Object]

$1,525/mo

2 beds1 bath816 sq ft

502 Dunbar Ave, Winter Garden, FL 34787

Property at 505 Varsity St, Winter Garden, FL, 34787, 2 beds, 1 bath, [object Object]

$1,749/mo

2 beds1 bath780 sq ft

505 Varsity St, Winter Garden, FL 34787

Property at 5652 Lemon Grass St Unit B, Oakland, FL, 34787, 1 bed, 1 bath, [object Object]

$1,400/mo

1 bed1 bath480 sq ft

5652 Lemon Grass St Unit B, Oakland, FL 34787

Property at 9223 Vintage Hills Way, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,992/mo

1 bed1 bath765 sq ft

9223 Vintage Hills Way, Winter Garden, FL 34787

Property at 16071 Micelli Dr, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,267/mo

1 bed1 bath568 sq ft

16071 Micelli Dr, Winter Garden, FL 34787

Property at 5135 Lake Hamlin Trl, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,650/mo

1 bed1 bath624 sq ft

5135 Lake Hamlin Trl, Winter Garden, FL 34787

Property at 417 Southern Pecan Cir, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,700/mo

1 bed1 bath838 sq ft

417 Southern Pecan Cir, Winter Garden, FL 34787

Property at The Palisades Condominium - 14200 Avalon Rd, Winter Garden, FL, 34787, 2-3 beds, 2 baths, [object Object]

$1,800+/mo

2-3 beds2 baths1,203-1,288 sq ft

The Palisades Condominium

| 14200 Avalon Rd, Winter Garden, FL 34787

Property at 6049 Shavasana Rd, Clermont, FL, 34714, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath700 sq ft

6049 Shavasana Rd, Clermont, FL 34714

Property at 174 Windtree Ln, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,595/mo

2 beds2 baths918 sq ft

174 Windtree Ln, Winter Garden, FL 34787

Property at 115 Windtree Ln, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$1,450/mo

2 beds2 baths918 sq ft

115 Windtree Ln, Winter Garden, FL 34787

Property at 2693 Armstrong Ave Unit B, Clermont, FL, 34714, 1 bed, 1 bath, [object Object]

$1,400/mo

1 bed1 bath386 sq ft

2693 Armstrong Ave Unit B, Clermont, FL 34714

Viewing page 1 of 2

Based on information submitted to the MLS GRID as of Fri Jan 02 2026. 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 Garden, FL

Property Types
Bedrooms
Amenities
Price

Apartments for rent near Winter Garden, FL

Cities
Rental Buildings

Neighborhoods
Zip Codes

Popular rental markets in Florida

Rentals
Apartments

Related searches in Winter Garden, FL

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

Affiliated Business

Countries

United States

Canada

Updated September 2025: 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, 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.

Rentals Under $2000 in Winter Garden, FL

More to explore in Winter Garden, FL

Rentals near Winter Garden, FL

Cities

Apartments for rent near Winter Garden, FL

Popular rental markets in Florida

Related searches in Winter Garden, FL